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Literature DB >> 19795872

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

Takayuki Kajikawa¹, Shinji Hasegawa, Takashi Iwashita, Toshiyuki Kusumoto, Hideki Hashimoto, Dariusz M Niedzwiedzki, Harry A Frank, Shigeo Katsumura.

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.

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Year: 2009 PMID： 19795872 PMCID： PMC3650678 DOI： 10.1021/ol901940g

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

11 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. The charge-transfer character of the S0 --> S2 transition in the carotenoid peridinin is revealed by Stark spectroscopy.

Authors: Lavanya Premvardhan; Emmanouil Papagiannakis; Roger G Hiller; Rienk van Grondelle
Journal: J Phys Chem B Date: 2005-08-18 Impact factor: 2.991

3. Total synthesis of the light-harvesting carotenoid peridinin.

Authors: Thomas Olpp; Reinhard Brückner
Journal: Angew Chem Int Ed Engl Date: 2006-06-12 Impact factor: 15.336

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. 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

6. 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

7. 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

8. 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

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

Authors: Takayuki Kajikawa; Kazuyoshi Aoki; Ram Shanker Singh; Takashi Iwashita; Toshiyuki Kusumoto; Harry A Frank; Hideki Hashimoto; Shigeo Katsumura
Journal: Org Biomol Chem Date: 2009-07-13 Impact factor: 3.876

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

5 in total

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

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

2. The charge-transfer character of the S0 --> S2 transition in the carotenoid peridinin is revealed by Stark spectroscopy.

3. Total synthesis of the light-harvesting carotenoid peridinin.

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

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

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

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

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

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

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.

1. The nature of the intramolecular charge transfer state in peridinin.

2. Stereoretentive Suzuki-Miyaura coupling of haloallenes enables fully stereocontrolled access to (-)-peridinin.

3. Excited state properties of a short π-electron conjugated peridinin analogue.

4. Triplet state spectra and dynamics of peridinin analogs having different extents of pi-electron conjugation.

Review 5. The unique photophysical properties of the Peridinin-Chlorophyll-α-Protein.