Premium
Derivatives of 3,4‐dihydro‐β‐carboline‐3‐carboxylic acid from c‐terminal tryptophan‐containing peptides. Synthesis and properties
Author(s) -
Letellier Sabine,
Fleury Bernard,
Torreilles Jean,
Previero Aldo
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250444
Subject(s) - chemistry , tryptophan , isomerization , carbanion , carboxylic acid , yield (engineering) , fluorescence , amino acid , combinatorial chemistry , organic chemistry , stereochemistry , catalysis , biochemistry , materials science , physics , quantum mechanics , metallurgy
C ‐Terminal tryptophan containing peptides have been converted into 1‐peptidyl‐3,4‐dihydro‐β‐carboline‐3‐carboxylic acids by acid catalyzed isomerization of their azlactone derivatives. The main properties of these abnormal peptides are a strong absorption around 360 nm an intense yellow fluorescence and ability to generate reactive carbanions when dissolved in basic media. This tryptophan conversion takes place with high yield and is of general applicability.