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

Mikhailopulo, Igor A.; Zinchenko, A. I.; Bokut, S. B.; Дудчик, Н. В.; Baraj, V. N.; Kalinichenko, Еlena N.; Rosemeyer, H.; Seela, Frank

doi:10.1007/bf01020623

Cited by 14 publications

(20 citation statements)

References 20 publications

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“…Mikhailopulo et al (34) have used whole cells (E. coli BMT-1D/1A) which contain a highly active purine nucleoside phosphorylase for transferring the pentosyl moiety from guanosine or 2Ј-deoxyguanosine to 1-and 3-deaza and 1,3-dideazapurines and proved that N-1 or N-3 are not essential for transglycosylation. Whole cells of various bacteria (including Enterobacter aerogenes, Escherichia coli, Erwinia herbicola, and Aeromonas salmonicida), containing high percentage of nucleoside phosphorylase are capable of transferring the arabinofuranosyl moiety from arabinofuranosyluracil to adenine (17).…”

Section: Scheme 2 Schemementioning

confidence: 99%

Nucleoside Synthesis Mediated by Glycosyl Transferring Enzymes

Prasad

Trikha

Parmar

1999

Bioorganic Chemistry

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Section: Scheme 2 Schemementioning

confidence: 99%

Nucleoside Synthesis Mediated by Glycosyl Transferring Enzymes

Prasad

Trikha

Parmar

1999

Bioorganic Chemistry

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“…These findings have been successfully used in the synthesis of 9-(b-d-arabinofuranosyl)guanine (ara-G), employing 1-(b-d-arabinofuranosyl)cytosine (ara-C) as a donor of the arabinofuranose residue and guanosine (Guo) or 2'-deoxyguanosine (dGuo) as depot forms of guanine via a cascade of enzymatic reactions [18]. The second strain, E. coli BMT-1D/1A, proved to be somewhat more efficient in the synthesis of a) thymidine, using either i) dGuo, 2'-deoxycytidine (dCyd), or 2'-deoxyadenosine (dAdo), or ii) a mixture of the same 2'-deoxynucleosides resulting from an enzymatic hydrolysis of DNA as donors of 2-deoxyribofuranose moiety [20], b) dAdo [21], c) a panel of ribo-and 2-deoxyribofuranosides of 1-deaza-and 3-deazapurines [22] and benzimidazoles [22] [23], and d) 2-chloro-2'-deoxyadenosine (cladribine) [24]. Finally, a slightly modified strain, E. coli BMT-4D/1A, was found to be essentially more efficient vs. the parent E. coli BMT-1D/ 1A in the synthesis of 2'-deoxy-2'-fluoroguanosine [25] and 2,6-diamino-9-(3-deoxy-bd-erythro-pentofuranosyl)purine [26].…”

mentioning

confidence: 99%

A Universal Biocatalyst for the Preparation of Base- and Sugar-Modified Nucleosides via an Enzymatic Transglycosylation

Barai

Zinchenko

Eroshevskaya

et al. 2002

HCA

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Dedicated to Prof. Dr. Wolfgang Pfleiderer on the occasion of his 75th birthdayThe E. coli BMT-4D/1A cells have been selected according to Munch-Petersen et al. They carry two regulatory mutations (cytR and deoR) and are able to synthesize constitutively nucleoside-catabolizing enzymes, e.g., cells that possess high UPase and PNPase activities. The cells have been cross-linked by glutaraldehyde to afford a biocatalyst that retained high UPase and PNPase activities and was comfortable for repeated use. An incubation of 2'-deoxyguanosine (1) and 2-chloroadenine (2) (molar ratio 3 : 1) in Kphosphate buffer (10 mm ; pH 7.0) in the presence of the biocatalyst at 658 for 7 h resulted in quantitative transformation of 2 into 2-chloro-2'-deoxyadenosine (4; cladribine) that was isolated in 81% yield (Scheme 1). Similarly, the reaction of guanosine (5) and 1,2,4-triazole-3-carboxamide (6) (molar ratio 1 : 1) in K-phosphate buffer (10 mm ; pH 7.0) in the presence of the biocatalyst at 608 for 30 h led to the formation of 1-(b-dribofuranosyl)-1,2,4-triazole-3-carboxamide (8; ribavirin) in 90 ± 92% yield (67 ± 70% isolated yield) (Scheme 2).Introduction. ± Nucleoside analogues are a mainstream in the treatment of many viral infections and play a significant role in the chemotherapy of different malignancies [1 ± 4]. Most of them are produced by chemical methods employing the natural nucleosides as starting compounds, or by a convergent approach via the condensation of the carbohydrate precursor and heterocyclic base. The latter strategy suffers from many drawbacks, most serious of which are the low stereospecificity of the glycosidic-bond formation and ambiguous regiospecificity, especially in the case of purine bases. As a result, chemical schemes of nucleoside-analogue preparation are rather complicated and accompanied by a tedious isolation of the individual desired compounds [5].Considerable progress in the preparation of nucleoside analogues under consideration was achieved by combination of chemical methods and biochemical transformations (for reviews, see [6]). The enzymatic equilibrium-transfer reaction of the sugar moiety of one nucleoside to the heterocyclic base was discovered by Krenitsky in the 60×s [7] [8]. It was established that this equilibrium reaction is catalyzed by purine nucleoside phosphorylase (PNPase) in the case of purine nucleosides and purine bases, and by uridine (thymidine) phosphorylases (UPase or TPase) in the case of pyrimidine nucleosides and pyrimidines. More than a decade later, it was shown that this reaction can be used for the preparation of base-and sugar-modified nucleosides [9 ± 13].

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“…~ The 1-deazapurine nucleosides, such as l-deaza-2'-deoxyadenosine (la) [l] [2] (purine numbering is used throughout the General Part) or the ribonucleoside lb [3] [4] can form Hoogsteen base pairs within oligonucleotide duplexes [2] [5]. The synthesis of 1 -deazapurine deoxyribonucleosides can be performed by i) deoxygenation of ribonucleosides [l], ii) the microbial transglycosylation of imidazo [4,5-b]pyridine bases [6] [7], and iii) the stereoselective glycosylation of the nucleobases with sugar halides [8] [9]. In the following, we report on the nucleobase-anion glycosylation of 6-substituted 1-deazapurines and their conversion into the nucleosides 2a-d or 3a-d.…”

mentioning

confidence: 99%

Synthesis of 6‐Substituted 1‐Deazapurine 2′‐Deoxyribonucleosides

Wenzel¹,

Seela²

1996

Helvetica Chimica Acta

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(4.X.95)The synthesis of 6-substituted 1 -deazapurine 2-deoxyribonucleosides is described. Glycosylation of the 1-deazapurine (imidazo[4,5-h]pyridine) anions with the a -o-halogenose 5 gives stereoselectively N7-and N9-regioisomers. 'H-NMR NOE and ' k -N M R spectroscopy are used for unambiguous assignment of isomers, and "N-NMR chemical shifts are correlated with uPara Hummett constants and point charges.

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

Cited by 14 publications

References 20 publications

Nucleoside Synthesis Mediated by Glycosyl Transferring Enzymes

Nucleoside Synthesis Mediated by Glycosyl Transferring Enzymes

A Universal Biocatalyst for the Preparation of Base- and Sugar-Modified Nucleosides via an Enzymatic Transglycosylation

Synthesis of 6‐Substituted 1‐Deazapurine 2′‐Deoxyribonucleosides

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