The chemical constitution of carcinolipin

Abstract

1. The neutral portion of the molecule of carcinolipin was found to be cholesterol by comparison of mixed melting points with cholesterol, its dibromide and its acetate. 2. The fatty acid present in carcinolipin was subjected to oxidative degradation by chromic acid and permanganate. Butan-2-one was the main neutral degradation product resulting from both these procedures. A mixture of dibasic acids was obtained after the oxidation with chromic acid. Permanganate oxidation yielded a complete homologous series of branched-chain C(5)-C(17) fatty acids. 3. The mass spectrum of the acid was characteristic for a saturated C(17) acid. The alcohol prepared by lithium aluminium hydride reduction of the original acid showed a mass spectrum typical for an anteiso compound. 4. Comparison of mixed melting points, gas-liquid-chromatographic behaviour and mass spectra of the fatty acid isolated from carcinolipin with an authentic sample of 14-methylhexadecanoic acid demonstrated the identity of these compounds. Cholesterol esters synthesized from authentic cholesterol and the fatty acid isolated from carcinolipin or synthetic 14-methylhexadecanoic acid showed an identical stimulating effect on the incorporation of labelled algal-protein hydrolysate into rat liver transfer RNA in vitro. 5. Mass spectra, results of oxidative degradations and comparisons with an authentic sample, as well as biological activity of the synthetic cholesterol 14-methylhexadecanoate, provided good evidence that carcinolipin is cholesterol (+)-14-methylhexadecanoate.

The role of cholesteryl 14-methylhexadecanoate in peptide elongation reactions

“…GTP (sodium salt) was purchased from Koch-Light Laboratories, Colnbrook, Bucks., U.K. Poly(U) was a product of Calbiochem, Los Angeles, Calif., U.S.A. All solvents were redistilled before use. Cholesteryl (+)-14-methylhexadecanoate was synthesized as described earlier (Hradec & Dolejs, 1968;Hradec & Dusek, 1969 Isolation and purification of elongation factors. Elongation factors from both rat liver and human tonsils were prepared essentially by the methods of Bermek, Kramer, Monkemeyer & Matthaei (1970) and Bermek & Matthaei (1970a).…”

“…GTP (sodium salt) was purchased from Koch-Light Laboratories, Colnbrook, Bucks., U.K. Poly(U) was a product of Calbiochem, Los Angeles, Calif., U.S.A. All solvents were redistilled before use. Cholesteryl (+)-14-methylhexadecanoate was synthesized as described earlier (Hradec & Dolejs, 1968;Hradec & Dusek, 1969 (1970a). In this procedure both factors are precipitated from the postmicrosomal supernatant (fraction II) by (NH4)2SO4 (35-70% of saturation) (fraction III).…”

Mass spectra of branched long‐chain aliphatic alcohols

“…The mass spectrum of 16-methylheptadecan-1-01 has been discussed by Ryhage and Stenhagen.l The spectrum contains in addition to the peaks at mle 3 An intense [M -741 peak is characteristic of long-chain primary alcohols. Its intensity is higher than that of the homologous olefinic peaks [M -881 and [M -601.…”

Influence of selected sugars and temperature on fatty acids composition in Candida tropicalis

“…This paper is concerned with the effect of various sugars on the amounts of odd-chain fatty acids in C. tropicalis grown at different temperatures, since similar studies are notably limited in literature. 7.0 g KH,P04, 2.0 g Na,HPO,, 1.5 g MgSO, ' 7 H,O, 0.1 g CaCI, ' 6 H,O, 0.01 g FeCI, . 6 H,O and 0.001 g ZnSO, and the pH was adjusted to 6.0.…”