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Regioselective anodic oxidation of N ‐acyl, N ‐alkoxycarbonyl, and N ‐(2‐Nitrophenylsulfenyl) dipeptide esters
Author(s) -
Papadopoulos Apostolos,
Heyer Joachim,
Ginzel KlausDieter,
Steckhan Eberhard
Publication year - 1989
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19891221117
Subject(s) - chemistry , regioselectivity , dipeptide , electrolysis , amino acid , anodic oxidation , moiety , chloride , medicinal chemistry , stereochemistry , organic chemistry , anode , catalysis , biochemistry , electrode , electrolyte
The chloride‐mediated anodic methoxylation of protected dipeptide esters shows high regioselectivity. It is influenced by the N ‐protecting groups and the amino acid side‐chains. The anodic methoxylation may be effectively directed to the selective oxidation of the C‐terminal amino acid. Regioselective oxidation of the N‐terminal amino acid is obtained by direct electrolysis of N ‐(2‐nitrophenylsulfenyl)‐protected dipeptides with formation of the sulfenimino dipeptides.