Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells

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Title:Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells
Creators:
Votruba, Ivan
Holý, Antonín
Dvořáková, Hana
Günter, Jaroslav
Hocková, Dana
Hřebabecký, Hubert
Cihlar, Tomas
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 59, 10, pp. 2303-2330

Abstract

<p>Alginate gel-entrapped cells of auxotrophic thymine-dependent strain of <i>E. coli</i> catalyze the transfer of 2-deoxy-D-ribofuranosyl moiety of 2'-deoxyuridine to purine and pyrimidine bases as well as their aza and deaza analogs. All experiments invariably gave β-anomers; in most cases, the reaction was regiospecific, affording <i>N</i><sup>9</sup>-isomers in the purine and <i>N</i><sup>1</sup>-isomers in the pyrimidine series. Also a 2,3-dideoxynucleoside can serve as donor of the glycosyl moiety. The acceptor activity of purine bases depends only little on substitution, the only condition being the presence of <i>N</i><sup>7</sup>-nitrogen atom. On the other hand, in the pyrimidine series the activity is limited to only a narrow choice of mostly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases containing amino groups are deaminated; this can be avoided by conversion of the base to the corresponding <i>N</i>-dimethylaminomethylene derivative which is then ammonolyzed. The method was verified by isolation of 9-(2-deoxy-β-D-ribofuranosyl) derivatives of adenine, guanine, 2-chloroadenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenine, 3-deazaadenine, 1-(2-deoxy-β-D-ribofuranosyl) derivatives of 5-ethyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-β-D-pentofuranosyl)hypoxanthine, 9-(2,3-dideoxy-β-D-pentofuranosyl)-6-methylpurine, and other nucleosides.

Title:Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells
Creators:
Votruba, Ivan
Holý, Antonín
Dvořáková, Hana
Günter, Jaroslav
Hocková, Dana
Hřebabecký, Hubert
Cihlar, Tomas
Masojídková, Milena
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:59
Number:10
Page Range:pp. 2303-2330
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19942303UNSPECIFIED
ID Code:652
Item Type:Article
Deposited On:06 Feb 2009 17:02
Last Modified:06 Feb 2009 16:02

Citation

Votruba, Ivan; Holý, Antonín; Dvořáková, Hana; Günter, Jaroslav; Hocková, Dana; Hřebabecký, Hubert; Cihlar, Tomas; Masojídková, Milena (1994) Synthesis of 2-Deoxy-β-D-ribonucleosides and 2,3-Dideoxy-β-D-pentofuranosides on Immobilized Bacterial Cells. Collection of Czechoslovak Chemical Communications, 59 (10). pp. 2303-2330. ISSN 0010-0765

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