Unnatural enantiomers of 5-azacytidine analogues: syntheses and enzymatic properties.
2'-Deoxy-beta-L-5-azacytidine(L-Decitabine), beta-L-5-azacytidine, and derivatives were stereospecifically prepared starting from L-ribose or L-xylose. D- and L-enantiomers of 2'-deoxy-beta-5-azacytidine were weak substrates of human recombinant deoxycytidine kinase (dCK), whereas both enantiomers of beta-5-azacytidine or the L-xylo-analogues were not substrates of the enzyme. None of the reported derivatives of beta-L-5-azacytidine was a substrate of human recombinant cytidine deaminase (CDA).
Gaubert
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G
UMR 5625 du CNRS, Département de Chimie, Université Montpellier II, Place Bataillon, 34095 Montpellier, France.
Gosselin
G
G
Eriksson
S
S
Vita
A
A
Maury
G
G
D001374:Azacitidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D000077209:Decitabine; D003842:Deoxycytidine Kinase / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D013237:Stereoisomerism; D013379:Substrate Specificity
D000077209:Decitabine; D003842:Deoxycytidine Kinase; D001374:Azacitidine