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Conformational Consequences of Regio‐ and Stereoselective Disulfide Bridge Oxidation in a Cyclic Peptide
Author(s) -
Malešević Miroslav,
Jahreis Günther,
Wawra Stephan,
Fischer Gunter,
Lücke Christian
Publication year - 2008
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200700529
Subject(s) - moiety , stereoselectivity , disulfide bond , chemistry , peptide , cyclic peptide , sulfur , stereochemistry , nuclear magnetic resonance spectroscopy , combinatorial chemistry , organic chemistry , catalysis , biochemistry
Synthesis of thiosulfinates . A thiosulfinate moiety was introduced into a cyclic peptide by regio‐ and stereoselective disulfide‐bridge oxidation of S 2 , S 6 ‐cyclo(H‐Gly‐Cys‐Ser‐Pro‐Ala‐Cys‐Gly‐OH). The CD, FTIR and NMR spectroscopic data demonstrated drastic changes in the peptide secondary structure upon oxidation of the Cys6 sulfur atom, while oxidation of the Cys2 sulfur atom caused only minor structure perturbations.