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C33-、C35-和C39-多甲藻素的合成及其光谱特征。

Syntheses of C33-, C35-, and C39-peridinin and their spectral characteristics.

作者信息

Kajikawa Takayuki, Hasegawa Shinji, Iwashita Takashi, Kusumoto Toshiyuki, Hashimoto Hideki, Niedzwiedzki Dariusz M, Frank Harry A, Katsumura Shigeo

机构信息

Department of Chemistry, School of Science and Tchnology, Kwansei Gakuin University, Gakuen, Sanda, Hyogo 669-1337, Japan.

出版信息

Org Lett. 2009 Nov 5;11(21):5006-9. doi: 10.1021/ol901940g.

DOI:10.1021/ol901940g
PMID:19795872
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3650678/
Abstract

Peridinin, a nor-carotenoid, exhibits an exceptionally high energy transfer efficiency to chlorophyll a in photosynthesis in the sea. This efficiency would be related to the unique structure of peridinin. To answer the question of why peridinin possesses the irregular C37 skeleton, we have achieved the synthesis of three peridinin derivatives. Their ultrafast time-resolved optical absorption and Stark spectra measurements have shown the presence of the characteristic intramolecular charge transfer state and the featured electrostatic properties of peridinin.

摘要

多甲藻素是一种去甲类胡萝卜素,在海洋光合作用中,它对叶绿素a的能量转移效率极高。这种效率可能与多甲藻素独特的结构有关。为了回答多甲藻素为何具有不规则C37骨架这一问题,我们合成了三种多甲藻素衍生物。它们的超快时间分辨光吸收和斯塔克光谱测量结果表明,存在特征性的分子内电荷转移态以及多甲藻素特有的静电性质。

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Syntheses of C33-, C35-, and C39-peridinin and their spectral characteristics.C33-、C35-和C39-多甲藻素的合成及其光谱特征。
Org Lett. 2009 Nov 5;11(21):5006-9. doi: 10.1021/ol901940g.
2
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本文引用的文献

1
Effect of pi-electron conjugation length on the solvent-dependent S(1) lifetime of peridinin.π电子共轭长度对多甲藻素溶剂依赖性S(1)寿命的影响
Chem Phys Lett. 2008 Sep 22;463(1-3):219-224. doi: 10.1016/j.cplett.2008.08.056.
2
Syntheses of allene-modified derivatives of peridinin toward elucidation of the effective role of the allene function in high energy transfer efficiencies in photosynthesis.合成多甲藻素的丙二烯修饰衍生物以阐明丙二烯官能团在光合作用中高效能量转移中的作用。
Org Biomol Chem. 2009 Sep 21;7(18):3723-33. doi: 10.1039/b907456b. Epub 2009 Jul 13.
3
Probing the effect of the binding site on the electrostatic behavior of a series of carotenoids reconstituted into the light-harvesting 1 complex from purple photosynthetic bacterium Rhodospirillum rubrum detected by stark spectroscopy.通过斯塔克光谱法探究结合位点对一系列重组到来自红螺菌的光合捕光1复合体中的类胡萝卜素静电行为的影响。
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4
Total synthesis of peridinin and related C37-norcarotenoid butenolides.多甲藻黄素及相关C37-去甲类胡萝卜素丁烯内酯的全合成。
Chemistry. 2007;13(4):1273-90. doi: 10.1002/chem.200600959.
5
Local electrostatic field induced by the carotenoid bound to the reaction center of the purple photosynthetic bacterium Rhodobacter sphaeroides.与球形红细菌紫色光合细菌反应中心结合的类胡萝卜素所诱导的局部静电场。
J Phys Chem B. 2005 Jan 20;109(2):992-8. doi: 10.1021/jp046929d.
6
The charge-transfer character of the S0 --> S2 transition in the carotenoid peridinin is revealed by Stark spectroscopy.通过斯塔克光谱法揭示了类胡萝卜素多甲藻素中S0→S2跃迁的电荷转移特性。
J Phys Chem B. 2005 Aug 18;109(32):15589-97. doi: 10.1021/jp052027g.
7
Total synthesis of the light-harvesting carotenoid peridinin.光捕获类胡萝卜素多甲藻素的全合成。
Angew Chem Int Ed Engl. 2006 Jun 12;45(24):4023-7. doi: 10.1002/anie.200600502.
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Stereocontrolled total synthesis of a polyfunctional carotenoid, peridinin.多官能团类胡萝卜素多甲藻素的立体控制全合成。
J Org Chem. 2004 Nov 12;69(23):7949-59. doi: 10.1021/jo048852v.
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Highly efficient stereocontrolled total synthesis of the polyfunctional carotenoid peridinin.多官能团类胡萝卜素多甲藻素的高效立体控制全合成。
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10
Structural basis of light harvesting by carotenoids: peridinin-chlorophyll-protein from Amphidinium carterae.类胡萝卜素捕光的结构基础:来自卡氏前沟藻的多甲藻叶绿素蛋白复合体
Science. 1996 Jun 21;272(5269):1788-91. doi: 10.1126/science.272.5269.1788.