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Hydrophobic Interaction of Chromophoresin Visual Pigment Formation

Research Project

Project/Area Number 04640523
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionJAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY, HOKURIKU (1993)
The University of Electro-Communications (1992)

Principal Investigator

TSUJIMOTO Kazuo  JAIST, Sch.of Mate.Sci., Professor, 材料科学研究科, 教授 (50017414)

Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1993: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1992: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsRETINOCHROME / RETINAL ANALOG / beta-IONONE RING / HYDROPHOBIC INTERACTION / RHODOPSIN / CIRCULAR DICHROISM / 6S-CONFORMATION / REGIOSPECIFIC PHOTOISOMERIZATION / 質量分析 / 直鎖レチナールアナログ / 立体特異的光異性化 / 11-シスレチナール
Research Abstract

1. Hydrophobic Interaction around beta-IononeRing of Chromophores
5,6-Dihydro-, 7,8-dihydro-, alpha-, and 3,4-dehydroretinals were synthesized Pigment formation of the retinal analogs with aporetinochrome resulted in apparent completion with loose hydrophobic interaction around the beta-ionone ring.
2. Opsin Shifts of Retinal Analogs without beta-Ionone Ring
The opsin shift of the structurely linear analog, 3,7-dodecapentaenal showed 1400 cm^<-1> smaller value of the neative one, 2400 cm^<-1>.
3. The Conformation of Retinochrome Chromophore in 6S-Bond
With 6S-cis locked retinal analog, the pigment were formed as in native retinochrome formation, while 6S-trans locked analog gave no pigment.
4. Regiospecific Photoisomerization of Retinal Analogs
Photoisomerization of 3,7-DDP with aporetinochrome regiospecifically gave 11-cis typed isomer, whereas 3,7-DDT did not show the high selectivity, 43%.
5. CD Spectra of 6S-Cis Locked Retinal Analogs
The retinochrome analogs with 8,18-methano- and ethanoretinal gave intense and negative beta-band compared with positive alpha-band.
6.11-Methylretinal Analogs
11-Methyl-, 13-demethyl-11-methyl-, and 9, 13-didemethyl- 11-methylretinals were synthesized. The conformation of all-trans 11-methylretinal were determined to be 10,12-di-S-cis. Photoisomerization of these analogs with aporetinochrome furnished corresponding 11-cis isomers in more than 90% regioselectivity.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] K.Tsujimoto: "Stereoselective Photoisomerization of ψ-retinal" J.Photochem.Photobiol.65. 73-78 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] A.Wada: "Synthesis of 8,18-Ethanoretinal and Its Interaction with Apo-Retinochrome" Tetrahedron Lett.34. 1069-1072 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Kinumi: "The Conformational Analysis and Photoisomerization of Retinochrome Analogs with Polyenals" Photochem.Photobiol.58. 409-412 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Tsujimoto: "Frontiers of Photobiology" Elsevier Science Publishers B.V., 6 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Tsujimoto: "Stereoselective Photoisomerization of psi-Retianl" J.Photochem.Photobiol.65. 73-78 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] A.Wada: "Synthesis of 8,18-Ethano-retinal and its Interaction with Apo-Retinochrome." Tetrahedron Lett.34. 1069-1072 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] T.Kinumi: "The Conformational Analysis and Photoisomerization of Retinochrome Analogs with Polyenals." Photochem.Photobiol.58. 409-412 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Tsujimoto: ""Frontiers of Photobiology"" Elsevier Science Publishers. B.V.6 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Tsujimoto: "Hydrophobic Interaction between Retinal Analogues and Aporetinochrome in the Pigment Formation" Frontiers of Photobiology. 147-152 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] A.Wada: "Synthesis of 8,18-Ethanoretinal and Its Interaction with Apo-Retinochrome" Tetrahedron Lett.34. 1069-1072 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Kinumi: "The Conformational Analysis and Photoisomerization of Retinochrome Analogs with Polyenals" Photochem.Photobiol.58. 409-412 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Kinumi,K.Tsujimoto,M.Ohashi R.Hara,T.Hara,K.Ozaki,M.Sakai,Y,Katsutal,A.Wada,M.Ito: "The Conformational Analysis and Photoisomerization of Retinochrome Analogs with Polyenals" Photochem.Photobiol.(1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Tsujimoto,K.Iida,M.Miyazaki,Y.Shirasaka,M.Ohashi,M.Sheves,R.Hara,T.Hara,K.Ozaki: "Proceedings of 11th International Congress on Photobiology" Elsevier Science Publisher (Amsterdam),

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2025-11-19  

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