Enzyme Catalyzed Synthesis of Some Vinyl Drug Esters in Organic Medium

Preparative Biochemistry and Biotechnology

Volumn 34, Issue 1, 2004, Pages 97-107

  Lv, De Shui ^a   Xue, Xing Tao ^a   Wang, Na ^a   Wu, Qi ^a   Lin, Xian Fu ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Acyclovir; Bacillus subtilis; Chloramphenicol; Lipozyme; Vinyl drug esters

Indexed keywords

ACICLOVIR; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT; CHLORAMPHENICOL; DRUG DERIVATIVE; ESTER; IMMOBILIZED ENZYME; LIPOZYME; SOLVENT; SUBTILISIN; TRIACYLGLYCEROL LIPASE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ENZYME SPECIFICITY; INFRARED SPECTROPHOTOMETRY; SYNTHESIS;

ACYCLOVIR; ANTI-BACTERIAL AGENTS; ANTIVIRAL AGENTS; CATALYSIS; CHLORAMPHENICOL; ENZYMES, IMMOBILIZED; ESTERS; LIPASE; MOLECULAR STRUCTURE; SOLVENTS; SPECTROPHOTOMETRY, INFRARED; SUBSTRATE SPECIFICITY; SUBTILISINS; VINYL COMPOUNDS;

BACILLUS SUBTILIS;

EID: 1542288200     PISSN: 10826068     EISSN: None     Source Type: Journal    
DOI: 10.1081/PB-120027117     Document Type: Article

References (19)

1. Gross, R.A.; Klumar, A.; Kalra, B. Polymer synthesis by in vitro enzyme catalysis. Chem. Rev. 2001, 101, 2097-2124.
2. Zaks, A.; Klibanov, A.M. Enzymatic catalysis in organic media at 100°C. Science 1984, 224, 1249-1251.
3. Wu, Q.; Lu, D.S.; Cai, Y.; Xue, X.T.; Chen, Z.C.; Lin, X.F. Regio- and stereo-selective synthesis of vinyl glucose ester catalyzed by an alkaline protease of Bacillus subtilis. Biotechnol Lett. 2001, 23, 1981-1985.
4. Wu, Q.; Feng, J.Y.; Feng, C.G.; Lu, D.S.; Lin, X.F. Enzymatic regioselective synthesis of vinyl lactose ester and its chemical polymerization. Chin. Chem. Lett. 2002, 13 (5), 416-419.
5. Xue, X.T.; Lu, D.S.; Chen, Z.C.; Wu, Q.; Cai, Y.; Lin, X.F. Enzyme-catalyzed transesterification of unusual substrate: synthesis of acyclovir and L-ascorbic acid (vitamin C) vinyl esters. Chin. Chem. Lett. 2003, 14 (2), 163-166.
6. Wagstaff, A.J.; Faulds, D.; Goa, K.L. Aciclovir. A reappraisal of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs 1994, 47, 153-205.
7. Christopher, M.; Martin, J.S.; Nigel, R.P. Synthesis and antiviral activity of acyclovir-5′-(phenyl methoxy alaninyl) phosphate as a possible membrane-soluble nucleotide prodrug. Bioorg. Med. Chem. Lett. 2000, 10, 645-647.
8. Christian, P.; Gilles, G.; Girardet, J.L.; Brent, E.K.; Imbach, J.L. The S-acyl-2-thioethyl pronucleotide approach applied to acyclovir. Part I. Synthesis and in vitro anti-hepatitis B virus activity of bis(S-acyl-2- thioethyl)phosphotriester derivatives of acyclovir. Antivir. Res. 1999, 40, 167-178.
9. Hatanaka, K.; Takeshige, H.; Kanno, K.; Maruyama, A.; Oishi, J.; Kajihara, Y.; Hashinmoto, H. New polymeric inhibitor of galactosyl transferase. J. Carbohydr. Chem. 1997, 16, 667-672.
10. Kitagawa, M.; Fan, H.; Raku, T.; Kurane, R.; Tokiwa, Y. Preparation of vinyl thymidine ester catalyzed by protease and its chemical polymerization. Biotechnol Lett. 2000, 22, 883-886.
11. Powell, D.A.; Nahata, M.C. Chloramphenicol: new perspectives on an old drug. Drug Intel. Clin. Pharm. 1982, 16, 295-300.
12. Ceriotti, G.; Defranceschi, A.; Zamboni, V. Farmaco 1954, 9, 21-38.
13. El-Kersh, T.A.; Plourde, J.R. J. Antibiot. 1976, 29, 292-302.
14. Ottolina, G.; Carrea, G.; Riva, S.J. Synthesis of ester derivatives of chloramphenicol by lipase-catalysed transesterification in organic solvents. J. Org. Chem. 1990, 55, 2366-2369.
15. John, E.D.M.; Henry, W.S.; Robert, J.P. Technology of the synthesis divinyl esters of dicarboxylic acids. Brit 1960, 827, 718.
16. 13C-Nuclear magnetic resonance spectra of O-acylglucose. Additivity of shift parameters and its application to structure elucidations. Chem. Pharm. Bull. 1980, 28, 2065-2076.
17. Chulalaksananukul, W.; Condoret, J.S.; Combes, D. Kinetics of gerany acetate synthesis by lipase transesterification in n-hexane. Enzyme. Microb. Technol. 1992, 14, 293-298.
18. Claon, P.A.; Akoh, C.C. Lipase catalyzed acidolysis of tristearin with oleic or caprylic acids to produce structured lipids. J. Am. Oil. Chem. Soc. 1994, 71, 575-578.
19. Daugs, E.D. The preparation and isolation of chloramphenicol palmitate in toluene. Org. Process Res. Dev. 2000, 4, 301-304.