I. Votruba et al., SYNTHESIS OF 2-DEOXY-BETA-D-RIBONUCLEOSIDES AND 2,3-DIDEOXY-BETA-D-PENTOFURANOSIDES ON IMMOBILIZED BACTERIAL-CELLS, Collection of Czechoslovak Chemical Communications, 59(10), 1994, pp. 2303-2330
Alginate gel-entrapped cells of auxotrophic thymine-dependent strain o
f E. coli 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 beta-anomers; in most
cases, the reaction was regiospecific, affording N9-isomers in the pur
ine and N1-isomers in the pyrimidine series. Also a 2,3-dideoxynucleos
ide can serve as donor of the glycosyl moiety. The acceptor activity o
f purine bases depends only little on substitution, the only condition
being the presence of N7-nitrogen atom. On the other hand, in the pyr
imidine series the activity is limited to only a narrow choice of most
ly short 5-alkyl and 5-halogeno uracil derivatives. Heterocyclic bases
containing amino groups are deaminated; this can be avoided by conver
sion of the base to the corresponding N-dimethylaminomethylene derivat
ive which is then ammonolyzed. The method was verified by isolation of
9-(2-deoxy-beta-D-ribofuranosyl) derivatives of adenine, guanine, 2-c
hlorodenine, 6-methylpurine, 8-azaadenine, 8-azaguanine, 1-deazaadenin
e, 3-deazaadenine, 1-(2-deoxy-beta-D-ribofuranosyl) derivatives of 5-e
thyluracil, 5-fluorouracil, and 9-(2,3-dideoxy-beta-D-pentofuranosyl)h
ypoxanthine, 2,3-dideoxy-beta-D-pentofuranosyl)-6-methylpurine, and ot
her nucleosides.