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

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.