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Synthesis of ψ[SCH 2 ]‐, ψ[SOCH 2 ]‐, and ψ[SO 2 CH 2 ]‐Peptide Isosters
Author(s) -
Sommerfeld Thimo,
Seebach Dieter
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199505531
Subject(s) - peptide , chemistry , sulfur , oxidation state , amino acid , electrolysis , nitrogen atom , nitrogen , stereochemistry , combinatorial chemistry , catalysis , organic chemistry , electrode , biochemistry , ring (chemistry) , electrolyte
Novel peptide analogues 2 containing ‐SO n ‐CH 2 ‐ instead of ‐CO‐NH‐ ( n = 0, 1, 2) may be prepared as single stereoisomers from amino acids and peptides 1 by electrolysis, reaction with 3‐mercaptocarboxylic acids, and oxidation. The stability of 2 (especially under basic conditions) decreases with increasing oxidation state at sulfur and with increasing donor ability of the nitrogen atom.