Synthesis and conformational analysis of geodiamolide analogues

被引：13
作者：
Marimganti, Srinivasa
Wieneke, Ralph
Geyer, Armin
Maier, Martin E.
机构：
[1] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
[2] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 17期
关键词：
depsipeptides; peptidomimetics; amino acids; hydroxy acids; conformation; MARINE SPONGE; CLAISEN REARRANGEMENT; CYCLODEPSIPEPTIDE; PEPTIDE; DESIGN; ACIDS; JASPLAKINOLIDE; DEPSIPEPTIDE; JASPAMIDE; CHAIN;
D O I：
10.1002/ejoc.200700024
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Starting with the omega-hydroxy and omega-amino acid derivatives 13 and 21, the two closely related geodiamolide analogs 32 and 35, respectively, were prepared. Compared to the natural cyclodepsipeptide geodiamolide (1), the macrocycles 32 and 35 have a smaller ring size (17- vs. 18-membered). Conformational analysis by ROESY spectroscopy and molecular dynamics simulation revealed that the reduced ring size causes the polypropionate sector to flip with regard to the geodiamolide conformation. ((c) Wiley-VCH Verlag GmbH & Co.
引用
收藏
页码：2779 / 2790
页数：12
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