Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Organic and Biological
Resemblance of Carbocycle Formation from Carbohydrates between Archaea and Eucarya/Eubacteria. Biosynthesis of Calditol, the Characteristic Lipid-Content Molecule in Sulfolobus acidocaldarius
Noriaki YamauchiHideyoshi UeokaNorisuke KamadaTatsushi Murae
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2004 Volume 77 Issue 4 Pages 771-778


We investigated the biosynthesis of the unique structure of calditol, a part of the characteristic lipid molecules in the major part of thermophilic archaea, Sulfolobus sp. Deuterium-labeling experiments with deuterated glucose substrates, were carried out. The results clarified that calditol was biosynthesized from glucose with C–C bond formation between C-1 and C-5, and no loss of deuterium at C-6 of glucose was observed. Two reaction mechanisms were possible when these experimental findings, and conventional reports were considered. Among these, the course that assumes C-4 oxidation as the starting point would be preferable from the resemblance to myo-inositol biosynthesis. Furthermore, the high deuterium incorporation at C-1 of calditol from C-1 of glucose suggests that activation, such as oxidation at C-1, is not involved in the ether C–O bonding.

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© 2004 The Chemical Society of Japan
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