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Org Lett. 2016 Feb 5;18(3):512-5. doi: 10.1021/acs.orglett.5b03546. Epub 2016 Jan 12.

Absolute Configuration of Hydroxysqualene. An Intermediate in Bacterial Hopanoid Biosynthesis.

Author information

1
Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.

Abstract

Squalene (SQ) is a key intermediate in hopanoid biosynthesis. Many bacteria synthesize SQ from farnesyl diphosphate (FPP) in three steps: FPP to (1R,2R,3R)-presqualene diphosphate (PSPP), (1R,2R,3R)-PSPP to hydroxysqualene (HSQ), and HSQ to SQ. Chemical, biochemical, and spectroscopic methods were used to establish that HSQ synthase synthesizes (S)-HSQ. In contrast, eukaryotic squalene synthase catalyzes solvolysis of (1R,2R,3R)-PSPP to give (R)-HSQ. The bacterial enzyme that reduces HSQ to SQ does not accept (R)-HSQ as a substrate.

PMID:
26756303
DOI:
10.1021/acs.orglett.5b03546
[Indexed for MEDLINE]

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