Strained-Cyclophane-Induced beta -Turn Template: Design, Synthesis, and Spectroscopic Characterization

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)]


Published in:
Organic Letters, 6, 18, 3183-3186
Year:
2004
Keywords:
Note:
CAN 141:314608
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
1523-7060
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:




 Record created 2010-11-25, last modified 2018-03-17


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