Literature DB >> 19707676

Syntheses of allene-modified derivatives of peridinin toward elucidation of the effective role of the allene function in high energy transfer efficiencies in photosynthesis.

Takayuki Kajikawa1, Kazuyoshi Aoki, Ram Shanker Singh, Takashi Iwashita, Toshiyuki Kusumoto, Harry A Frank, Hideki Hashimoto, Shigeo Katsumura.   

Abstract

Peridinin is known as the main light-harvesting pigment in photosynthesis in the sea and exhibits exceptionally high energy transfer efficiencies to chlorophyll a. This energy transfer efficiency is thought to be related to the intricate structure of peridinin, which possesses allene and ylidenbutenolide functions in the polyene backbone. There are, however, no studies on the relationship between the structural features of peridinin and its super ability for energy transfer. We then focused on the subjects of why peridinin possesses a unique allene group and how the allene function plays a role in the exceptionally high energy transfer. Toward elucidation of the exact role of the allene function, we now describe the syntheses of three relatively unstable allene-modified derivatives of peridinin along with the results of the Stark spectroscopy of peridinin and the synthesized peridinin derivatives.

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Year:  2009        PMID: 19707676      PMCID: PMC3655548          DOI: 10.1039/b907456b

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  13 in total

1.  Highly efficient stereocontrolled total synthesis of the polyfunctional carotenoid peridinin.

Authors:  Noriyuki Furuichi; Hirokazu Hara; Takashi Osaki; Hajime Mori; Shigeo Katsumura
Journal:  Angew Chem Int Ed Engl       Date:  2002-03-15       Impact factor: 15.336

2.  Total synthesis of paracentrone, C31-allenic apo-carotenoid.

Authors:  Yusuke Murakami; Masayuki Nakano; Takuya Shimofusa; Noriyuki Furuichi; Shigeo Katsumura
Journal:  Org Biomol Chem       Date:  2005-03-11       Impact factor: 3.876

3.  The Stille reaction in the synthesis of the C37-norcarotenoid butenolide pyrrhoxanthin. Scope and limitations.

Authors:  Belén Vaz; Marta Domínguez; Rosana Alvarez; Angel R de Lera
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

4.  Structural basis of light harvesting by carotenoids: peridinin-chlorophyll-protein from Amphidinium carterae.

Authors:  E Hofmann; P M Wrench; F P Sharples; R G Hiller; W Welte; K Diederichs
Journal:  Science       Date:  1996-06-21       Impact factor: 47.728

5.  Carotenoid to chlorophyll energy transfer in the peridinin-chlorophyll-a-protein complex involves an intramolecular charge transfer state.

Authors:  Donatas Zigmantas; Roger G Hiller; Villy Sundstrom; Tomas Polivka
Journal:  Proc Natl Acad Sci U S A       Date:  2002-12-16       Impact factor: 11.205

6.  Molecular topology of the photosynthetic light-harvesting pigment complex, peridinin-chlorophyll a-protein, from marine dinoflagellates.

Authors:  P S Song; P Koka; B B Prézelin; F T Haxo
Journal:  Biochemistry       Date:  1976-10-05       Impact factor: 3.162

7.  Total synthesis of peridinin and related C37-norcarotenoid butenolides.

Authors:  Belén Vaz; Marta Domínguez; Rosana Alvarez; Angel R de Lera
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

8.  Stereocontrolled total synthesis of a polyfunctional carotenoid, peridinin.

Authors:  Noriyuki Furuichi; Hirokazu Hara; Takashi Osaki; Masayuki Nakano; Hajime Mori; Shigeo Katsumura
Journal:  J Org Chem       Date:  2004-11-12       Impact factor: 4.354

9.  Local electrostatic field induced by the carotenoid bound to the reaction center of the purple photosynthetic bacterium Rhodobacter sphaeroides.

Authors:  Kazuhiro Yanagi; Madoka Shimizu; Hideki Hashimoto; Alastair T Gardiner; Aleksander W Roszak; Richard J Cogdell
Journal:  J Phys Chem B       Date:  2005-01-20       Impact factor: 2.991

10.  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.

Authors:  Katsunori Nakagawa; Satoru Suzuki; Ritsuko Fujii; Alastair T Gardiner; Richard J Cogdell; Mamoru Nango; Hideki Hashimoto
Journal:  J Phys Chem B       Date:  2008-07-10       Impact factor: 2.991

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  3 in total

1.  Stark Absorption Spectroscopy of Peridinin and Allene-Modified Analogues.

Authors:  Toshiyuki Kusumoto; Tomoko Horibe; Takayuki Kajikawa; Shinji Hasegawa; Takashi Iwashita; Richard J Cogdell; Robert R Birge; Harry A Frank; Shigeo Katsumura; Hideki Hashimoto
Journal:  Chem Phys       Date:  2006-03-31       Impact factor: 2.348

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

Authors:  Takayuki Kajikawa; Shinji Hasegawa; Takashi Iwashita; Toshiyuki Kusumoto; Hideki Hashimoto; Dariusz M Niedzwiedzki; Harry A Frank; Shigeo Katsumura
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

Review 3.  Total Syntheses of Pladienolide-Derived Spliceosome Modulators.

Authors:  Jaehoon Sim; Eunbin Jang; Hyun Jin Kim; Hongjun Jeon
Journal:  Molecules       Date:  2021-09-30       Impact factor: 4.411

  3 in total

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