PROTECTION OF THE PEPTIDE-BOND AGAINST ALPHA-CHYMOTRYPSIN BY THE PRODRUG APPROACH

Authors
KAHNS AH FRIIS GJ BUNDGAARD H
Citation
Ah. Kahns et al., PROTECTION OF THE PEPTIDE-BOND AGAINST ALPHA-CHYMOTRYPSIN BY THE PRODRUG APPROACH, Bioorganic & medicinal chemistry letters, 3(5), 1993, pp. 809-812
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
5
Year of publication
1993
Pages
809 - 812
Database
ISI
SICI code
0960-894X(1993)3:5<809:POTPAA>2.0.ZU;2-1
Abstract
N-Hydroxymethylation of the N-terminal peptide bond in N-acetyl-L-phen ylalanine amides was found to protect the C-terminal amide bond agains t cleavage by alpha-chymotrypsin. The N-hydroxymethyl derivatives are readily bioreversible, undergoing spontaneous hydrolysis at physiologi cal pH, and are thus promising prodrugs to overcome the enzymatic barr ier to absorption of various peptides.