Occurrence of nonenzymatic N-acetylation of sphinganine with acetyl coenzyme A producing C2-H2-ceramide and its inconvertibility to apoptotic C2-ceramide.
Sphinganine, a biosynthetic precursor of ceramide, was non-enzymatically acetylated with acetyl coenzyme A at the C-2-amino residue to produce C2-H2-ceramide (N-acetyl sphinganine) in an organic solvent and in an aqueous solution with a high yield, whereas sphingenine was only acetylated slightly. The structure of the N-acetyl sphinganine was identified with mass spectrum, and with chromatography using an authentic N-acetylated substance. Furthermore, the C2-H2-ceramide was examined for enzymatic desaturation to determine whether C2-ceramide, a cell-permeable ceramide responsible for apoptosis of cells, was produced, revealing an inferior substrate for H2-ceramide desaturase of horse brain microsomes.
Kashiwagi
M
M
Department of Biochemistry, Sapporo Medical University School of Medicine, Japan.
Mikami
T
T
Chiba
M
M
Chiba
S
S
Matsumoto
H
H
Akino
T
T
Gasa
S
S
D000105:Acetyl Coenzyme A / Q000378:metabolism*; D000107:Acetylation; D000818:Animals; D017209:Apoptosis; D001921:Brain / Q000378:metabolism / Q000648:ultrastructure; D002518:Ceramides / Q000737:chemistry / Q000378:metabolism*; D006736:Horses; D008861:Microsomes / Q000378:metabolism; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism
D002518:Ceramides; D000105:Acetyl Coenzyme A; D013110:Sphingosine; C005682:safingol