Online citations, reference lists, and bibliographies.
← Back to Search

Recent Trends In Cys- And Ser/Thr-based Synthetic Strategies For The Elaboration Of Peptide Constructs.

Jean-Christophe M. Monbaliu, A. Katritzky
Published 2012 · Medicine, Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Recent conceptual advances in the chemical synthesis of peptide constructs are described, encompassing native chemical ligation (i.e. the chemoselective covalent condensation of unprotected peptide segments) and O-, S-acyl isopeptide strategies (i.e. internal O,S-to-N acyl transfer within peptides).
This paper references
10.1021/ol300557g
Synthesis of the bacteriocin glycopeptide sublancin 168 and S-glycosylated variants.
Yves S Y Hsieh (2012)
10.1016/J.TETLET.2004.12.089
Dramatically enhanced N→O acyl migration during the trifluoroacetic acid-based deprotection step in solid phase peptide synthesis
L. A. Carpino (2005)
10.1016/j.drudis.2009.10.009
Synthetic therapeutic peptides: science and market.
P. Vlieghe (2010)
10.1021/jm201332p
Design of β-amyloid aggregation inhibitors from a predicted structural motif.
Paul A. Novick (2012)
10.1021/JA0035654
Tandem ligation of unprotected peptides through thiaprolyl and cysteinyl bonds in water.
J. Tam (2001)
10.1002/marc.201100235
From polyesters to polyamides via O-N acyl migration: an original multi-transfer reaction.
Julien Tailhades (2011)
10.1021/JA000128G
Bidirectional Tandem Pseudoproline Ligations of Proline-Rich Helical Peptides
Z. Miao (2000)
10.1021/OL006691L
Computational studies of the aminolysis of oxoesters and thioesters in aqueous solution
Yang (2000)
10.1016/J.BMCL.2003.09.020
O-N intramolecular acyl migration strategy in water-soluble prodrugs of taxoids.
M. Skwarczynski (2003)
10.1021/ol2002804
Synthesis of thiazolidine thioester peptides and acceleration of native chemical ligation.
J. Dheur (2011)
10.1021/JA970606W
Rotational Barriers of cis/trans Isomerization of Proline Analogues and Their Catalysis by Cyclophilin§
D. Kern (1997)
10.1021/JA961509Q
Pseudo-Prolines as a Solubilizing, Structure-Disrupting Protection Technique in Peptide Synthesis
T. Wöhr (1996)
10.1039/C0SC00381F
Continuous flow multi-step organic synthesis
Damien Webb (2010)
10.1002/anie.201005180
9-Fluorenylmethoxycarbonyl-based solid-phase synthesis of peptide α-thioesters.
F. Mende (2011)
10.1007/s10989-006-9075-7
Industrial Applications of Solid-Phase Peptide Synthesis – A Status Report
M. Verlander (2006)
10.1016/J.TETLET.2010.11.154
Synthesis of the sphingolipid activator protein, saposin C, using an azido-protected O-acyl isopeptide as an aggregation-disrupting element
H. Hojo (2011)
10.1016/S0040-4039(00)96584-5
Peptide synthesis by prior thiol capture—V. The scope and control of disulfide interchange during the acyl transfer step
D. Kemp (1987)
10.1002/anie.201106060
Convergent chemical synthesis of [lysine(24,38,83)] human erythropoietin.
Suhuai Liu (2012)
10.1021/JA0708971
Sugar-assisted ligation in glycoprotein synthesis.
Yuying Yang (2007)
10.1039/b903624e
O-acyl isopeptide method: efficient synthesis of isopeptide segment and application to racemization-free segment condensation.
T. Yoshiya (2009)
10.3998/ARK.5550190.0011.816
Evolution of amide bond formation
M. Joullié (2010)
10.1002/bip.21410
S‐acyl isopeptide method: Use of allyl‐type protective group for improved preparation of thioester‐containing S‐acyl isopeptides by Fmoc‐based SPPS
T. Yoshiya (2011)
10.1002/anie.201105512
Preformed selenoesters enable rapid native chemical ligation at intractable sites.
T. Durek (2011)
10.1021/JA00860A025
Intramolecular S-O and S-N Acetyl Transfer Reactions
R. Martin (1962)
10.1002/psc.1059
Switching from the unfolded to the folded state of the helix‐loop‐helix domain of the Id proteins based on the O‐acyl isopeptide method
S. Kiewitz (2008)
10.1021/JO00360A032
Peptide synthesis by prior thiol capture. 1. A convenient synthesis of 4-hydroxy-6-mercaptodibenzofuran and novel solid-phase synthesis of peptide-derived 4-(acyloxy)-6-mercaptodibenzofurans
D. Kemp (1986)
10.1039/c1ob05740e
Microwave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues.
F. K. Hansen (2011)
10.1002/bip.21455
Native chemical ligation with Nalpha acyl transfer auxiliaries.
John L. Offer (2010)
10.1002/asia.201000760
Theoretical analysis of the detailed mechanism of native chemical ligation reactions.
C. Wang (2011)
10.1002/bip.20136
ON intramolecular acyl migration reaction in the development of prodrugs and the synthesis of difficult sequence‐containing bioactive peptides
Y. Sohma (2004)
10.1007/s10989-006-9059-7
In Situ Neutralization in Boc-chemistry Solid Phase Peptide Synthesis
M. Schnölzer (2006)
10.1016/j.bmcl.2009.09.107
Synthesis of 4-mercapto-L-lysine derivatives: potential building blocks for sequential native chemical ligation.
K. Pasunooti (2009)
10.1021/JA057100V
click peptide based on the O-acyl isopeptide method : Control of Aβ1 42 production from a photo-triggered Aβ1 42 analogue
A. Taniguchi (2006)
10.1021/jo200029e
Synthesis of peptide alkylthioesters using the intramolecular N,S-acyl shift properties of bis(2-sulfanylethyl)amido peptides.
J. Dheur (2011)
10.1002/BIP.20683
Development of O-acyl isopeptide method.
Y. Sohma (2007)
10.1002/anie.201103237
Total chemical synthesis of biologically active vascular endothelial growth factor.
K. Mandal (2011)
10.1039/b906492c
Phosphate-assisted peptide ligation.
Gemma L. Thomas (2009)
10.1002/anie.201001900
Traceless ligation of cysteine peptides using selective deselenization.
N. Metanis (2010)
10.1021/ja804993y
Oxo-ester mediated native chemical ligation: concept and applications.
Qian Wan (2008)
10.1002/ANIE.200454045
Switch peptides in statu nascendi: induction of conformational transitions relevant to degenerative diseases.
M. Mutter (2004)
10.1039/c1cc11964h
Semi-synthesis of a protease-activatable collagen targeting probe.
M. Breurken (2011)
10.1021/JA952790W
Orthogonal Ligation of Unprotected Peptide Segments through Pseudoproline Formation for the Synthesis of HIV-1 Protease Analogs†,‡
C. Liu (1996)
10.1002/anie.201100996
Protein chemical synthesis by ligation of peptide hydrazides.
Ge-Min Fang (2011)
10.1002/anie.200902936
Highly efficient and chemoselective peptide ubiquitylation.
K. S. Ajish Kumar (2009)
Tchertchian, Side Chain extended ligation, WO
N.A.McGrath (2011)
10.1016/J.TET.2011.04.048
Design and synthesis of caged ceramide: UV-responsive ceramide releasing system based on UV-induced amide bond cleavage followed by O―N acyl transfer
Akira Shigenaga (2011)
10.1002/bip.21442
Ligation-desulfurization: a powerful combination in the synthesis of peptides and glycopeptides.
Heike Rohde (2010)
10.1016/J.BMC.2005.06.037
'O-Acyl isopeptide method' for the efficient preparation of amyloid beta peptide 1-42 mutants.
Y. Sohma (2005)
10.1021/JA005885T
Selenocysteine in native chemical ligation and expressed protein ligation.
R. Hondal (2001)
10.1039/c1cc00089f
Recent advances in micro reaction technology.
C. Wiles (2011)
10.1002/anie.200705471
An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation.
J. Blanco-Canosa (2008)
10.1073/PNAS.96.18.10068
Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology.
T. Hackeng (1999)
10.1073/PNAS.0305693101
Total chemical synthesis and electrophysiological characterization of mechanosensitive channels from Escherichia coli and Mycobacterium tuberculosis.
Daniel Clayton (2004)
10.1021/JA00722A071
Peptide racemization mechanism. A kinetic isotope effect as a means of distinguishing enolization from oxazolone formation.
D. Kemp (1970)
10.1023/A:1016231913858
The Importance of Structural Factors on the Rate and the Extent of N,O-acyl Migration in Cyclic and Linear Peptides
R. Oliyai (2004)
10.1016/0040-4039(91)80674-U
Highly enantioselective amide ligation by prior thiol capture
D. Kemp (1991)
10.1055/S-0029-1217827
Chiral Acylation with N-(Protected α-Aminoacyl)benzotriazolesfor Advantageous Syntheses of Peptides and Peptide Conjugates
A. R. Katritzky (2009)
10.1039/C1MD00130B
Solution-phase synthesis of chiral O-acyl isodipeptides
Mirna El Khatib (2011)
10.1002/cbic.200800765
“Click Peptide“: pH‐Triggered in Situ Production and Aggregation of Monomer Aβ1–42
Atsuhiko Taniguchi  (2009)
10.1002/PSC.817
‘Click peptide’: a novel ‘O‐acyl isopeptide method’ for peptide synthesis and chemical biology‐oriented synthesis of amyloid β peptide analogues
Y. Sohma (2006)
10.1016/S0040-4039(98)01868-1
Direct preparation of peptide thioesters using an Fmoc solid-phase method
Xiangqun Li (1998)
10.1021/jp107208q
Energetics of the lighter chalcogen analogues of carboxylic acid esters.
Carol A. Deakyne (2010)
10.1002/CHIN.198126139
INTRAMOLECULAR O,N-ACYL TRANSFER VIA CYCLIC INTERMEDIATES OF NINE AND TWELVE MEMBERS. MODELS FOR EXTENSIONS OF THE AMINE CAPTURE STRATEGY FOR PEPTIDE SYNTHESIS
D. Kemp (1981)
10.1021/cr100048w
Peptide coupling reagents, more than a letter soup.
A. El-faham (2011)
10.1021/CR941170V
Properties and Synthetic Utility of N-Substituted Benzotriazoles.
A. Katritzky (1998)
10.1002/cbic.200700740
A Simple Method for Preparing Peptide C‐Terminal Thioacids and Their Application in Sequential Chemoenzymatic Ligation
Xiao-hong Tan (2008)
10.1021/jm2006029
Continuous flow synthesis. A pharma perspective.
Laia Malet-Sanz (2012)
10.1021/ja301255n
Interrogation of MDM2 phosphorylation in p53 activation using native chemical ligation: the functional role of Ser17 phosphorylation in MDM2 reexamined.
Changyou Zhan (2012)
10.1002/CHEM.200305343
Theoretical insights into the mechanism for thiol/disulfide exchange.
P. Fernandes (2004)
10.1016/j.bmc.2011.01.021
'Click peptide' using production of monomer Aβ from the O-acyl isopeptide: application to assay system of aggregation inhibitors and cellular cytotoxicity.
Y. Sohma (2011)
10.1021/JO00273A008
Peptide synthesis by prior thiol capture. 6. Rates of the disulfide-bond-forming capture reaction and demonstration of the overall strategy by synthesis of the C-terminal 29-peptide sequence of BPTI
N. Fotouhi (1989)
10.1016/S0960-894X(98)00349-7
Syntheses of potent Leu-enkephalin analogs possessing β-hydroxy-α,α-disubstituted-α-amino acid and their characterization to opioid receptors
M. Horikawa (1998)
10.1021/ol300528r
Access to cyclic or branched peptides using bis(2-sulfanylethyl)amido side-chain derivatives of Asp and Glu.
E. Boll (2012)
10.1006/BIOL.2001.0292
Tandem peptide ligation for synthetic and natural biologicals.
J. Tam (2001)
10.1016/0040-4039(81)80050-0
Models that demonstrate peptide bond formation by prior thiol capture--II capture by organomercury derivatives
D. Kemp (1981)
10.1039/b700141j
Total chemical synthesis of proteins.
S. Kent (2009)
10.1021/ar200081s
Chemoselectivity in Chemical Biology: Acyl Transfer Reactions with Sulfur and Selenium
Nicholas A. McGrath (2011)
10.1111/J.1432-1033.2004.03978.X
Expressed protein ligation. Method and applications.
R. David (2004)
10.1002/(SICI)1097-0282(19981015)46:5<319::AID-BIP3>3.0.CO;2-S
Methionine ligation strategy in the biomimetic synthesis of parathyroid hormones.
J. Tam (1998)
10.1351/PAC-CON-08-08-11
Kinetics and mechanism of the aminolysis of thioesters and thiocarbonates in solution
Enrique A. Castro (2009)
10.1021/JO00360A033
Peptide synthesis by prior thiol capture. 2. Design of templates for intramolecular O,N-acyl transfer. 4,6-Disubstituted dibenzofurans as optimal spacing elements
D. Kemp (1986)
10.1002/cbic.201000330
Chemical Synthesis and Structure of the Prokineticin Bv8
R. V. Morales (2010)
10.1016/J.TETLET.2004.06.059
Design and synthesis of a novel water-soluble Aβ1-42 isopeptide: an efficient strategy for the preparation of Alzheimer's disease-related peptide, Aβ1-42, via O–N intramolecular acyl migration reaction
Y. Sohma (2004)
10.1021/ol203407z
Synthesis of a dicarba analogue of human β-defensin-1 using a combined ring closing metathesis--native chemical ligation strategy.
Amanda M. Heapy (2012)
10.1039/b701677h
Amide bond formation: beyond the myth of coupling reagents.
Eric Valeur (2009)
10.1002/EJOC.200900024
Internal Cysteine Accelerates Thioester-Based Peptide Ligation
C. Haase (2009)
10.1016/j.peptides.2009.12.001
Controlled in situ preparation of Aβ(1–42) oligomers from the isopeptide “iso-Aβ(1–42)”, physicochemical and biological characterization
Z. Bozsó (2010)
10.1016/J.TETLET.2008.09.126
The concept of internal solubilization in peptide synthesis: ethylene glycol-based protecting groups
L. Kocsis (2008)
10.1016/j.bmc.2009.06.017
Synthesis of amyloid beta peptide 1-42 (E22Delta) click peptide: pH-triggered in situ production of its native form.
H. Wang (2009)
10.1021/JA01605A034
THE DESULFURIZATION OF MERCAPTANS WITH TRIALKYL PHOSPHITES
F. Hoffmann (1956)
10.1021/JO040140H
Fmoc-Based Synthesis of Peptide α-Thioesters Using an Aryl Hydrazine Support†
J. Camarero (2004)
10.1016/J.TETLET.2004.07.162
Synthesis of ‘difficult’ peptide sequences: application of a depsipeptide technique to the Jung–Redemann 10- and 26-mers and the amyloid peptide Aβ(1–42)
L. A. Carpino (2004)
10.1002/anie.200801313
Chemoselective ligation and modification strategies for peptides and proteins.
C. Hackenberger (2008)
10.1016/J.TETLET.2006.03.017
‘O-Acyl isopeptide method’ for the efficient synthesis of difficult sequence-containing peptides: use of ‘O-acyl isodipeptide unit’
Y. Sohma (2006)
10.1039/c2ob07050b
Traceless chemical ligations from O-acyl serine sites.
Mirna El Khatib (2012)
10.1021/ja2111459
Total synthesis of the α-subunit of human glycoprotein hormones: toward fully synthetic homogeneous human follicle-stimulating hormone.
Baptiste Aussedat (2012)
10.1039/B309235F
New isocysteine building blocks and chemoselective peptide ligation.
Christian Dose (2004)
10.1021/JA01576A077
THE REACTION OF THIYL RADICALS WITH TRIALKYL PHOSPHITES1
C. Walling (1957)
10.1021/JO00276A026
Boc-L-Dmt-OH as a fully N,S-blocked cysteine derivative for peptide synthesis by prior thiol capture. Facile conversion of N-terminal Boc-L-Dmt-peptides to H-Cys(Scm)-peptides
D. Kemp (1989)
10.1002/PSC.905
‘O‐Acyl isopeptide method’ for peptide synthesis: Solvent effects in the synthesis of Aβ1–42 isopeptide using ‘O‐acyl isodipeptide unit’
A. Taniguchi (2007)
10.1039/c1cs15214a
Microwave heating in solid-phase peptide synthesis.
Søren L Pedersen (2012)
10.1039/c1ob06397a
Site-specific protein double labeling by expressed protein ligation: applications to repeat proteins.
L. De Rosa (2012)
10.1021/JO052026K
Toward an intimate understanding of the structural properties and conformational preference of oxoesters and thioesters: gas and crystal structure and conformational analysis of dimethyl monothiocarbonate, CH3OC(O)SCH3.
M. Erben (2006)
10.1021/ol102273u
Bis(2-sulfanylethyl)amino native peptide ligation.
N. Ollivier (2010)
10.1039/c0cc03141k
Total chemical synthesis of human proinsulin.
Samuel Luisier (2010)
10.1002/psc.1285
Native chemical ligation of hydrophobic peptides in organic solvents
Marc Dittmann (2010)
10.1016/J.TET.2007.04.105
Diketopiperazines : biological activity and synthesis
M. Martins (2007)
10.1021/JA0266722
Semisynthesis and folding of the potassium channel KcsA.
Francis I Valiyaveetil (2002)
10.1002/psc.1261
Epimerization‐free synthesis of cyclic peptide by use of the O‐acyl isopeptide method
T. Yoshiya (2010)
10.1016/J.TET.2010.01.067
A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides.
J. Chen (2010)
10.1021/JO00060A043
Synthesis of a 39-peptide and a 25-peptide by thiol capture ligations : observation of a 40-fold rate acceleration of the intramolecular O,N-acyl-transfer reaction between peptide fragments bearing only cysteine protective groups
D. Kemp (1993)
10.1002/anie.201005513
Insights into the finer issues of native chemical ligation: an approach to cascade ligations.
Z. Tan (2010)
10.1039/B702284K
"O-acyl isopeptide method" for peptide synthesis: synthesis of forty kinds of "O-acyl isodipeptide unit" Boc-Ser/Thr(Fmoc-Xaa)-OH.
T. Yoshiya (2007)
10.1021/JA052083V
Switch-peptides: controlling self-assembly of amyloid beta-derived peptides in vitro by consecutive triggering of acyl migrations.
Sônia Maria Josino dos Santos (2005)
10.1021/CR990001D
Kinetics and Mechanisms of Reactions of Thiol, Thiono, and Dithio Analogues of Carboxylic Esters with Nucleophiles.
E. Castro (1999)
10.1039/b803248c
Chemical synthesis and semisynthesis of membrane proteins.
Diana Olschewski (2008)
10.1002/CHEM.200304990
Benzotriazole: an ideal synthetic auxiliary.
A. Katritzky (2003)
10.1021/ja910763m
Ester to amide switch peptides provide a simple method for preparing monomeric islet amyloid polypeptide under physiologically relevant conditions and facilitate investigations of amyloid formation.
Ping Cao (2010)
10.1021/JO060914P
Depsipeptide methodology for solid-phase peptide synthesis: circumventing side reactions and development of an automated technique via depsidipeptide units.
Irene Coin (2006)
10.1002/psc.1053
Isopeptide method: development of S‐acyl isopeptide method for the synthesis of difficult sequence‐containing peptides
T. Yoshiya (2008)
10.1002/(SICI)1099-1387(200005)6:5<225::AID-PSC244>3.0.CO;2-T
Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation
A. Clippingdale (2000)
10.1021/JO00367A013
Peptide synthesis by prior thiol capture. IV: Amide bond formation: the effect of a side-chain substituent on the rates of intramolecular O,N-acyl transfer
D. Kemp (1986)
10.1021/JA960398S
EXTENDING THE APPLICABILITY OF NATIVE CHEMICAL LIGATION
Lynne Canne (1996)
10.1021/ja905491p
Dual native chemical ligation at lysine.
Renliang Yang (2009)
10.1021/JA072804L
Native chemical ligation at phenylalanine.
D. Crich (2007)
10.1021/jp7118982
NMR and theoretical calculations: a unified view of the cis/trans isomerization of 2-substituted thiazolidines containing peptides.
H. Jamet (2008)
10.1021/JA020529R
Tandem ligation of multipartite peptides with cell-permeable activity.
K. D. Eom (2003)
10.1111/J.1399-3011.2005.00214.X
'100 years of peptide synthesis': ligation methods for peptide and protein synthesis with applications to beta-peptide assemblies.
T. Kimmerlin (2005)
10.1021/ja204277b
An advance in proline ligation.
Shiying Shang (2011)
10.1016/J.TETLET.2006.09.001
'O-Acyl isopeptide method' : racemization-free segment condensation in solid phase peptide synthesis
T. Yoshiya (2006)
10.1021/JA00444A023
Nonlinear structure-reactivity correlations. Acyl transfer between sulfur and oxygen nucleophiles
D. Hupe (1977)
10.1021/bm200039s
Synthesis and characterization of dendron cross-linked PEG hydrogels as corneal adhesives.
A. Oelker (2011)
10.1016/0040-4039(95)02394-1
Acyl disulfide-mediated intramolecular acylation for orthogonal coupling between unprotected peptide segments. Mechanism and application
C. Liu (1996)
10.1002/cbic.201000168
Protein Synthesis Assisted by Native Chemical Ligation at Leucine
Z. Harpaz (2010)
10.1002/psc.2401
Native chemical ligation in dimethylformamide can be performed chemoselectively without racemization
Marc Dittmann (2012)
10.1021/ol2031284
N-to-C sequential ligation using peptidyl N,N-bis(2-mercaptoethyl)amide building blocks.
Renliang Yang (2012)
10.1039/c003234d
The chemical ligation of selectively S-acylated cysteine peptides to form native peptides via 5-, 11- and 14-membered cyclic transition states.
A. Katritzky (2010)
10.1021/jo1015757
Chemical ligation of S-scylated cysteine peptides to form native peptides via 5-, 11-, and 14-membered cyclic transition states.
A. Katritzky (2011)
10.1021/bc900502z
Remodeling of dynamic structures of HIV-1 envelope proteins leads to synthetic antigen molecules inducing neutralizing antibodies.
Toru Nakahara (2010)
10.1002/cbic.201100025
Click Peptide Concept: O‐Acyl Isopeptide of Islet Amyloid Polypeptide as a Nonaggregative Precursor Molecule
T. Yoshiya (2011)
10.1021/JA00089A001
Chemical Ligation Approach To Form a Peptide Bond between Unprotected Peptide Segments. Concept and Model Study
C. Liu (1994)
10.1002/1521-3765(20010917)7:18<3976::AID-CHEM3976>3.0.CO;2-X
Highly efficient synthesis of peptide-oligonucleotide conjugates: chemoselective oxime and thiazolidine formation.
D. Forget (2001)
10.1007/s10989-008-9154-z
Application of Dmb-Dipeptides in the Fmoc SPPS of Difficult and Aspartimide-Prone Sequences
V. Cardona (2008)
10.1039/c0cc04120c
An investigation into the origin of the dramatically reduced reactivity of peptide-prolyl-thioesters in native chemical ligation.
S. Pollock (2011)
10.1021/JA962656R
Modulation of Reactivity in Native Chemical Ligation through the Use of Thiol Additives
P. Dawson (1997)
10.1021/ja204088a
Fmoc synthesis of peptide thioesters without post-chain-assembly manipulation.
Ji-Shen Zheng (2011)
10.3390/molecules17044158
Ionic Liquid Applications in Peptide Chemistry: Synthesis, Purification and Analytical Characterization Processes
A. Tietze (2012)
10.1016/0960-894X(95)00454-2
Structural Factors affecting the kinetics of O,N-acyl transfer in potential O-peptide prodrugs
R. Oliyai (1995)
10.1021/JA0491836
Toward fully synthetic glycoproteins by ultimately convergent routes: a solution to a long-standing problem.
J. Warren (2004)
10.1038/nrd1133
Large-scale manufacture of peptide therapeutics by chemical synthesis
By G. L. Bray (2003)
10.1021/ja208755j
A carrier protein strategy yields the structure of dalbavancin.
N. J. Economou (2012)
10.1021/JA01494A023
Some Extensions of the Reaction of Trivalent Phosphorus Derivatives with Alkoxy and Thiyl Radicals; a New Synthesis of Thioesters1
C. Walling (1960)
10.1039/B312129A
Novel and efficient synthesis of difficult sequence-containing peptides through O-N intramolecular acyl migration reaction of O-acyl isopeptides.
Y. Sohma (2004)
10.1016/J.TETLET.2003.12.008
O–N-Acyl migration in N-terminal serine-containing peptides: mass spectrometric elucidation and subsequent development of site-directed acylation protocols
L. Mouls (2004)
10.1002/anie.201006686
Total chemical synthesis of an integral membrane enzyme: diacylglycerol kinase from Escherichia coli.
Sunanda Lahiri (2011)
10.1021/JA003265M
Synthesis of peptides and proteins without cysteine residues by native chemical ligation combined with desulfurization.
L. Z. Yan (2001)
10.1002/cbic.200800245
Switch‐Peptides: Design and Characterization of Controllable Super‐Amyloid‐Forming Host–Guest Peptides as Tools for Identifying Anti‐Amyloid Agents
Marie-Stéphanie Camus (2008)
10.1039/b913845e
Advances in chemical ligation strategies for the synthesis of glycopeptides and glycoproteins.
R. Payne (2010)
10.1021/jo2023125
Long-range intramolecular S → N acyl migration: a study of the formation of native peptide analogues via 13-, 15-, and 16-membered cyclic transition states.
K. Ha (2012)
10.1021/JA00119A001
Unprotected Peptides as Building Blocks for the Synthesis of Peptide Dendrimers with Oxime, Hydrazone, and Thiazolidine Linkages
J. Shao (1995)
10.1039/C39930000369
A reversible protecting group for the amide bond in peptides. Use in the synthesis of ‘difficult sequences’
T. Johnson (1993)
10.1002/(SICI)1097-0282(1999)51:5<311::AID-BIP2>3.0.CO;2-A
Orthogonal ligation strategies for peptide and protein.
J. Tam (1999)
10.1002/CBER.190103402249
Ueber einige Derivate des Glykocolls
E. Fischer (1901)
10.1039/c0lc00542h
Integrated SPPS on continuous-flow radial microfluidic chip.
Weizhi Wang (2011)
10.1002/cmdc.201100405
Synthesis and Functional Characterization of Tridegin and Its Analogues: Inhibitors and Substrates of Factor XIIIa
M. Böhm (2012)
10.1021/bc2002242
Use of model peptide reactions for the characterization of kinetically controlled ligation.
Joon-Goo Lee (2011)
10.1002/anie.201105837
A one-pot three-segment ligation strategy for protein chemical synthesis.
N. Ollivier (2012)
10.1016/0040-4039(91)80673-T
New templates for prior thiol capture from xanthene, dibenzo[c,h]xanthen-7-one and 2-methylenedihydrobenzofuran
D. Kemp (1991)
10.1021/OL0630144
Selective desulfurization of cysteine in the presence of Cys(Acm) in polypeptides obtained by native chemical ligation.
B. Pentelute (2007)
10.1002/ANIE.200600702
Kinetically controlled ligation for the convergent chemical synthesis of proteins.
D. Bang (2006)
10.1038/nature06906
Chemically ubiquitylated histone H2B stimulates hDot1L-mediated intranucleosomal methylation
R. K. McGinty (2008)
10.1016/0040-4039(81)80049-4
Models that demonstrate peptide bond formation by prior thiol capture I. Capture by disulfide formation
D. Kemp (1981)
10.1038/nrd3591
Designing antimicrobial peptides: form follows function
C. Fjell (2012)
10.1039/B612197G
A flow reactor process for the synthesis of peptides utilizing immobilized reagents, scavengers and catch and release protocols.
I. Baxendale (2006)
10.1002/anie.201101920
Total chemical synthesis of a 304 amino acid K48-linked tetraubiquitin protein.
K. Kumar (2011)
10.1002/PSC.928
The depsipeptide technique applied to peptide segment condensation: Scope and limitations
Irene Coin (2008)
10.1002/psc.1383
Chemical synthesis of the third WW domain of TCERG 1 by native chemical ligation
Zerrin Fidan (2011)
10.1021/JA058344I
Insights into the mechanism and catalysis of the native chemical ligation reaction.
E. C. Johnson (2006)
10.1016/S0040-4039(00)96319-6
Peptide synthesis by prior thiol capture…III. Assessment of levels of racemization during two typical thiol capture coupling reactions
B. J. Mcbride (1987)
10.1021/ol202316v
Dual kinetically controlled native chemical ligation using a combination of sulfanylproline and sulfanylethylanilide peptide.
Hao Ding (2011)
10.1021/OL0165239
Atom-Economical Synthesis of the N(10)−C(17) Fragment of Cyclotheonamides via a Novel Passerini Reaction−Deprotection−Acyl Migration Strategy1
Timothy D. Owens and (2001)
10.1021/ja2109079
Chemical synthesis of homogeneous human glycosyl-interferon-β that exhibits potent antitumor activity in vivo.
Izumi Sakamoto (2012)
10.1016/J.TETLET.2007.01.030
Towards the total chemical synthesis of integral membrane proteins: a general method for the synthesis of hydrophobic peptide-thioester building blocks.
E. C. Johnson (2007)
10.1039/c2cc30844d
Oxo-ester mediated native chemical ligation on microarrays: an efficient and chemoselective coupling methodology.
M. Weissenborn (2012)
10.1002/JLAC.19535830110
Über Peptidsynthesen. 8. Mitteilung Bildung von S‐haltigen Peptiden durch intramolekulare Wanderung von Aminoacylresten
T. Wieland (1953)
10.1002/anie.200805225
Plug-based microfluidics with defined surface chemistry to miniaturize and control aggregation of amyloidogenic peptides.
M. Meier (2009)
10.1039/c0cc03666h
Synthesis of histone H3 proteins by a thioacid capture ligation strategy.
X. Zhang (2011)
10.1016/S0968-0896(02)00322-X
New water-soluble prodrugs of HIV protease inhibitors based on O-->N intramolecular acyl migration.
Y. Hamada (2002)
10.1002/anie.200802502
Activation of protein splicing by protease- or light-triggered O to N acyl migration.
M. Vila-Perelló (2008)
10.1002/ANIE.200704195
Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides.
Qian Wan (2007)
10.1002/1097-0282(2001)60:3<194::AID-BIP10031>3.0.CO;2-8
Methods and strategies of peptide ligation.
J. Tam (2001)
10.1002/anie.200801590
Native chemical ligation at valine.
C. Haase (2008)
10.1016/j.bmc.2011.05.018
Application of N-C- or C-N-directed sequential native chemical ligation to the preparation of CXCL14 analogs and their biological evaluation.
Kohei Tsuji (2011)
10.1021/ol300254y
Native chemical ligation at glutamine.
Peter Siman (2012)
10.1039/B408325C
A case study of 2,2-dimethylthiazolidine as locked cis proline amide bond: synthesis, NMR and molecular modeling studies of a delta-conotoxin EVIA peptide analog.
S. Chierici (2004)
10.1016/J.TETLET.2007.01.086
Sequential peptide ligation by using a controlled cysteinyl prolyl ester (CPE) autoactivating unit
T. Kawakami (2007)
10.1002/cbic.201100241
N‐Sulfanylethylanilide Peptide as a Crypto‐Thioester Peptide
K. Sato (2011)
10.1002/cbic.201100179
Ascorbate as an Alternative to Thiol Additives in Native Chemical Ligation
Heike Rohde (2011)
10.1002/anie.200801097
Uncovering a latent ligation site for glycopeptide synthesis.
R. Okamoto (2008)
10.1039/c2cc15911b
Simplifying native chemical ligation with an N-acylsulfonamide linker.
F. Burlina (2012)
10.1002/cbic.201100706
A General Chemical Ligation Approach Towards Isopeptide-Linked Ubiquitin and Ubiquitin-Like Assay Reagents
Paul P. Geurink (2012)
10.1021/JO01351A086
The Kinetics of Alkaline Hydrolysis and n-Butylaminolysis of Ethyl p-Nitrobenzoate and Ethyl p-Nitrothiolbenzoate1a
K. Connors (1961)
10.1021/JA01641A004
The Synthesis of Oxytocin1
V. D. Vigneaud (1954)
10.1002/ANIE.200602167
Microreactor Synthesis of β‐Peptides
Oliver Floegel (2006)
10.1039/c1ob05536d
Alternating chemical ligation reactivity of S-acyl peptides explained with theory and computations.
Alexander A. Oliferenko (2011)
10.1002/ANIE.200353540
A one-pot total synthesis of crambin.
D. Bang (2004)
10.1021/JA060759W
Switch-peptides to trigger the peptide guided assembly of poly(ethylene oxide)-peptide conjugates into tape structures.
J. Hentschel (2006)
10.1002/anie.200803523
Native chemical ligation at valine: a contribution to peptide and glycopeptide synthesis.
J. Chen (2008)
10.1021/JA9836287
Chemical Protein Synthesis by Solid Phase Ligation of Unprotected Peptide Segments
Lynne Canne (1999)
10.1021/ol802268e
Switch peptide via Staudinger reaction.
Natalia Nepomniaschiy (2008)
10.1016/S0040-4020(00)00147-2
Peptide Segment Coupling by Prior Ligation and Proximity-Induced Intramolecular Acyl Transfer
D. M. Coltart (2000)
10.1016/J.TETLET.2008.05.049
Synthesis of cyclic peptides via O–N-acyl migration
Jennifer Lécaillon (2008)
10.1073/PNAS.95.16.9184
Preparation of functionally active cell-permeable peptides by single-step ligation of two peptide modules.
L. Zhang (1998)
10.1039/B304842J
Synthesis of potent β-secretase inhibitors containing a hydroxyethylamine dipeptide isostere and their structure–activity relationship studies
H. Tamamura (2003)
10.1006/ABIO.1996.0011
Thiazolidine formation as a general and site-specific conjugation method for synthetic peptides and proteins.
L. Zhang (1996)
10.1021/JA010726A
Understanding the relative acyl-transfer reactivity of oxoesters and thioesters: computational analysis of transition state delocalization effects.
W. Yang (2001)
10.1073/PNAS.91.14.6584
Peptide segment ligation strategy without use of protecting groups.
C. Liu (1994)
10.1016/j.cbpa.2008.10.009
Expanding the scope of chemoselective peptide ligations in chemical biology.
A. Dirksen (2008)
10.1080/00304940109356592
NEW TRENDS IN PEPTIDE COUPLING REAGENTS
Fernando Albeiicio (2001)
10.1002/cbic.200600112
“Click Peptides”—Chemical Biology‐Oriented Synthesis of Alzheimer's Disease‐Related Amyloid β Peptide (Aβ) Analogues Based on the “O‐Acyl Isopeptide Method”
Y. Sohma (2006)
10.1021/ja2113245
Native chemical ligation of thioamide-containing peptides: development and application to the synthesis of labeled α-synuclein for misfolding studies.
Solongo Batjargal (2012)
10.1016/S0040-4039(02)00755-4
Pseudo-prolines (ΨPro): direct insertion of ΨPro systems into cysteine containing peptides
Jean-François Guichou (2002)
10.2174/138920307782411464
"Forbidden" disulfides: their role as redox switches.
M. A. Wouters (2007)
10.1002/psc.1224
The depsipeptide method for solid‐phase synthesis of difficult peptides
Irene Coin (2010)
10.1021/bc200592c
Atrial natriuretic peptide-Fc, ANP-Fc, fusion proteins: semisynthesis, in vitro activity and pharmacokinetics in rats.
A. Mezo (2012)
10.1002/chem.201103143
A new benzotriazole-mediated stereoflexible gateway to hetero-2,5-diketopiperazines.
Jean-Christophe M. Monbaliu (2012)
10.1002/PSC.634
Synthesis of the C‐terminal region of opioid receptor like 1 in an SDS micelle by the native chemical ligation: effect of thiol additive and SDS concentration on ligation efficiency
T. Sato (2005)
10.1002/ANIE.200463040
Total chemical synthesis and X-ray crystal structure of a protein diastereomer: [D-Gln 35]ubiquitin.
D. Bang (2005)
10.1016/J.TETLET.2011.10.116
Synthesis of an O-acyl isopeptide by using native chemical ligation to efficiently construct a hydrophobic polypeptide
Y. Sohma (2011)
10.1021/JA00897A025
Solid phase peptide synthesis. I. the synthesis of a tetrapeptide
R. Merrifield (1963)
10.1021/jo900853s
Selective synthesis and structural elucidation of S-acyl- and N-acylcysteines.
A. Katritzky (2009)



This paper is referenced by
10.1039/c3cs60384a
Peptidomimetics via modifications of amino acids and peptide bonds.
I. Avan (2014)
10.1021/acs.orglett.6b00292
Visible-Light-Induced Specific Desulfurization of Cysteinyl Peptide and Glycopeptide in Aqueous Solution.
X. Gao (2016)
10.2147/DDDT.S196276
Synthesis, comparative docking, and pharmacological activity of naproxen amino acid derivatives as possible anti-inflammatory and analgesic agents
A. Elhenawy (2019)
10.1039/c3ob40606g
Chemoselective fragment condensation between peptide and peptidomimetic oligomers.
P. Levine (2013)
10.1007/128_2014_594
Postligation-desulfurization: a general approach for chemical protein synthesis.
Jimei Ma (2015)
Development of new bioselective ligation reactions
O. Koniev (2014)
10.1039/c2mb25437a
Synthetic cysteine surrogates used in native chemical ligation.
C. T. Wong (2013)
10.1021/acs.chemrev.5b00443
Recent Developments in General Methodologies for the Synthesis of α-Ketoamides.
C. De Risi (2016)
10.1021/ct300830k
Governing Parameters of Long-Range Intramolecular S-to-N Acyl Transfers within (S)-Acyl Isopeptides.
Jean-Christophe M. Monbaliu (2013)
10.1039/c3ob00030c
Microwave-assisted synthesis of difficult sequence-containing peptides using the isopeptide method.
Waleed M Hussein (2013)
10.1002/psc.3016
Visible‐light photoredox‐catalyzed desulfurization of thiol‐ and disulfide‐containing amino acids and small peptides
Myungmo Lee (2017)
10.1007/978-3-319-31554-6
The Chemistry of Benzotriazole Derivatives: A Tribute to Alan Roy Katritzky
J. Monbaliu (2016)
10.1002/chem.201505135
Continuous-Flow N-Heterocyclic Carbene Generation and Organocatalysis.
Lorenzo Di Marco (2016)
10.1016/j.ijbiomac.2019.12.133
New potential green, bioactive and antimicrobial nanocomposites based on cellulose and amino acid.
M. Hasanin (2019)
10.1021/ol502773v
Postsynthetic modification of unprotected peptides via S-tritylation reaction.
Masayoshi Mochizuki (2014)
10.1039/c5cs00048c
Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation.
O. Koniev (2015)
10.1007/s13361-015-1319-3
S- to N-Palmitoyl Transfer During Proteomic Sample Preparation
Yuhuan Ji (2016)
10.1021/jacs.7b05850
Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine.
Guillaume De Bo (2017)
10.1021/ar400242q
Traceless chemical ligation from S-, O-, and N-acyl isopeptides.
S. Panda (2014)
10.1007/7081_2015_198
Benzotriazole: Much More Than Just Synthetic Heterocyclic Chemistry
Kiran Bajaj (2015)
10.1016/j.bmcl.2015.05.020
Synthesis, molecular docking and anticancer studies of peptides and iso-peptides.
Farukh Jabeen (2015)
10.3389/fchem.2014.00028
Realizing serine/threonine ligation: scope and limitations and mechanistic implication thereof
C. T. Wong (2014)
10.1021/ACS.CHEMREV.6B00237
Nonclassical Routes for Amide Bond Formation.
R. M. de Figueiredo (2016)
10.1002/ADSC.201700765
Palladium‐Catalyzed Isocyanide Insertion with Allylic Esters: Synthesis of N‐(But‐2‐enoyl)‐N‐(tert‐butyl)benzamide Derivatives via Intramolecular Acyl Transfer Termination
Si Chen (2017)
10.1007/128_2014_608
Applications of Chemical Ligation in Peptide Synthesis via Acyl Transfer.
Siva S Panda (2015)
10.3390/molecules23040761
Synthesis, Molecular Docking Studies, In Vitro Antimicrobial and Antifungal Activities of Novel Dipeptide Derivatives Based on N-(2-(2-Hydrazinyl-2-oxoethylamino)-2-oxoethyl)-Nicotinamide
G. Moustafa (2018)
10.1002/chem.201400125
Long-range chemical ligation from N→N acyl migrations in tryptophan peptides via cyclic transition states of 10- to 18-members.
Suvendu Biswas (2014)
10.1002/CHIN.201310230
Recent Trends in Cys‐ and Ser/Thr‐Based Synthetic Strategies for the Elaboration of Peptide Constructs
J. Monbaliu (2013)
10.1039/c5cc04846j
Total chemical synthesis of the site-selective azide-labeled [I66A]HIV-1 protease.
Y. Qi (2015)
10.1039/c3ob41027g
Synthesis of human growth hormone-releasing hormone via three-fragment serine/threonine ligation (STL).
Y. Zhang (2013)
10.1007/7081_2015_199
Acylbenzotriazoles: New Allies for Short Linear and Cyclic Peptide Constructs
Danniebelle N. Haase (2016)
Title Realizing serine / threonine ligation : scope and limitations andmechanistic implication thereof
Clarence Tsun Ting Wong (2014)
See more
Semantic Scholar Logo Some data provided by SemanticScholar