Resemblance of Carbocycle Formation from Carbohydrates between Archaea and Eucarya/Eubacteria. Biosynthesis of Calditol, the Characteristic Lipid-Content Molecule in Sulfolobus acidocaldarius

Noriaki Yamauchi, Hideyoshi Ueoka, Norisuke Kamada, Tatsushi Murae

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)771-778
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume77
Issue number4
DOIs
Publication statusPublished - Apr 1 2004

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Biosynthesis
Deuterium
Carbohydrates
Lipids
Glucose
Molecules
Oxidation
Inositol
Ether
Labeling
Chemical activation
Substrates
Experiments

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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title = "Resemblance of Carbocycle Formation from Carbohydrates between Archaea and Eucarya/Eubacteria. Biosynthesis of Calditol, the Characteristic Lipid-Content Molecule in Sulfolobus acidocaldarius",
abstract = "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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T1 - Resemblance of Carbocycle Formation from Carbohydrates between Archaea and Eucarya/Eubacteria. Biosynthesis of Calditol, the Characteristic Lipid-Content Molecule in Sulfolobus acidocaldarius

AU - Yamauchi, Noriaki

AU - Ueoka, Hideyoshi

AU - Kamada, Norisuke

AU - Murae, Tatsushi

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