具有 B 环还原叶绿素 π 系统的合成细菌叶绿素-d 类似物的自聚集。

Self-aggregation of synthetic bacteriochlorophyll-d analogues possessing a B-ring reduced chlorin pi-system.

机构信息

Department of Bioscience and Biotechnology, Faculty of Science and Engineering, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan.

出版信息

J Org Chem. 2009 Nov 6;74(21):8437-40. doi: 10.1021/jo901586u.

DOI:10.1021/jo901586u

PMID:19791736

Abstract

Zinc 3(1)-hydroxy-13(1)-oxo-chlorophyll derivatives 3 and 4 having a B-ring reduced chlorin pi-system (C7-C8, C17=C18) were prepared as models of self-aggregative bacteriochlorophyll-d, which are regioisomers of 1 and 2 possessing a natural-type D-ring reduced chlorin pi-system (C7=C8, C17-C18). 3(1)-Epimerically pure forms of secondary alcohol 3 (3-CH(OH)CH(3)) as well as primary alcohol 4 (3-CH(2)OH) were effectively synthesized by modifying naturally available bacteriochlorophyll-a. Self-aggregation of 3 and 4 in an aqueous micellar solution was examined by UV-vis and CD spectroscopies and compared with that of their regioisomeric 1 and 2.

摘要

锌 3(1)-羟基-13(1)-氧代叶绿素衍生物 3 和 4 具有 B 环还原的叶绿素 π 系统（C7-C8，C17=C18），它们是自聚集的细菌叶绿素-d 的模型，是具有天然型 D 环还原的叶绿素 π 系统（C7=C8，C17-C18）的 1 和 2 的区域异构体。通过修饰天然存在的细菌叶绿素-a，有效地合成了仲醇 3（3-CH(OH)CH(3)）和伯醇 4（3-CH(2)OH）的 3(1)-差向异构体纯形式。通过紫外可见光谱和 CD 光谱研究了 3 和 4 在水胶束溶液中的自聚集，并与它们的区域异构体 1 和 2 进行了比较。