Substrate Specificities of Several Prenyl Chain Elongating Enzymes with Respect to 4-Methyl-4-pentenyl Diphosphate

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概要

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• In order to develop synthetic methods for biologically active homoallylic terpene sulfates, we examined the applicability and substrate specificities of several prenyl chain elongating enzymes with respect to 4-methyl-4-pentenyl diphosphate (homoIPP).The reaction of dimethylallyl diphosphate with homoIPP by use of Bacillus stearothermophilus (all-trans)-farnesyl diphosphate synthase resulted in efficient yields of cis-(yield: 45.9%) and trans-4,8-dimethylnona-3,7-dien-1-ol (homoGOH, 25.5%), which has a carbon skeleton of 4,8-dimethylnona-3-en-1-sulfate, an antiproliferative compound from a marine organism (Aiello, A. et al., Tetrahedron, 53, 11489–11492 (1997)). The homoIPP was found to be also active as a homoallylic substrate in place of isopentenyl diphosphate for Sulfolobus acidocaldarius geranylgeranyl diphosphate synthase to give diphosphate of cis- and trans-4,8,12-trimethyltrideca-3,7,11-trien-1-ol, for Micrococcus luteus B-P 26 hexaprenyl diphosphate synthase to give cis- and trans-4,8,12,16-tetramethylheptadeca-3,7,11,15-tetraen-1-ol (homoGGOH), and for Micrococcus luteus B-P 26 undecaprenyl diphosphate synthase to give cis-homoGGOH exclusively.

• 社団法人 日本農芸化学会の論文
• 2004-10-23

著者

• Koyama Tanetoshi

  Institute of Multidisciplinary Research for Advanced Materials, Tohoku University

• Nishino Tokuzo

  Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University

• 西野 朋子

  Department Of Biochemistry And Department Of Molecular Biology Nippon Medical School

• Nishino Takeshi

  日本医科大学 医科生物科学

• Nishino T

  Department Of Biochemistry And Engineering Faculty Of Engineering Tohoku University

• Nishino Tokuzo

  Dep. Of Biochemistry And Engineering Fac. Of Engineering Tohoku Univ.

• 古山 種俊

  東北大 多元物質科研

• KAWAKAMI Jun

  Department of Materials Science and Technology, Faculty of Science and Technology, Hirosaki Universi

• Kawakami Jun

  Graduate School Of Science And Technology Hirosaki University

• NAGAKI Masahiko

  Department of Materials Science and Technology, Faculty of Science and Technology, Hirosaki Universi

• MIKI Yohei

  Department of Materials Science and Technology, Faculty of Science and Technology, Hirosaki Universi

• NAKADA Minori

  Department of Materials Science and Technology, Faculty of Science and Technology, Hirosaki Universi

• KITAHARA Haruo

  Department of Natural Science, Faculty of Education, Hirosaki University

• MAKI Yuji

  Department of Biological and Material Chemistry, Faculty of Science, Yamagata University

• GOTOH Yoshinori

  Department of Biological and Material Chemistry, Faculty of Science, Yamagata University

• Nishino Takeshi

  Dept Of Biochem Univ Of California Riverside Usa

• Nishino Takeshi

  Department Of Microbiology Kyoto Pharmaceutical University

• Koyama Tanetoshi

  Institute For Chemical Reaction Science Tohoku University

• Kitahara Haruo

  Department Of Natural Science Faculty Of Education Hirosaki University

• Nishino Tokuzo

  Department Of Biochemistry And Engineering Faculty Of Engineering Tohoku University

• Maki Yuji

  Dep. Of Biological And Material Chemistry Fac. Of Sci. Yamagata Univ.

• NAGAKI Masahiko

  Graduate School of Science and Technology, Hirosaki University

• Nakada Minori

  Department Of Frontier Materials Chemistry Faculty Of Science And Technology Hirosaki University

• Maki Yuji

  Department Of Biological And Material Chemistry Faculty Of Science Yamagata University

• Kawakami Jun

  Department Of Chemistry Faculty Of Science Hirosaki University

• Nagaki Masahiko

  Graduate School Of Science And Technology Hirosaki University

• Gotoh Yoshinori

  Department Of Biological And Material Chemistry Faculty Of Science Yamagata University

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