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Issue 0, 1968
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Microbiological oxidation of long-chain aliphatic compounds. Part II. Branched-chain alkanes

Abstract

In a medium containing glucose, the yeast Torulopsis gropengiesseri converts long-chain methyl-branched alkanes into glycolipids by one or more of three metabolic pathways, namely, (i) alkane alkan-1-ol alkanoic acid ω- and/or ω-1-hydroxyalkanoic acid glycolipid, (ii) alkane alkan-1-ol glycolipid, and (iii) alkane alkan-1-ol ω- and/or ω-1-hydroxyalkan-1-ol glycolipid. Pathways (ii) and (iii) are important for the metabolism of alkan-1-ols whose dehydrogenation to alkanoic acids is inhibited by one or more methyl substituents close to the primary alcohol group. Initial oxidation of 2,2-dimethylhexadecane occurs exclusively at the less hindered terminal position which is the predominant site of the initial oxidation of 2-methyl-hexadecane. Alkanoic acids and alkan-1-ols which have methyl substituents close to the functional group give ω- and ω-1-hydroxy-derivatives; alkanoic acids and alkan-1-ols which have methyl substituents at the ω-1-position give ω-hydroxy-derivatives.

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Article information


J. Chem. Soc. C, 1968, 2809-2815
Article type
Paper

Microbiological oxidation of long-chain aliphatic compounds. Part II. Branched-chain alkanes

D. F. Jones, J. Chem. Soc. C, 1968, 2809
DOI: 10.1039/J39680002809

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