醛霉素，一种来自链霉菌的新型抗微生物抗生素。III. 绝对构型的测定。

Aldecalmycin, a new antimicrobial antibiotic from Streptomyces. III. Determination of absolute configuration.

作者信息

Sawa R, Takahashi Y, Nakamura H, Nakamura K T, Naganawa H, Takeuchi T

机构信息

Institute of Microbial Chemistry, Tokyo, Japan.

出版信息

J Antibiot (Tokyo). 1994 Nov;47(11):1280-3. doi: 10.7164/antibiotics.47.1280.

DOI:10.7164/antibiotics.47.1280

PMID:8002391

Abstract

The planar structure of aldecalmycin (1) had been determined in the previous paper, together with the conformations of the substituted trans decalin ring having one double bond and the sugar: beta-glucopyranoside type. The absolute configuration of 1 was a following problem to be solved. X-Ray crystallographic analysis of crystalline 4'-6'-O-benzylidenedihydroaldecalmycin (4) revealed the relative configuration. On the other hand, the stereoisomerism of the sugar was determined to be D by the optical rotation value of tetra-O-acetyl-alpha-methylglucopyranoside derived from 1. These results established the absolute configuration of 1.

摘要

醛卡霉素（1）的平面结构已在之前的论文中确定，同时还确定了具有一个双键的取代反式十氢萘环和糖（β-D-吡喃葡萄糖苷型）的构象。1的绝对构型是接下来需要解决的问题。对结晶的4'-6'-O-亚苄基二氢醛卡霉素（4）进行X射线晶体学分析揭示了其相对构型。另一方面，通过由1衍生得到的四-O-乙酰-α-甲基吡喃葡萄糖苷的旋光值确定糖的立体异构为D型。这些结果确定了1的绝对构型。