Strained-Cyclophane-Induced beta -Turn Template: Design, Synthesis, and Spectroscopic Characterization
2004
Abstract
Three tetrapeptides incorporating a 14-membered (Ri+1, Si+2) cycloisodityrosine at the i + 1 and i + 2 positions were designed and synthesized. Conformational anal. by 1H NMR and CD spectra as well as mol. modeling indicated that they all adopt a beta -turn conformation. While the CD spectrum of peptide I is characteristic of the typical type-II beta -turn (max. at .apprx.200 nm and a min. at .apprx.220 nm), that of peptide II (atropisomer of I) is opposite in sign to the expected spectrum of the type-II beta -turn. [on SciFinder (R)]
Details
Title
Strained-Cyclophane-Induced beta -Turn Template: Design, Synthesis, and Spectroscopic Characterization
Author(s)
Cristau, Pierre ; Martin, Marie-Therese ; Dau, Marie-Elise Tran Huu ; Vors, Jean-Pierre ; Zhu, Jieping
Published in
Organic Letters
Volume
6
Issue
18
Pages
3183-3186
Date
2004
ISSN
1523-7060
Keywords
Atropisomers; Conformation; beta -Turn (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); Cyclophanes Role: PRP (Properties); SPN (Synthetic preparation); PREP (Preparation) (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); Peptides Role: PRP (Properties); SPN (Synthetic preparation); PREP (Preparation) (tetrapeptides; prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); beta -Turn (type II; prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); cycloisodityrosine tetrapeptide strained cyclophane beta turn prepn conformation
Note
CAN 141:314608
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
765949-94-8P; 765949-97-1P; 765950-28-5P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); 616-34-2 (Methyl glycinate); 13139-15-6; 16937-99-8; 203311-03-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); 765950-29-6P; 765950-38-7P; 765950-39-8P; 765950-40-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates)
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
765949-94-8P; 765949-97-1P; 765950-28-5P Role: PRP (Properties), SPN (Synthetic preparation), PREP (Preparation) (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); 616-34-2 (Methyl glycinate); 13139-15-6; 16937-99-8; 203311-03-9 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates); 765950-29-6P; 765950-38-7P; 765950-39-8P; 765950-40-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and conformation anal. of cycloisodityrosine-based tetrapeptides as strained cyclophane-induced beta -turn templates)
Laboratories
LSPN
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2010-11-25