TRYPTOPHAN-NORLEUCINE 1,5-DISUBSTITUTED TETRAZOLES AS CIS PEPTIDE-BOND MIMICS - INVESTIGATION OF THE BIOACTIVE CONFORMATION OF A POTENT ANDSELECTIVE PEPTIDE FOR THE CHOLECYSTOKININ-B RECEPTOR

Authors
BOTEJU LW ZALEWSKA T YAMAMURA HI HRUBY VJ
Citation
Lw. Boteju et al., TRYPTOPHAN-NORLEUCINE 1,5-DISUBSTITUTED TETRAZOLES AS CIS PEPTIDE-BOND MIMICS - INVESTIGATION OF THE BIOACTIVE CONFORMATION OF A POTENT ANDSELECTIVE PEPTIDE FOR THE CHOLECYSTOKININ-B RECEPTOR, Bioorganic & medicinal chemistry letters, 3(10), 1993, pp. 2011-2016
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
10
Year of publication
1993
Pages
2011 - 2016
Database
ISI
SICI code
0960-894X(1993)3:10<2011:T1TACP>2.0.ZU;2-#
Abstract
It has been suggested that the cis conformation about the Trp-N-MeNle amide bond is important in conferring high affinity and selectivity to CCK-B receptor ligands. Substitution of the cis amide bond mimic Trp psi(CN4)Nle into the peptide Gly-Trp-N-(Me)Nle-Asp-PheNH(2) causes it to lose activity, suggesting that other structural effects of N-(Me)Nl e incorporation may be important for high affinity and selectivity for the CCK-B receptor.