Defining a process operating window for the synthesis of 5-methyluridine by transglycosylation of guanosine and thymine

Journal of Biotechnology

Volumn 151, Issue 1, 2011, Pages 108-113

  Gordon, Gregory E R ^a   Visser, Daniel F ^a   Brady, Dean ^a   Raseroka, Nelly ^a   Bode, Moira L ^a  

^a CSIR Biosciences   (South Africa)

Author keywords

5 Methyluridine; Antiretroviral; Biocatalysis; Cascade reaction; Nucleoside phosphorylase

Indexed keywords

5-METHYLURIDINE; ANTIRETROVIRALS; BIOCATALYSIS; CASCADE REACTIONS; NUCLEOSIDE PHOSPHORYLASE;

BACTERIOLOGY; BIOMOLECULES; ESCHERICHIA COLI; PHOSPHORYLATION;

SYNTHESIS (CHEMICAL);

5 METHYLURIDINE; GUANOSINE; POTASSIUM DIHYDROGEN PHOSPHATE; PURINE NUCLEOSIDE PHOSPHORYLASE; THYMINE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE; URIDINE PHOSPHORYLASE;

ARTICLE; BACILLUS; BACILLUS HALODURANS; BIOCATALYSIS; ENZYME SUBSTRATE; ESCHERICHIA COLI; GLYCOSYLATION; NONHUMAN; PH; PRIORITY JOURNAL; PURINE SYNTHESIS; SOLUBILITY; TEMPERATURE SENSITIVITY;

BACILLUS; BIOREACTORS; GLYCOSYLATION; GUANOSINE; HYDROGEN-ION CONCENTRATION; PURINE-NUCLEOSIDE PHOSPHORYLASE; TEMPERATURE; THYMINE; URIDINE; URIDINE PHOSPHORYLASE;

BACILLUS HALODURANS;

EID: 78650678548     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2010.11.013     Document Type: Article

References (30)

1. Atiemo-Obeng V.A., Penney W.R., Armenante P. Solid-liquid mixing. Industrial Mixing-Science and Practice 2004, 543-582. Wiley-Interscience, New Jersey. E.L. Paul, V.A. Atiemo-Obeng, S.M. Kresta (Eds.).
2. Bunton C.A., Humeres E. The hydrolyses of α-d-ribose and α-d-glucose-1-phosphate. J. Org. Chem. 1969, 34:572-576.
3. Bzowska A., Kulikowska E., Shugar D. Purine nucleoside phosphorylases: properties, functions, and clinical aspects. Pharmacol. Ther. 2000, 88:364-425.
4. Chen B.-C., Quinlan S.L., Stark D.R., Reid J.G., Audia V.H., George J.G., Eisenreich E., Brundidge S.P., Racha S., Spector R.H. 5′-Benzoyl-2′α-bromo-3′-O-methanesulfonylthymidine: a superior nucleoside for the synthesis of the anti-AIDS drug d4T (stavudine). Tetrahedron Lett. 1995, 36:7957-7960.
5. Chen B.-C., Quinlan S.L., Reid J.G. A new synthesis of the anti-AIDS drug AZT from 5-methyluridine. Tetrahedron Lett. 1995, 36:7961-7964.
6. Chen B.-C., Quinlan S.L., Stark D.R., Reid J.G., Spector R.H. A new thymine free synthesis of the anti-AIDS drug d4T via regio/stereo controlled β-elimination of bromoacetates. Tetrahedron Lett. 1998, 39:729-732.
7. Colombié S., Gaunand A., Lindet B. Lysozyme inactivation and aggregation in stirred-reactor. J. Mol. Catal. B: Enzym. 2001, 11:559-565.
8. Findrik Z., Vasić-Rački D. Biotransformation of d-methionine into l-methionine in the cascade of four enzymes. Biotechnol. Bioeng. 2007, 98:956-967.
9. Hori N., Watanabe M., Yamazaki Y., Mikami Y. Synthesis of 5-methyluridine by a thermophile Bacillus stearothermophilus JTS 859. Agric. Biol. Chem. 1989, 53:197-202.
10. Hori N., Watanabe M., Yamazaki Y., Mikami Y. Purification and characterization of thermostable purine nucleoside phosphorylase from Bacillus stearothermophilus JTS 859. Agric. Biol. Chem. 1989, 53:2205-2210.
11. Hori N., Watanabe M., Sunagawa K., Uehara K., Mikami Y. Production of 5-methyluridine by immobilized thermostable purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase from Bacillus stearothermophilus JTS 859. J. Biotechnol. 1991, 17:121-131.
12. Hori N., Watanabe M., Mikami Y. The effects of organic solvent on the ribosyl transfer reaction by thermostable purine nucleoside phosphorylase and pyrimidine nucleoside phosphorylase from Bacillus stearothermophilus JTS 859. Biocatal. Biotransform. 1991, 4:297-304.
13. Hori N., Uehara K., Mikami Y. Effects of xanthine-oxidase on synthesis of 5-methyluridine by the ribosyl transfer-reaction. Agric. Biol. Chem. 1991, 55:1071-1074.
14. Ishii M., Shirae H., Yokozeki K. Enzymatic production of 5-methyluridine from purine nucleosides and thymine by Erwinia carotovora AJ-2992. Agric. Biol. Chem. 1989, 53:3209-3218.
15. Joshi J.B., Sawant S.B., Patwardhan A.W., Patil D.J., Kshatriya S.S., Nere N.K. Relation between flow pattern and de-activation of enzymes in stirred reactors. Chem. Eng. Sci. 2001, 56:443-452.
16. Kline P.C., Schramm V.L. Purine nucleoside phosphorylase inosine hydrolysis, tight binding of the hypoxanthine intermediate, and third-the-sites reactivity. Biochemistry 1992, 31:5964-5973.
17. Krajewska E., Shugar D. Pyrimidine ribonucleoside phosphorylase activity vs. 5- and/or 6-substituted uracil and uridine analogues, including conformational aspects. Biochem. Pharmacol. 1982, 31:1097-1102.
18. Leer J.C., Hammer-Jespersen K., Schwartz M. Uridine phosphorylase from Escherichia coli. Physical and chemical characterization. Eur. J. Biochem. 1977, 75:217-224.
19. Pollard D.J., Woodley J.M. Biocatalysis for pharmaceutical intermediates: the future is now. Trends Biotechnol. 2007, 25:66-73.
20. Shiragami H., Ineyama T., Uchida Y., Izawa K. Synthesis of 1-(2,3-dideoxy-β-d-glycero-pent-2-enofuranosyl)thymine (d4T, stavudine) from 5-methyluridine. Nucleosides Nucleotides 1996, 15:47-58.
21. Steenkamp L., Brady D. Optimisation of stabilised carboxylesterase NP for enantioselective hydrolysis of naproxen methyl ester. Process Biochem. 2008, 43:1419-1426.
22. Straathof A.J.J., Panke S., Schmid A. The production of fine chemicals by biotransformations. Curr. Opin. Biotechnol. 2002, 13:548-556.
23. Utagawa T., Morisawa H., Yoshinaga F., Yamazaki A., Mitsugi K. Microbiological synthesis of adenine arabinoside. Agric. Biol. Chem. 1985, 49:1053-1058.
24. UNAIDS, 2008. Report on the global AIDS epidemic.
25. Visser D.F., Hennessy F., Rashamuse K., Louw M.E., Brady D. Cloning, purification and characterisation of a recombinant purine nucleoside phosphorylase from Bacillus halodurans Alk36. Extremophiles 2010, 14:185-192.
26. Visser D.F., Rashamuse K.J., Hennessy F., Gordon G.E.R., van Zyl P.J., Mathiba K., Bode M.L., Brady D. High yielding cascade enzymatic synthesis of 5-methyluridine using a novel combination of nucleoside phosphorylases. Biocatal. Biotransform. 2010, 28:245-253.
27. Wilson L.J., Liotta D. A general method for controlling glycosylation stereochemistry in the synthesis of 2′-deoxyribose nucleosides. Tetrahedron Lett. 1990, 31:1815-1818.
28. Wilson L.J., Hager M.W., El-Kattan Y.A., Liotta D.C. Nitrogen glycosylation reactions involving pyrimidine and purine nucleoside with furanoside sugars. Synthesis 1995, 12:1465-1479.
29. Wolff A., Zhu L., Kielland V., Straathof A.J.J., Jongejan J.A., Heijnen J.J. Simple dissolution-reaction model for enzymatic conversion of suspension of solid substrate. Biotechnol. Bioeng. 1997, 56:433-440.
30. Woodley J.M. Choice of biocatalyst form for scalable processes. Biochem. Soc. Trans. 2006, 34:301-303.