USP Electronic Research Repository

Two Distinct Conformers of the Cyclic Heptapeptide Phakellistatin 2 Isolated from the Fijian Marine Sponge Stylotella aurantium

Tabudravu, Jioji N. and Jaspars, Marcel and Morris, Linda A. and Bosch, J. Jantina Kettenes-van den and Smith, Nigel (2002) Two Distinct Conformers of the Cyclic Heptapeptide Phakellistatin 2 Isolated from the Fijian Marine Sponge Stylotella aurantium. The Journal of Organic Chemistry, 67 (24). pp. 8593-8601. ISSN 0022-3263

Full text not available from this repository.

Abstract

The isolation, structure determination, and solution conformation of two conformers of the cyclic heptapeptide phakellistatin 2 (cyclo-[Phe1-cis-Pro2-Ile3-Ile4-cis-Pro5-Tyr6-cis-Pro7]) isolated from the Fijian marine sponge Stylotella aurantium are reported. The conformers can be isolated separately by HPLC and are stable in methanol solution over a period of weeks as determined by NMR. Their NMR spectra and mass spectral fragmentation patterns differ significantly. Their solution conformations were determined by NOE-restrained molecular dynamics calculations and indicated that the two conformers had different folds, hydrogen bonding patterns, and solvent accessible surfaces. These factors may contribute to the independent stability of the two conformers, and may explain the variable biological activity previously reported for phakellistatin 2.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Q Science > QH Natural history > QH301 Biology
Divisions: Faculty of Science, Technology and Environment (FSTE) > School of Biological and Chemical Sciences
Depositing User: Repo Editor
Date Deposited: 06 Jun 2017 14:33
Last Modified: 04 Jul 2017 11:40
URI: http://repository.usp.ac.fj/id/eprint/9932
UNSPECIFIED

Actions (login required)

View Item