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Synthesis Of Hybrid Peptidomimetics And Neoglycoconjugates Employing Click Protocol: Dual Utility Of Poc-Group For Inserting Carbamate-Triazole Units Into Peptide Backbone

H. Hemantha, Ravi S. Lamani, Vommina V. Sureshbabu
Published 2010 · Chemistry

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Synthesis of new types of peptidomimetics and glycosylated amino acids possessing 1,2,3-triazole and carbamate moieties is described. Poc-protected amino acid esters/1-amino sugars were subjected to Cu(I) catalyzed [2+3]cycloaddition with desired azides under click protocol to obtain novel peptide and carbohydrate mimetics. The reaction is rapid, efficient and all the products are isolated in good yield and excellent purity.
This paper references
10.1021/jm060754
Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization.
Matthew Whiting (2006)
10.1002/BIP.360370305
Novel biopolymers for drug discovery
E. Moran (1995)
10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
V. Rostovtsev (2002)
10.1002/9783527626038
Peptides: Chemistry and Biology
N. Sewald (2002)
10.1002/ANIE.200502161
Inhibitors of HIV-1 protease by using in situ click chemistry.
Matthew Whiting (2006)
10.1039/B618048P
Recent applications of the Cu(I)-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry.
Simone Dedola (2007)
10.1021/JO0611723
Preparation, Isolation, and Characterization of Nα-Fmoc-peptide Isocyanates: Solution Synthesis of Oligo-α-peptidyl Ureas
V. V. Sureshbabu (2006)
Padwa A (ed) 1,3-Dipolar cycloaddition chemistry
R Huisgen (1984)
10.1055/S-2007-966071
Click Chemistry - What’s in a Name? Triazole Synthesis and Beyond
M. V. Gil (2007)
10.1021/JA0318636
Chiral lewis Acid catalysis in nitrile oxide cycloadditions.
M. P. Sibi (2004)
10.1002/CHIN.200135279
Click Chemistry: Diverse Chemical Function from a Few Good Reactions
H. Kolb (2001)
10.1016/J.TETLET.2009.09.172
A simple approach for the synthesis of new classes of dithiocarbamate-linked peptidomimetics
H. Hemantha (2009)
10.1021/BM070430I
Efficient synthesis of linear multifunctional poly(ethylene glycol) by copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition.
X. Liu (2007)
10.1002/cbic.200500101
1,2,3‐Triazole as a Peptide Surrogate in the Rapid Synthesis of HIV‐1 Protease Inhibitors
A. Brik (2005)
10.1021/jo900675s
N-urethane-protected amino alkyl isothiocyanates: synthesis, isolation, characterization, and application to the synthesis of thioureidopeptides.
V. Sureshbabu (2009)
10.1002/1521-3765(20010401)7:7<1371::AID-CHEM1371>3.0.CO;2-J
Chemical synthesis of linear and cyclic unnatural oligosaccharides by iterative glycosidation of ketoses.
A. Dondoni (2001)
10.1002/JHET.5570270338
Synthesis of 1-aryl-1,2,3-triazole-4,5-dimethanol-4,5-bis(isopropylcarbamates) as potential antineoplastic agents †
I. Lalezari (1990)
10.1002/CHIN.200636184
Simultaneous Protection and Activation of Amino Acids Using Propargyl Pentafluorophenyl Carbonate.
R. Ramesh (2006)
10.1021/JM060754+
Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization.
M. Whiting (2006)
10.1021/JA034358H
A heterocyclic peptide nanotube.
W. Horne (2003)
Pseudo-peptides in drug discovery : A newer technology
T. Patel (2010)
10.1002/psc.1187
One‐pot protection and activation of amino acids using pentafluorophenyl carbonates
Ramesh Ramapanicker (2009)
10.1016/j.bmc.2009.10.003
Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity.
Subhra Prakash Chakrabarty (2009)
10.1021/JA963895H
HIV-1 TAR RNA Recognition by an Unnatural Biopolymer
X. Wang (1997)
10.1055/S-0029-1219393
Synthesis of thioureido-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates using bis(benzotriazolyl)methanethione as thioacylating agent
V. Sureshbabu (2010)
10.1021/JO011148J
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
C. W. Tornøe (2002)
10.1002/CHIN.200903259
β‐Peptidic Peptidomimetics
D. Seebach (2009)
10.1007/s10989-007-9101-4
A Facile Synthesis of C-terminal Neoglycopeptides: Incorporation of Urea Moiety between Sugars and Peptides Employing Curtius Rearrangement
Vommina V. Sureshbabu (2007)
10.1002/CHIN.200439167
Highly Efficient Enantiospecific Synthesis of Imidazoline-Containing Amino Acids Using Bis(triphenyl)oxodiphosphonium Trifluoromethanesulfonate.
S. You (2004)
10.1002/CHIN.199830310
Foldamers: A Manifesto
Samuel H. Gellman (1998)
10.1021/ja0450408.s001
Heterocyclic peptide backbone modifications in an alpha-helical coiled coil.
W. Horne (2004)
10.1016/j.bmcl.2008.06.020
Natural products in parallel synthesis: triazole libraries of nonactic acid.
Sarah B. Luesse (2008)
10.1021/jo902249w
From peptides to their alternating ester-urea analogues: synthesis and influence of hydrogen bonding motif and stereochemistry on aggregation.
Sebastian Hartwig (2010)
10.1002/CHIN.200318180
Propargyloxycarbonyl (Poc) as a Protective Group for the Hydroxyl Function in Carbohydrate Synthesis.
P. R. Sridhar (2003)
10.1021/JA056406Z
Nonpeptidic foldamers from amino acids: synthesis and characterization of 1,3-substituted triazole oligomers.
Nicholas G. Angelo (2005)
10.1039/B109128J
α-Methylene tetrazole-based peptidomimetics: synthesis and inhibition of HIV protease
B. C. May (2002)
10.1021/JO060374W
Sonochemistry: a powerful way of enhancing the efficiency of carbohydrate synthesis.
S. Deng (2006)
10.1021/CC020085V
Combinatorial library of peptidotriazoles: identification of [1,2,3]-triazole inhibitors against a recombinant Leishmania mexicana cysteine protease.
C. W. Tornøe (2004)
10.1039/CC9960001957
Prop-2-ynyl as a protective group for carboxylic acids: a mild method for the highly selective deprotection of prop-2-ynyl esters using tetrathiomolybdate
P. Ilankumaran (1996)
10.1016/j.cbpa.2008.03.009
Peptidomimetics, a synthetic tool of drug discovery.
J. Vágner (2008)
10.1039/B616751A
1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics.
Victoria D. Bock (2007)
10.1021/JA043031T
In situ selection of lead compounds by click chemistry: target-guided optimization of acetylcholinesterase inhibitors.
A. Krasiński (2005)
10.1016/J.CARRES.2006.04.028
Synthesis of multivalent lactose derivatives by 1,3-dipolar cycloadditions: selective galectin-1 inhibition.
Johan Tejler (2006)
10.1021/OL005777B
Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor.
A. J. Phillips (2000)
10.1021/ar700263g
Beta-peptidic peptidomimetics.
D. Seebach (2008)
10.1021/JA9734399
Synthesis and Screening of Linear and Cyclic Oligocarbamate Libraries. Discovery of High Affinity Ligands for GPIIb/IIIa
C. Y. Cho (1998)
10.1002/ANIE.196306331
Kinetics and Mechanism of 1,3‐Dipolar Cycloadditions
R. Huisgen (1963)
10.1002/ANIE.199615031
Synthesis of Naturally Occurring, Conformationally Restricted Oxazole‐ and Thiazole‐Containing Di‐ and Tripeptide Mimetics
G. Videnov (1996)
10.1016/J.TETLET.2008.06.091
Synthesis of 1,2,4-oxadiazole-linked orthogonally urethane-protected dipeptide mimetics
V. Sureshbabu (2008)
10.1021/OL051960Z
But-2-ynylbisoxycarbonyl chloride: a novel C2-symmetric reagent for the protection of amines and amino acids.
R. Ramesh (2005)
10.1002/ANIE.196305651
1,3-Dipolar Cycloadditions. Past and Future†
R. Huisgen (1963)
10.1126/SCIENCE.7689747
An unnatural biopolymer.
C. Y. Cho (1993)
10.1021/OL053095O
Click chemistry as a route to cyclic tetrapeptide analogues: synthesis of cyclo-[Pro-Val-psi(triazole)-Pro-Tyr].
Victoria D. Bock (2006)
10.1021/jo0516180.s001
Ring closure to beta-turn mimics via copper-catalyzed azide/alkyne cycloadditions.
Yu Angell (2005)
10.1016/S1359-6446(03)02933-7
The growing impact of click chemistry on drug discovery.
H. Kolb (2003)
10.1016/S0040-4039(02)00287-3
Synthesis and applications of propargyl pentafluorophenyl carbonate for peptide synthesis
R. Bhat (2002)
10.1016/J.TET.2006.06.001
Synthetic utility of glycosyl triazoles in carbohydrate chemistry
Brendan L Wilkinson (2006)
10.1021/OL048841O
Expedient synthesis of triazole-linked glycosyl amino acids and peptides.
Brian H. M. Kuijpers (2004)
10.1055/B-003-111718
Synthesis of Peptides and Peptidomimetics
M. Goodman (2003)



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