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

The Photochemistry Of N-p-Toluenesulfonyl Peptides: The Peptide Bond As An Electron Donor

R. R. Hill, S. Moore, D. Roberts
Published 2005 · Chemistry, Medicine

Save to my Library
Download PDF
Analyze on Scholarcy
Share
Abstract The scope of photobiological processes that involve absorbers within a protein matrix may be limited by the vulnerability of the peptide group to attack by highly reactive redox centers consequent upon electronic excitation. We have explored the nature of this vulnerability by undertaking comprehensive product analyses of aqueous photolysates of 12 N-p-toluenesulfonyl peptides with systematically selected structures. The results indicate that degradation includes a major pathway that is initiated by intramolecular electron transfer in which the peptide bond serves as electron donor, and the data support the likelihood of a relay process in dipeptide derivatives.
This paper references
10.1021/JO00250A030
.pi.-Acceptor-induced reactions. Unusual selectivity in bond-cleavage reactions through the use of photochemical excitation
J. Penn (1988)
10.1021/JP991123C
Femtosecond Photoionization of Ion Beam Desorbed Aliphatic and Aromatic Amino Acids: Fragmentation via α-Cleavage Reactions
V. Vorsa (1999)
10.5860/choice.34-3868
Protein Electron Transfer
D. Bendall (1997)
10.1021/JP010603C
Efficiency of Charge Transport in a Polypeptide Chain: The Hydrated System †
S. Sheu (2001)
10.1002/CHIN.198736091
Reductive Cleavage of Sulfonates. Deprotection of Carbohydrate Tosylates by Photoinduced Electron Transfer.
J. Masnovi (1987)
Studies in light absorption, Part 11: 2,4-DNPs
E. A. Braude (1945)
Racemization of tripeptides and hydantoins
M. Bovamick (1938)
10.1007/BF00844231
The preparation of peptides
V. A. Nekrasova (1964)
10.1021/JA01569A071
Tosyl-α-amino Acids. I. Degradation of the Acid Chlorides and Azides by Aqueous Alkali
A. Beecham (1957)
Photosystem II: molecular structure and function—introduction
J. Barber (2002)
Krasil'nikov, I1 and 0. V. Arapov (1997) Synthesis and radiation-protective properties of dipeptide 103,572-581. derivatives of S-(2-aminoethyl)phosphothioates and S-butyryl-2-aminoethanethiol
M Y Malov
Scheme 10. Possible mechanism for relayed IET in the photolysis of N-p- tosylglycylglycine
10.1021/JA036733B
Free radical reactions of methionine in peptides: mechanisms relevant to beta-amyloid oxidation and Alzheimer's disease.
C. Schöneich (2003)
10.1016/S0040-4020(98)01029-1
Synthetic and photochemical studies of N-arenesulfonyl amino acids
G. Papageorgiou (1999)
10.1039/A905358A
Photodegradation of aryl sulfonamides: N-tosylglycine
R. R. Hill (1999)
10.1038/142653a0
Practical Organic Chemistry
J. T. (1938)
Synthesis and radiation-protective properties of dipeptide Scheme 10. Possible mechanism for relayed IET in the photolysis of N-p- tosylglycylglycine
M. Y. Malov (1997)
10.1021/ic50133a004
Ligand oxidation in iron diimine complexes. I. Stoichiometry and products of the oxidation of tris(glyoxal bis(methylimine))iron(II) by cerium(IV)
H. L. Chum (1974)
10.1002/CHIN.198917110
A Comprehensive Photochemical and Photophysical Assay Exploring the Photoreactivity of Drugs.
T. Oppenlaender (1989)
10.1021/JA00385A029
Chiral and stereochemical control via intramolecular Diels-Alder reaction of Z dienes
S. Pyne (1982)
10.1021/JA01174A062
2-Azetidinone (β-Propiolactam)
R. Holley (1949)
Soumillion (1999) Communi- cation between surfaces by electron relay in a doubly heterogeneous photochemical reaction
M. Ayadim (1999)
Nishida and 0. Yonemitsu (1979) Mechanism of photodetosylation of N-tosyl-1,2,3,4-tetrahydroisoquinoEnes involving electron transfer in the excited state
T Hamada
10.5860/choice.31-6053
Fundamentals of Photoinduced Electron Transfer
G. Kavarnos (1993)
10.1071/CH9700413
Reactions of methylamine and aniline with methyl pyruvate
P. Pojer (1970)
10.1021/JA01569A072
Tosyl-α-amino Acids. II. The Use of the Acid Chlorides for Peptide Synthesis in the Presence of Aqueous Alkali
A. Beecham (1957)
Holley (1949) 2-Azetidinone (b-propiolactam )
R W Holley
Photosystem 11: the engine of life
J. Barber (2003)
2-Azetidinone (b-propiolac- tam).J
R. W. Holley (1949)
10.1039/JR9600001662
334. Alternaric acid. Part III. Structure
J. R. Bartels-Keith (1960)
Practical Organic Chemistry
F. G. Mann (1965)
10.1002/CHIN.197614115
SYNTHESIS OF TERTIARY AMINES BY SELECTIVE DIBORANE REDUCTION
Pamela A. Russ (1976)
Alternaric acid, Part 111: structure
J. R. Bartels-Keith (1960)
The isomeric dipeptides of valiie including a correction
J. W. Hinman (1950)
10.1562/RC-122R.1
Redox Photochemistry of Thiouredopyrenetrisulfonate¶
A. Kotlyar (2004)
10.1021/JA01160A053
The Isomeric Dipeptides of Valine Including a Correction1
J. Hinman (1950)
Free radical reactions of methionine in peptides: mechanisms relevant to bamyloid oxidation and Alzheimer's disease
C Schoneich (2003)
Techniques of Electroorganic Chemistry Part 2Edited by N. L. Weinberg), Appendix
H Siegerman (1975)
10.1016/S0005-2728(00)00213-9
Photosynthetic water oxidation.
J. Nugent (2001)
10.1021/JP9832802
Intramolecular electron transfer across amino acid spacers in the picosecond time regime. Charge-transfer interaction through peptide bonds
Guilford Jones (1999)
10.1021/JA994150P
Ei Elimination: An Unprecedented Facet of Sulfone Chemistry
J. Cubbage (2000)
10.1039/J39670002371
Amino-acids and peptides. XXVI. The use of 1-piperidyl esters in peptide synthesis: further studies.
J. H. Jones (1967)
10.1039/P29960001595
Photo-induced electron transfer in small peptides: glycylalanine
R. R. Hill (1996)
Free radical reactions of methionine in peptides: mechanisms relevant to pamyloid oxidation and Alzheimer’s disease
C. Schoneich (2003)
10.1021/JP045797L
Understanding electron transfer across negatively-charged Aib oligopeptides.
R. Improta (2005)
10.1039/JR9450000498
128. Studies in light absorption. Part II. 2 : 4-Dinitrophenylhydrazones
E. A. Braude (1945)
10.1002/CHIN.200526232
Photoremovable Protecting Groups Based on Electron Transfer Chemistry
D. Falvey (2005)
10.1021/JA0401040
Long-range electron transfer across Peptide bridges: the transition from electron superexchange to hopping.
Rouba Abdel Malak (2004)
10.1002/CHIN.199640093
Synthesis and Evaluation of Photolabile Sulfonamides as Potential Reagents for Rapid Photorelease of Neuroactive Amines.
J. Corrie (1996)
10.1021/JP047900C
Electron transfer through H-bonded peptide assemblies
Heinz-Bernhard Kraatz (2004)
10.1039/B308525B
Competitive electron transfers from a tyrosyl side-chain and peptide bond in the photodegradation of N-tosyl alpha-aminomethylamides: an insight into photosynthesis and photodamage in the biological oxidation of water?
R. R. Hill (2003)
10.1021/JA0467059
Oxidation of methionine residues in aqueous solutions: free methionine and methionine in granulocyte colony-stimulating factor.
Jhih-Wei Chu (2004)
10.1039/C39860000293
Photoinduced electron transfer in aliphatic peptides
D. Birch (1986)
10.3109/15569529709048889
In Vitro Phototoxicity Due to Sulfonamide-Derived Oral Antidiabetic and Diuretic Drugs
E. Selvaag (1997)
Synthesis and radiation-protective properties of dipeptide derivatives of S-(2-aminoethyl) phosphothioates and S-butyryl-2-aminoethanethiol
M. Malov (1997)
New approaches to the asymmetric-synthesis of non-proteinogenic a-amino-acids and dipep859-870. tides through chiral p-lactam intermediates
I. Ojima (1988)
10.1002/ANIE.198006481
Photochemistry of sulfonamides and sulfonylureas: a contribution to the problem of light-induced dermatoses.
B. Weiss (1980)
Synthesis of peptides containing a-hydroxy-a-amino acid residues
M. M. Shemyakin (1956)
Bietti and 0. Lanzalunga (2000) Mechanistic aspects of P-bond-cleavage reactions of aromatic radical cations
E Baciocchi
10.1002/CHIN.199012069
A New Amino Protecting Group Readily Removable with Near Ultraviolet Light as an Application of Electron-Transfer Photochemistry.
T. Hamada (1990)
10.1002/CHIN.197940218
MECHANISM OF PHOTODETOSYLATION OF N-TOSYL-1,2,3,4-TETRAHYDROISOQUINOLINES INVOLVING ELECTRON TRANSFER IN THE EXCITED STATE
O. Yonemitsu (1979)
Drugs, photochemistry and photostability
A. Albini (1998)
10.1021/JA043607E
Evidence against the hopping mechanism as an important electron transfer pathway for conformationally constrained oligopeptides.
F. Polo (2005)
10.1021/JO50011A022
Some Derivatives of the Stereoisomeric β-Phenylserines. Conversion of the Threo to the Erythro Form
W. Fones (1952)
Intramolecular electron transfer across amino acid spacers in the picosecond time regime : charge - transfer interaction through peptide bands
A. B. Kotlyar (1999)
10.1007/0-306-48135-9
Photosynthesis and the Environment
N. Baker (1996)
Possible mechanism for relayed IET in the photolysis of N-ptosylglycylglycine
Photosystem 11: molecular structure and function-introduction
J. Barber (2002)
10.1016/S0040-4020(01)86038-5
New approaches to the asymmetric synthesis of non-proteinogenic α-amino acids and dipeptides through chiral β-lactam intermediates
I. Ojima (1988)
10.1021/JA030659F
Evidence for through-space electron transfer in the distance dependence of normal and inverted electron transfer in oligoproline arrays.
S. Serron (2004)
10.1021/JA954077C
Rates of Uncatalyzed Peptide Bond Hydrolysis in Neutral Solution and the Transition State Affinities of Proteases
A. Radzicka (1996)
10.3184/030823403103174759
Photochromic Behaviour of N-Arylsulfonyl Peptides †
R. R. Hill (2003)
10.1021/JA01285A046
The Identification of the Amino Acids: p-Toluenesulfonyl1 Chloride as a Reagent
E. McChesney (1937)
10.1016/S0040-4020(97)90399-9
Reduction of 2-acylaziridines by samarium(II) iodide. An efficient and regioselective route to β-amino carbonyl compounds
G. Molander (1997)
10.1002/PRAC.19873290514
Photochemie von Aminoketonen. X. Darstellung und diastereoselektive Photocyclisierung von N‐(β‐Benzoylethyl)‐N‐tosyl‐glycinamiden
K. Walther (1987)
10.1021/JA00005A053
Photochemistry of dipeptides in aqueous solution
R. R. Hill (1991)
10.1021/JP037779U
Photooxidation of glycylglycine. Two-channel reaction mechanism as studied by time-resolved FT EPR
Peter Tarábek (2004)
10.1017/S0033583502003839
Photosystem II: the engine of life.
J. Barber (2003)
10.1021/JA990316A
Communication between surfaces by electron relay in a doubly heterogeneous photochemical reaction
M. Ayadim (1999)
10.1021/AR980014Y
Mechanistic Aspects of β-Bond-Cleavage Reactions of Aromatic Radical Cations
E. Baciocchi (2000)
Intramolecular electron transfer across amino acid spacers in the picosecond time regime : charge - transfer interaction through peptide bands
G. Jones (1999)
10.1515/BCHM2.1926.154.4-6.203
Ein Beitrag zur Bereitung von Peptiden.
R. Schoenheimer (1926)
Photochemistry of aminoketones, 10: preparation and diastereoselective photocyclization of N-(b-benzoylethyl)-N-tosyl-glycinamides
K. Walther (1987)
10.1016/0003-2670(56)80113-X
Practical organic chemistry, including qualitative organic analysis
N. Strafford (1956)
10.1021/JA029787E
Anomalous distance dependence of electron transfer across peptide bridges.
S. Antonello (2003)
10.1021/JA01277A036
Racemization of Tripeptides and Hydantoins1
M. Bovarnick (1938)
10.1007/0-306-48135-9_4
Mechanisms of Photodamage and Protein Degradation During Photoinhibition of Photosystem II
B. Andersson (1996)
Photochemistry of aminoketones, 10: preparation and diastereoselective photocyclization of N-(P-benzoylethy1)-N-tosyl-glycinamides
K. Walther (1987)
10.1002/chin.198619132
Selective Removal of Electron-Accepting p-Toluene- and Naphthalenesulfonyl Protecting Groups for Amino Function via Photoinduced Donor - Acceptor Ion Pairs with Electron-Donating Aromatics.
T. Hamada (1986)
10.1201/9780367801021
Photostability of Drugs and Drug Formulations
H. Tønnesen (2004)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar