Synthesis and conformational analysis of DI-13C-labeled farnesyl diphosphate analogs

被引：13
|
作者：
Zahn, TJ
Ksebati, MB
Gibbs, RA [1 ]
机构：
[1] Wayne State Univ, Coll Pharm & Allied Hlth Profess, Dept Pharmaceut Sci, Detroit, MI 48202 USA
[2] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 23期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1016/S0040-4039(98)00751-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two di-C-13-labeled farnesyl diphosphates (2 and 4) have been prepared using modified versions of the isoprenoid triflate route previously developed in this laboratory. The (3)J(CC) coupling constants far the precursor alcohols 1 and 3 are 1.6 Hz and 3.6 Hz, respectively, in CDCl3, and very similar results were obtained for 2 and 4 in D2O. This indicates a skew or gauche conformation about the C-3-C-4 bond and a trans conformation about the C-4-C-5 bond in both farnesol and FPP. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3991 / 3994
页数：4
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