Synthesis of chlorophyll-a derivatives methylated in the 3-vinyl group and their intrinsic site energy

被引：14

作者：

Tamiaki, Hitoshi ^{[1
]}

Tsuji, Kazuki ^{[1
,2
]}

Kuno, Masaki ^{[1
]}

Kimura, Yuki ^{[1
,2
]}

Watanabe, Hiroaki ^{[1
]}

Miyatake, Tomohiro ^{[2
]}

机构：

[1] Ritsumeikan Univ, Grad Sch Life Sci, Kusatsu, Shiga 5258577, Japan

[2] Ryukoku Univ, Fac Sci & Technol, Dept Chem Mat, Otsu, Shiga 5202194, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2016年 / 26卷 / 13期

基金：

日本学术振兴会;

关键词：

Conformation; Photosynthesis; Pyropheophorbide; Visible absorption maximum; Wittig reaction; SELF-AGGREGATION; CHLORINS; DISTANCE; SOLVENT; PROTEIN; MODEL;

D O I：

10.1016/j.bmcl.2016.05.008

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Wittig reaction of methyl pyropheophorbide-d possessing the 3-formyl group gave readily methyl pyropheophorbides-a bearing a variety of 3-alkenyl groups as semi-synthetic models of chlorophyll-a. The 3-substituents rotated around the C3-C3(1) bond from the coplanar conformation with the chlorin p-system, moving the redmost visible absorption maxima to a shorter wavelength. The model experiments showed that natural chlorophyll-a carrying the 3-vinyl group would take a similar rotamer to control its intrinsic site energy. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：3034 / 3037

页数：4

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