Anatoli I. Zinchenko

Synthesis of 2-Chloro-2′-Deoxyadenosine by Microbiological Transglycosylation

Abstract The title compound have been synthesized by an enzymatic trans-2′-deoxyribosylation of 2-chloroadenine using the whole cells of E. coli BMT-1D/1A as a biocatalyst and 2′-deoxyguanosine as a donor of glycosyl moiety.

1-Deaza and 3-deazapurines in the reaction of microbiological transglycosylation

SummarySubstrate activity of 1- and 3-deazapurines in the reaction of microbiological ribo- 2-deoxyribosylation catalysed by purine nucleoside phosphorylase of viable cells ofE. coli BMT-1D/1A has been studied. Guanosine or 2′-deoxyguanosine were used as donors. 1-Deazapurines are good substrates in both reactions; 3-deazapurines are very effective intransdeoxyribosylation but not intransribosylation. Benzimidazole is an excellent substrate in both reactions indicating that N(1) and N(3) are not essential for transglycosylation.

Benzimidazoles in the Reaction of Enzymatic Transglycosylation

Abstract Substrate activity of a broad spectrum of derivatives of benzimidazole in the reaction of enzymatic ribo- and 2-deoxyribosylation catalyzed by purine nucleoside phosphorylase of whole cells of E. coli BMT-1D/1A has been studied. Guanosine or 2′-deoxyguanosine were used as glycosyl donors.

Microbiological synthesis of 5-ethyl- and (E)-5-(2-bromovinyl)-2′-deoxyuridine

SummaryThe title compounds were prepared by an enzymatic transdeoxyribosylation from 2′ dGuo or 2′ dThd to the respective heterocyclic bases, 5-ethyluracil and (E)-5-(2-bromovinyl)uracil, using the whole bacterial cells ofEscherichia coli as a biocatalyst.

Chemo‐Enzymatic Synthesis of 3‐Deoxy‐β‐D‐ribofuranosyl Purines

9-(3-Deoxy-β-D-erythro-pentofuranosyl)-2,6-diaminopurine (6) was synthesized by an enzymatic transglycosylation of 2,6-diaminopurine (2) with 3′-deoxycytidine (1) as a donor of 3-deoxy-D-erythro-pentofuranose moiety. This transformation comprises i) deamination of 1 to 3′-deoxyuridine (3) under the action of whole cell (E. coli BM-11) cytidine deaminase (CDase), ii) the phosphorolytic cleavage of 3 by uridine phosphorylase (UPase) giving rise to the formation of uracil (4) and 3-deoxy-α-D-erythro-pentofuranose-1-O-phosphate (5), and iii) coupling of the latter with 2 catalyzed by whole cell (E. coli BMT-4D/1A) purine nucleoside phosphorylase (PNPase). Deamination of 6 by adenosine deaminase (ADase) gave 3′-deoxyguanosine (7). Treatment of 6 with NaNO2 afforded 9-(3-deoxy-β-D-erythro-pentofuranosyl)-2-amino-6-oxopurine (3′-deoxyisoguanosine; 8). Schiemann reaction of 6 (HF/HBF4+NaNO2) gave 9-(3-deoxy-β-D-erythro-pentofuranosyl)-2-fluoroadenine (9).

An improved method for the enzymatic transformation of nucleosides into 5'-monophosphates.

An improved method to transform nucleosides into 5′-monophosphates using nucleoside phosphotransferase from Erwinia herbicola is reported. The method is based on the shift in the equilibrium state of the reaction to the formation of desired product due to its precipitation by Zn2+. Under optimal conditions, the extent of nucleoside transformations into nucleoside-5′-monophosphates were 41–91% (mol).

Chemo-enzymatic synthesis of 3-deoxy-beta-D-ribofuranosyl purines and study of their biological properties.

Abstract 9-(3-Deoxy-β-d-erythro-pentofuranosyl)-2,6-diaminopurine (2) was synthesized by an enzymatic transglycosylation of 2,6-diaminopurine using 3′-deoxycytidine (1) as a donor of the sugar moiety. Nucleoside 2 was transformed to 3′-deoxy guanosine (3), 9-(3-deoxy-β-d-erythro-pentofuranosyl)-2-amino-6-oxopurine (3′-deoxyisoguanosine; 4), and 9-(3-deoxy-β-d-erythro-pentofuranosyl)-2-fluoroadenine (5). Compounds 2–5 were evaluated for their anti-HIV activity.

Enzymatic synthesis of 2′-deoxyadenosine

SummaryThe title compound was prepared by a two step enzymatic procedure consisting of DNA hydrolysis to the mixture of 2′-deoxynucleosides followed by a transdeoxyribosilation of exogenous adenine.

Enzymatic synthesis of ATP from RNA and adenine

SummaryThe title compound was prepared by a three-stage enzymatic procedure consisting of (i) RNA hydrolysis to a mixture of ribonucleosides using intact mycelium of Spicaria violacea, (ii) transribosylation of exogenous adenine employing whole cells of Escherichia coli as a biocatalyst, and (iii) conversion of formed adenosine into ATP by the enzymes of alcohol fermentation and the kinases extracted from bakers yeast.