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Synthesis and biosynthetic utilization of radioactive photoreactive fatty acids.

1982; Elsevier BV; Volume: 257; Issue: 24 Linguagem: Inglês

10.1016/s0021-9258(18)33313-1

1083-351X

Pierre Leblanc, John P. Capone, Gerhard E. Gerber,

Lipid metabolism and biosynthesis

A synthesis of a homologous series of highly radioactive photoreactive fatty acids has been developed.Oxidative cleavage of the cis double bonds of unsaturated fatty acids by NaI04/0s04 produced the w-oxo fatty acids; subsequent reduction by C3H]NaBH4 afforded a series of highly radioactive [w-3H]hydroxy fatty acids to which a variety of photoreactive probes can be readily attached.In this study, the m-diazirinophenoxy group was coupled to the w-hydroxy groups of the fatty acids, yielding the w-( m-diazirinophenoxy) derivatives of nonanoic, undecanoic, tridecanoic, and pentadecanoic acid.These photoreactive derivatives were incorporated by L-cells into their major phospholipids; in addition, a number of proteins were shown to be acylated by these fatty acids.The photoreactive group was shown to remain intact as indicated by the cross-linking of the resulting photoreactive phospholipids to other phospholipids as well as to a number of L-cell proteins upon photolysis.This procedure thus identifies integral membrane proteins and directly produces photoaffinity derivatives of those proteins normally acylated by fatty acids.