Abstract
An efficient synthesis of polymerizable 3′- and 5′-O-acyl-nucleoside derivatives has been developed from inosine and 2′-deoxyuridine by enzyme-catalyzed regioselective acylation with divinyl dicarboxylates. In acetone, Lipozyme (immobilized lipase from Mucor miehei) gave 5′-O-acyl-nucleoside products, and PPL (lipase from porcine pancreas) provided 3′-O-acyl-nucleoside products.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Carrea G, Ottolina G, Riva S (1995) Role of solvents in the control of enzyme selectivity in organic media. Trends Biotechnol. 13: 63–70.
Chu CK, Baker DC (1993) Nucleosides and Nucleotides as Antitumor and Antiviral Agents. New York: Plenum.
Degn P, Pedersen LH, Duus JQ, Zimmermann W (1999) Lipase-catalyzed synthesis of glucose fatty acid esters in tert-butanol. Biotechnol. Lett. 21: 275–280.
Ferrero M, Gotor V (2000) Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides. Chem. Rev. 100: 4319–4347.
Noritomi H, Almmarsson O, Barletta GL, Klibanov AM (1996) The influence of the mode of enzyme preparation on enzymatic enantioselectivity in organic solvents and its temperature dependence. Biotechnol. Bioeng. 51: 95–99.
Nozaki K, Uemura A, Yamashita J, Yasumoto M (1990) Enzymatic regioselective acylation of the 3'-hydroxyl groups of 2'-deoxy-5-fluorouridine (FUdR) and 2'-deoxy-5-trifiuoromethyl-uridine (CF3UdR). Tetrahedron Lett. 31: 7327–7328.
Riva S, Chopineau J, Kieboom APG, Klibanov AM (1988) Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide. J. Am. Chem. Soc. 110: 584–589.
Sinko P, Kohn J (1993) Polymeric Delivery Systems. In: El-Noklay MA, Piatt MD, Charpentier BA, eds. ACS Symposium Series 520. Washington, DC: American Chemical Society, pp. 18–42.
Uemura A, Nozaki K, Yamashita J, Yasumoto M (1989) Lipase-catalyzed regioselective acylation of sugar moieties of nucleosides. Tetrahedron Lett. 30: 3817–3818.
Wong CH, Chen ST, Hennen WJ, Bibbs JA, Wang YF, Liu JC, Pantoliano MW, Whitlow M, Bryan PN (1990) Enzymes in organic synthesis: use of Subtilisin and a highly stable mutant derived from multiple site-specific mutations. J. Am. Chem. Soc. 112: 945–953.
Yoshimoto K, Itatani Y, Tsuda Y (1980) 13C-Nuclear magnetic resonance spectra of O-acylglucose. Additivity of shift parameters and its application to structure elucidations. Chem. Pharm. Bull. 28: 2065–2074.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sun, XF., Wang, N., Wu, Q. et al. Controllable regioselective enzymatic synthesis of polymerizable 5′-O-vinyl- and 3′-O-vinyl-nucleoside analogues in acetone. Biotechnology Letters 26, 1019–1022 (2004). https://doi.org/10.1023/B:BILE.0000030050.20353.a6
Issue Date:
DOI: https://doi.org/10.1023/B:BILE.0000030050.20353.a6