Chemical-enzymatic synthesis of 3'-amino-2',3'-dideoxy-β-D- ribofuranosides of natural heterocyclic bases and their 5'-monophosphates

Article abstract of DOI:10.1080/15257779408013281

Treatment of O²,3'-anhydro-5'-O-trityl derivatives of thymidine (1) and 2'-deoxyuridine (2) with lithium azide in dimethylformamide at 150 °C resulted in the formation of the corresponding isomeric 3'-azido-2',3'- dideoxy-5'-O-trityl-β-D-ribofuranosyl N¹- (the major products) and N³- nucleosides 3/4 and 5/6). 3'-Amino-2',3'-dideoxy-β-D-ribofuranosides of thymidine [Thd(3'NH₂)], uridine [dUrd(3'NH₂)], and cytidine [dCyd(3'NH₂)] were synthesized from the corresponding 3'-azido derivatives. The Thd(3'NH₂) and dUrd(3'NH₂) were used as donors of carbohydrate moiety in the reaction of enzymatic transglycosylation of adenine and guanine to afford dAdo(3'NH₂) and dGuo(3'NH₂). The substrate activity of dN(3'NH₂) vs. nucleoside phosphotransferase of the whole cells of Erwinia herbicola was studied.

Full text of DOI:10.1080/15257779408013281

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Nucleosides and Nucleotides
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Chemical-Enzymatic Synthesis
of 3′-Amino-2′, 3′-dideoxy-β-D-
ribofuranosides of Natural Heterocyclic
Bases and Their 5′-Monophosphates
Galina V. Zaitseva a , Evgenii I. Kvasyuk a , Elena V. Vaaks a , Vladimir
N. Barai b , Sergei B. Bokut b , Anatolii I. Zinchenko b & Igor A.
Mikhailopulo a
a Institute of Bioorganic Chemistry, Byelorussian Academy of
Sciences , 220141, Minsk, Byelorussia
b Institute of Microbiology, Byelorussian Academy of Sciences ,
220733, Minsk, Byelorussia
Published online: 23 Sep 2006.
To cite this article: Galina V. Zaitseva , Evgenii I. Kvasyuk , Elena V. Vaaks , Vladimir N. Barai , Sergei
B. Bokut , Anatolii I. Zinchenko & Igor A. Mikhailopulo (1994) Chemical-Enzymatic Synthesis of 3′-
Amino-2′, 3′-dideoxy-β-D-ribofuranosides of Natural Heterocyclic Bases and Their 5′-Monophosphates,
Nucleosides and Nucleotides, 13:1-3, 819-834, DOI: 10.1080/15257779408013281
To link to this article: http://dx.doi.org/10.1080/15257779408013281
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