Epimerization during coupling to the unnatural amino acid in solid phase peptide synthesis

Authors
Zhang, ZY Van Aerschot, A Chaltin, P Busson, R Herdewijn, P
Citation
Zy. Zhang et al., Epimerization during coupling to the unnatural amino acid in solid phase peptide synthesis, COLL CZECH, 66(6), 2001, pp. 923-932
Citations number
12
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry
Journal title
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS
ISSN journal
0010-0765 → ACNP
Volume
66
Issue
6
Year of publication
2001
Pages
923 - 932
Database
ISI
SICI code
0010-0765(200106)66:6<923:EDCTTU>2.0.ZU;2-P
Abstract
Extensive epimerization was observed during the coupling of FmOC-L-Trp(Boc) and FmoC-L-Pro to D-Ual, a synthetic a-amino acid with a nucleobase in the side chain. This unnatural amino acid was used extensively in the construc tion of nucleic acids recognition libraries. Reaction protocols based on th e use of DIC-HOAt-DIEA mixture without preactivation of the coupling mixtur e has been proven to suppress the epimerization reaction significantly.