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- W1570291004 abstract "Abstract An optically active (+) C30 alcohol has been isolated after hydrolysis of presqualene pyrophosphate by yeast microsomes. This alcohol can be prepared on a relatively large scale directly from farnesyl pyrophosphate in incubations with yeast microsomes from which inhibitors of phosphatase are omitted. The alcohol is named presqualene alcohol as its pyrophosphorylated form appears to be identical with natural presqualene pyrophosphate and is converted into squalene by microsomes in the presence of NADPH. The elemental compositions of presqualene alcohols biosynthesized from protio-farnesyl pyrophosphate and from [1-D2]-farnesyl pyrophosphate were found by high resolution mass spectrometry to be C30H49OH and C30H46D3OH, respectively. Presqualene alcohol contains five double bonds and one carbocycle. Mass spectral, nuclear magnetic resonance, and infrared spectroscopic studies as well as chemical degradation of presqualene alcohol indicate that its structure is that of a tetrasubstituted cyclopropane: cis-(1,2-anti-1,3-anti)-3-(2',6',10'-trimethylundeca-2',6'-10'-trienyl)-2-(2'',6''-dimethylnona-2'',6''-dienyl)-2-methyl-1-hydroxymethylcyclopropane. The data limit the absolute configuration around the three asymmetrical centers of the ring to either 1R, 2R, 3R or 1S, 2S, 3S out of the eight possible isomers." @default.
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- W1570291004 date "1971-10-01" @default.
- W1570291004 modified "2023-10-18" @default.
- W1570291004 title "Presqualene Alcohol" @default.
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- W1570291004 doi "https://doi.org/10.1016/s0021-9258(18)61783-1" @default.
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