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Pure and Applied Chemistry

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Functional genomics approach to the study of triterpene biosynthesis

Yutaka Ebizuka1 / Yuji Katsube1 / T. Tsutsumi1 / Tetsuo Kushiro1 / M. Shibuya1

1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan


IUPAC International Symposium on the Chemistry of Natural Products, International Symposium on the Chemistry of Natural Products, ISCNP, Natural Products, 23rd, Florence, Italy, 2002-07-28–2002-08-02

Citation Information: Pure and Applied Chemistry. Volume 75, Issue 2-3, Pages 369–374, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: 10.1351/pac200375020369, January 2009

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The Arabidopsis thaliana genome-sequencing project has identified the presence of 13 oxidosqualene cyclase homologs in this plant. In addition to the already identified clones, namely, CAS1 cycloartenol synthase, LUP1 lupeol synthase, and YUP8H12R.43 multifunctional triterpene synthase, two new cDNAs of the putative oxidosqualene cyclase genes, F1019.4 and T30F21.16, were obtained by polymerase chain reaction (PCR) and functionally expressed in yeast. Liquid chromatography/mass spectrometry (LC/MS) analysis led to the identification of some of their reaction products. Interestingly, except for CAS1 for sterol biosynthesis of primary metabolism, so-far-obtained all triterpene synthases of this plant are multifunctional, producing more than one cyclization product. A feeding experiment of 13C-labeled acetate with LUP1 lupeol synthase transformant demonstrated the stereospecific water addition to lupenyl cation intermediate, yielding 3β,20 dihydroxylupane, which accounts for the multiproduct nature of this synthase.

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