Bicyclic peptides. VI. Synthesis, conformation, and ion-binding of two bicyclic nonapeptides.

作者信息

Zanotti G C, Campbell B E, Easwaran K R, Blout E R

机构信息

Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, MA.

出版信息

Int J Pept Protein Res. 1988 Dec;32(6):527-35. doi: 10.1111/j.1399-3011.1988.tb01384.x.

DOI:10.1111/j.1399-3011.1988.tb01384.x

PMID:3246477

Abstract

Two related homodetic bicyclic nonapeptides (cyclo Glu-X-Pro-Gly-Lys-X-Pro-Gly)-cyclo (l gamma----5 epsilon), X = Ala(BCP2), X = Leu(BCP3) have been synthesized using conventional solution phase methods involving mixed anhydride coupling reactions starting with appropriately protected naturally occurring amino acids. The conformation and ion binding properties of BCP2 have been studied by nuclear magnetic resonance and circular dichroism techniques. The results of these studies have been compared to those of BCP3. The presence of Ala caused both Ala-Pro bonds to be trans in free BCP2. This characteristic imparted subtle differences to the ion-binding properties of BCP2 as compared to free BCP3 which has one cis Leu-Pro bond and one trans Leu-Pro bond.

摘要

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