Structure determination and MSn analysis of two new lissoclinamides isolated from the Indo-Pacific ascidian Lissoclinum patella:: NOE restrained molecular dynamics confirms the absolute stereochemistry derived by degradative methods

被引：33

作者：

Morris, LA

van den Bosch, JJK

Versluis, K

Thompson, GS

Jaspars, M ^{[1
]}

机构：

[1] Univ Aberdeen, Dept Chem, Marine Nat Prod Lab, Old Aberdeen AB24 3UE, Scotland

[2] Univ Utrecht, Fac Pharm, Untrecht Inst Pharmaceut Sci, Dept Biomol Mass Spect, NL-3508 TB Utrecht, Netherlands

[3] Univ Utrecht, Fac Chem, Bijvoet Ctr Biomol Res, Dept Biomol Mass Spect, NL-3508 TB Utrecht, Netherlands

[4] Univ Leeds, Sch Biochem, Astbury Ctr Struct Mol Biol, Leeds LS2 9JT, W Yorkshire, England

来源：

TETRAHEDRON | 2000年 / 56卷 / 42期

基金：

英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会; 美国国家卫生研究院;

关键词：

lissoclinamide; patellamide C; stereochemistry;

D O I：

10.1016/S0040-4020(00)00746-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new lissoclinamides, lissoclinamides 9 and 10 were isolated from an Indonesian collection of the ascidian Lissoclinum patella along with the known patellamide C. The structures of the lissoclinamides were determined by a combination of 2D NMR, selective 1D TOCSY, MS and MSn techniques. The assignment of absolute stereochemistry was achieved by the hydrolysis of lissoclinamides 9 and 10 followed by chiral TLC. In the case of lissoclinamide 9, NOE restrained molecular dynamics studies were also performed confirming the proposed stereochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8345 / 8353

页数：9

共 29 条

[1] H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].