Linked Life Data

6848491

Source:http://linkedlifedata.com/resource/pubmed/id/6848491

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
1
pubmed:dateCreated
1983-2-14
pubmed:abstractText
We have previously presented evidence for the formation of 1-O-alkyl dihydroxyacetone-P from acyl dihydroxyacetone-P via the initial formation of an intermediate 1-O-acyl endiol of acyl dihydroxyacetone-P. This reaction involves a stereospecific exchange of the pro-R hydrogen of the acyl dihydroxyacetone-P moiety without change in configuration. The fatty acid is replaced by a long chain fatty alcohol which retains the oxygen of the primary carbinol. In the absence of fatty alcohol, water substitutes and the product is dihydroxyacetone-P which has also exchanged the pro-R hydrogen with a hydrogen from the medium. An absolute requirement of the proposed mechanism is that the loss of the fatty acid must proceed via an unusual cleavage of the dihydroxyacetone-P C-1 to oxygen bond instead of the usual cleavage at the fatty acid acyl to oxygen bond. In the present investigation, we have synthesized hexadecanoyl dihydroxyacetone-P containing oxygen-18 exclusively at the dihydroxyacetone-P C-1 oxygen. Using this substrate, we have shown that cleavage of hexadecanoyl dihydroxyacetone-P at the C-1 to oxygen bond is linked to O-alkyl dihydroxyacetone-P synthesis. Inhibition of O-alkyl lipid synthesis by means of magnesium or NADPH inhibited the unusual cleavage. At the same time, we have shown that there was hydrolysis of acyl dihydroxyacetone-P which proceeded by the usual mechanism and which was not related to synthesis of O-alkyl dihydroxyacetone-P.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Jan
pubmed:issn
0021-9258
pubmed:author
pubmed:issnType
Print
pubmed:day
10
pubmed:volume
258
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
136-42
pubmed:dateRevised
2007-11-14
pubmed:meshHeading
pubmed:year
1983
pubmed:articleTitle
The mechanism of ether bond formation in O-alkyl lipid synthesis in Ehrlich ascites tumor. Unusual cleavage of the fatty acid moiety of acyl dihydroxyacetone phosphate.
pubmed:publicationType
Journal Article, Research Support, U.S. Gov't, P.H.S., Research Support, U.S. Gov't, Non-P.H.S.