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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Kerwin, Bruce A. Schöneich, Christian Mozziconacci, Olivier |
| Description | Author Affiliation: Mozziconacci O ( Department of Pharmaceutical Chemistry, 2095 Constant Avenue, University of Kansas, Lawrence, Kansas 66047, United States.) |
| Abstract | The photodissociation of disulfide bonds in model peptides containing Ala and Ala-d(3) generates a series of photoproducts following the generation of a CysS(â ¢) thiyl radical pair. These photoproducts include transformations of Cys to dehydroalanine (Dha) and Ala, as well as Ala to Dha. Intramolecular Michael addition of an intact Cys with a photolytically generated Dha results in the formation of cyclic thioethers. The conversion of Cys into Dha likely involves a 1,3-H-shift from the Cys ( )C-H bond to the thiyl radical, followed by elimination of HS(â ¢). The conversion of Dha into Ala most likely involves hydrated electrons, which are generated through the photolysis of Cys, the photoproduct of disulfide photolysis. Prior to stable product formation, CysS(â ¢) radicals engage in reversible hydrogen transfer reactions with ( )C-H and (ß)C-H bonds of the surrounding amino acids. Especially for the (ß)C-H bonds of Ala, such hydrogen transfer reactions are unexpected on the basis of thermodynamic grounds; however, the replacement of deuterons in Ala-d(3) by hydrogens in H(2)O provides strong experimental evidence for such reactions. |
| ISSN | 15206106 |
| e-ISSN | 15205207 |
| Journal | The Journal of Physical Chemistry B |
| Issue Number | 42 |
| Volume Number | 115 |
| Language | English |
| Publisher | American Chemical Society (United States) |
| Publisher Date | 2011-10-27 |
| Publisher Place | United States |
| Access Restriction | Open |
| Subject Keyword | Alanine Analogs & Derivatives Chemistry Cysteine Free Radicals Hydrogen Peptides Amino Acid Sequence Deuterium Exchange Measurement Deuterium Oxide Hydrogen-Ion Concentration Photolysis Thermodynamics Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't Physical chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Surfaces, Coatings and Films Materials Chemistry Medicine Physical and Theoretical Chemistry |
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