O-alkyl lipid synthesis: The mechanism of the acyl dihydroxyacetone phosphate fatty acid exchange reaction

Samuel J. Friedberg, Susan E Weintraub, Dorothy Peterson, Neera Satsangi

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

We have previously provided evidence for a mechanism by which acyl DHAP is converted enzymatically to O-alkyl DHAP. This mechanism involves, in part, the formation of an endiol of acyl DHAP, loss of the fatty acid by splitting of the DHAP carbon-1 to oxygen bond and the gain of a long chain fatty alcohol. It has been shown that acyl DHAP can exchange its fatty acid for one in the medium, presumably by the mediation of O-alkyl DHAP synthase. In the present ivestigation we have shown that the fatty acid which is gained by acyl DHAP in the exchange process retains both carboxyl oxygens, as predicted by our postulated mechanism. This reaction is exceptional because the usual action of acyl hydrolases is to cleave at the oxygen to acyl bond.

Original languageEnglish (US)
Pages (from-to)1177-1184
Number of pages8
JournalBiochemical and Biophysical Research Communications
Volume145
Issue number3
DOIs
StatePublished - Jun 30 1987

Fingerprint

Dihydroxyacetone Phosphate
Fatty Acids
Oxygen
Lipids
Fatty Alcohols
Hydrolases
Carbon

ASJC Scopus subject areas

  • Biochemistry
  • Biophysics
  • Molecular Biology

Cite this

O-alkyl lipid synthesis : The mechanism of the acyl dihydroxyacetone phosphate fatty acid exchange reaction. / Friedberg, Samuel J.; Weintraub, Susan E; Peterson, Dorothy; Satsangi, Neera.

In: Biochemical and Biophysical Research Communications, Vol. 145, No. 3, 30.06.1987, p. 1177-1184.

Research output: Contribution to journalArticle

@article{ac8d195c54774abd9bb6a6a79c418ddf,
title = "O-alkyl lipid synthesis: The mechanism of the acyl dihydroxyacetone phosphate fatty acid exchange reaction",
abstract = "We have previously provided evidence for a mechanism by which acyl DHAP is converted enzymatically to O-alkyl DHAP. This mechanism involves, in part, the formation of an endiol of acyl DHAP, loss of the fatty acid by splitting of the DHAP carbon-1 to oxygen bond and the gain of a long chain fatty alcohol. It has been shown that acyl DHAP can exchange its fatty acid for one in the medium, presumably by the mediation of O-alkyl DHAP synthase. In the present ivestigation we have shown that the fatty acid which is gained by acyl DHAP in the exchange process retains both carboxyl oxygens, as predicted by our postulated mechanism. This reaction is exceptional because the usual action of acyl hydrolases is to cleave at the oxygen to acyl bond.",
author = "Friedberg, {Samuel J.} and Weintraub, {Susan E} and Dorothy Peterson and Neera Satsangi",
year = "1987",
month = "6",
day = "30",
doi = "10.1016/0006-291X(87)91561-0",
language = "English (US)",
volume = "145",
pages = "1177--1184",
journal = "Biochemical and Biophysical Research Communications",
issn = "0006-291X",
publisher = "Academic Press Inc.",
number = "3",

}

TY - JOUR

T1 - O-alkyl lipid synthesis

T2 - The mechanism of the acyl dihydroxyacetone phosphate fatty acid exchange reaction

AU - Friedberg, Samuel J.

AU - Weintraub, Susan E

AU - Peterson, Dorothy

AU - Satsangi, Neera

PY - 1987/6/30

Y1 - 1987/6/30

N2 - We have previously provided evidence for a mechanism by which acyl DHAP is converted enzymatically to O-alkyl DHAP. This mechanism involves, in part, the formation of an endiol of acyl DHAP, loss of the fatty acid by splitting of the DHAP carbon-1 to oxygen bond and the gain of a long chain fatty alcohol. It has been shown that acyl DHAP can exchange its fatty acid for one in the medium, presumably by the mediation of O-alkyl DHAP synthase. In the present ivestigation we have shown that the fatty acid which is gained by acyl DHAP in the exchange process retains both carboxyl oxygens, as predicted by our postulated mechanism. This reaction is exceptional because the usual action of acyl hydrolases is to cleave at the oxygen to acyl bond.

AB - We have previously provided evidence for a mechanism by which acyl DHAP is converted enzymatically to O-alkyl DHAP. This mechanism involves, in part, the formation of an endiol of acyl DHAP, loss of the fatty acid by splitting of the DHAP carbon-1 to oxygen bond and the gain of a long chain fatty alcohol. It has been shown that acyl DHAP can exchange its fatty acid for one in the medium, presumably by the mediation of O-alkyl DHAP synthase. In the present ivestigation we have shown that the fatty acid which is gained by acyl DHAP in the exchange process retains both carboxyl oxygens, as predicted by our postulated mechanism. This reaction is exceptional because the usual action of acyl hydrolases is to cleave at the oxygen to acyl bond.

UR - http://www.scopus.com/inward/record.url?scp=0023668257&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023668257&partnerID=8YFLogxK

U2 - 10.1016/0006-291X(87)91561-0

DO - 10.1016/0006-291X(87)91561-0

M3 - Article

C2 - 3606600

AN - SCOPUS:0023668257

VL - 145

SP - 1177

EP - 1184

JO - Biochemical and Biophysical Research Communications

JF - Biochemical and Biophysical Research Communications

SN - 0006-291X

IS - 3

ER -