PMID: 7372403Feb 1, 1980Paper

Cyclic peptides. VII. Synthesis and conformation of diastereomeric analogs of cyl-2 containing L-proline and L-leucine

International Journal of Peptide and Protein Research
A YasutakeN Izumiya

Abstract

Two diastereomeric cyclic tetrapeptides with a sequence of cyclo (-D (and L)-Tyr (me)-L-Ile-L-Pro-L-Leu-) (ID and IL) have been synthesized, which are simplified analogs of a phytotoxic peptide Cyl-2, and contain an L-proline and an L-leucine residue in place of an L-pipecolic acid and a 2-amino-8-oxo-9,10-epoxydecanoic acid residue, respectively, in Cyl-2. The cyclization of the H-D-Tyr(Me)-L-Ile-L-Pro-L-Leu-ONSu proceeded smoothly to give ID in excellent yield (50%), but the cyclization of H-L-Tyr(Me)-L-Ile-L-Pro-L-Leu-ONSu gave IL in much lower yield (10%). Based on the results of 1H- and 13C-n.m.r. studies, differential N-methylation and model buildings of ID, the backbone structure of ID has been proposed to be a unique trans-trans-cis-trans conformation, the L-Ile-L-Pro bond being cis.

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