通过协同配位和氢键识别组氨酸与合成锌氨基氧氯调节异构体

IF 1.9 4区 化学 Q2 CHEMISTRY, ORGANIC Journal of Physical Organic Chemistry Pub Date : 2024-01-31 DOI:10.1002/poc.4602
Mio Yuasa, Nobuyuki Hara, Hitoshi Tamiaki
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引用次数: 0

摘要

以 2,3,7,8,12,13,17,18-八乙基卟啉为原料,通过调节选择性酸催化顺式-12,13-二乙基-顺式-12,13-二羟基-2-氧代卟啉的双脱水制备了 13-(N,N-二乙基氨基)甲基-3,3,7,8,12,17,18-七乙基-2-氧代卟啉锌。合成的氨基氧氯化锌在氯仿中与 Nα 保护组氨酸的咪唑基发生轴向连接,同时前者的氨基与后者的羧基发生氢键连接。由此产生的两点结合超分子可作为叶绿素与肽在光合作用装置(包括光收集天线和电荷分离反应中心)中的复合物模型。通过氨基氯化锌与具有硫醚和羧酸分子的相关蛋氨酸的相互作用,产生了类似的 1:1 复合物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Recognition of histidines with a synthetic zinc amino-oxochlorin regioisomer via synergetic coordination and hydrogen bonding

Zinc 13-(N,N-diethylamino)methyl-3,3,7,8,12,17,18-heptaethyl-2-oxochlorin was prepared from 2,3,7,8,12,13,17,18-octaethylporphyrin via the regioselectively acid-catalyzed double dehydration of cis-12,13-diethyl-cis-12,13-dihydroxy-2-oxobacteriochlorin to the corresponding 12-ethyl-13-vinyl-2-oxochlorin. The synthetic zinc amino-oxochlorin was axially ligated with the imidazolyl group of Nα-protected histidines in chloroform, and concomitantly the amino group of the former was hydrogen-bonded with the carboxy group of the latter. The resulting two-point bonding supramolecules served as models for the complexes of chlorophylls with peptides in photosynthetic apparatuses including light-harvesting antennas and charge-separating reaction centers. A similar 1:1 complex was produced by the interaction of the zinc amino-chlorin with the related methionine possessing thioether and carboxylic acid moieties.

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来源期刊
CiteScore
3.60
自引率
11.10%
发文量
161
审稿时长
2.3 months
期刊介绍: The Journal of Physical Organic Chemistry is the foremost international journal devoted to the relationship between molecular structure and chemical reactivity in organic systems. It publishes Research Articles, Reviews and Mini Reviews based on research striving to understand the principles governing chemical structures in relation to activity and transformation with physical and mathematical rigor, using results derived from experimental and computational methods. Physical Organic Chemistry is a central and fundamental field with multiple applications in fields such as molecular recognition, supramolecular chemistry, catalysis, photochemistry, biological and material sciences, nanotechnology and surface science.
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