Acetyl Coenzyme AによるSphinganineの非酵素的N-アセチル化
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Dihydroceramide, a biosynthetic precursor of ceramide, is biologically synthesized from sphinganine and fatty acyl-CoA with acyl-CoA: sphinganine N-acyltransferase. Interestingly, the sphinganine was found to be N-acetylated with acetyl CoA in the absence of the equine brain protein in an organic solvent or mild alkaline solution. The structure of the acetylated product, that sphinganine was acetylated with at the C2-amino residue, was characterized with spectra of NMR, negative FAB-MS, GC-MS, and GLC, as well as NaIO4-oxidation when occuring in conjunction with those of chemically synthesized, authentic N-acetylated sphinganine. The non-enzymatic reactions of the sphinganine with other fatty acyl-CoAs were markedly less than those with acetyl CoA. Compared to the reaction of sphinganine with acetyl CoA, the reaction of sphingenine with acetyl CoA was not reactive, but the reaction of phytosphingosine with acetyl CoA reacted with 78.1% of the yield from the sphinganine with acetyl CoA. In contrast, the non-enzymatic reaction was interfered with by added protein. These results suggest that a saturated carbon chain with free C2-amino residue in the long chain base structure could be required from the occurence of N-acetylation, especially at C4 and C5. Non-enzymatic synthesis of the N-acetyl sphinganine (dihydro-C2-ceramide) would be important in relation to apoptosis for cells. Since the dihydro-C2-ceramide might be a precursor of C2-ceramide, the possibility of the conversion was examined in the reaction of dihydroceramide desaturase in vitro. The assay system of the desaturase was established herein, revealing inconvertibility and this phenomena suggests the impossibility of the generation of C2-cer-amide in vivo.
- 1996-10-01
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