Industrial biotransformations in the synthesis of building blocks leading to enantiopure drugs

Bioresource Technology

Volumn 115, Issue , 2012, Pages 196-207

  Munoz Solano D ^a   Hoyos, P ^a   Hernaiz M J ^a   Alcantara A R ^a   Sanchez Montero J M ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Biocatalysis; Chiral drugs; Hydrolases; Industrial scale; Oxido reductases

Indexed keywords

ATTRACTIVE STRATEGIES; BIOCATALYSIS; BIOLOGICALLY ACTIVE MOLECULES; BUILDING BLOCKES; CHIRAL COMPOUNDS; CHIRAL DRUGS; ENANTIOMERICALLY PURE COMPOUNDS; ENANTIOPURE DRUGS; GROWING DEMAND; INDUSTRIAL PROCESSS; INDUSTRIAL SCALE; LABORATORY SCALE; OXIDO-REDUCTASES; PHARMACEUTICAL INDUSTRY; SYNTHETIC PROCESS; SYNTHETIC ROUTES;

ENANTIOMERS; HYDROLASES; INDUSTRY; STEREOCHEMISTRY;

ACCIDENT PREVENTION;

6 AMINOPENICILLANIC ACID; 7 AMINOCEPHALOSPORANIC ACID; ALPHA GLUCOSIDASE INHIBITOR; ATAZANAVIR; ATORVASTATIN; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; CARBOVIR; CEPHALOSPORIN; CHEMOKINE RECEPTOR ANTAGONIST; CIPROKIREN; DILTIAZEM; DULOXETINE; HYDROLASE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; IBUPROFEN; LOTRAFIBAN; MONTELUKAST; OMAPATRILAT; OXIDOREDUCTASE; PACLITAXEL; PENICILLIN G; PHOSPHODIESTERASE INHIBITOR; PRAVASTATIN; REMIKIREN; SAXAGLIPTIN; SITAGLIPTIN; SULOPENEM; TALAMPANEL; UNINDEXED DRUG; ZANAMIVIR;

BIOTRANSFORMATION; CATALYSIS; DRUG; ENZYME ACTIVITY; PHARMACEUTICAL INDUSTRY;

BIOCATALYSIS; BIOCATALYST; BIOTRANSFORMATION; BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA; CANDIDA RUGOSA; CHIRALITY; DRUG INDUSTRY; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME KINETICS; MEMBRANE REACTOR; NONHUMAN; PRIORITY JOURNAL; RACEMIC MIXTURE; REVIEW;

BIOTRANSFORMATION; DRUG INDUSTRY; HYDROLASES; OXIDATION-REDUCTION; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM;

EID: 84861456895     PISSN: 09608524     EISSN: 18732976     Source Type: Journal    
DOI: 10.1016/j.biortech.2011.11.131     Document Type: Review

References (63)

1. Anastas P., Eghbali N. Green chemistry: principles and practice. Chem. Soc. Rev. 2010, 39:301-312.
2. Anderson B.A., Hansen M.M., Harkness A.R., Henry C.L., Vicenzi J.T., Zmijewski M.J. Application of a practical biocatalytic reduction to an enantioselective synthesis of the 5h-2, 3-Benzodiazepine Ly300164. J. Am. Chem. Soc. 1995, 117(49):12358-12359.
3. Baldwin C.V.F., Wohlgemuth R., Woodley J.M. The first 200-L scale asymmetric Baeyer-Villiger oxidation using a whole-cell biocatalyst. Org. Process Res. Dev. 2008, 12:660-665.
4. Behrens G.A., Hummel A., Padhi S.K., Schätzle S., Bornscheuer U.T. Discovery and protein engineering of biocatalysts for organic synthesis. Adv. Synth. Catal. 2011, 353(13):2191-2215.
5. Berenguer-Murcia A., Fernandez-Lafuente R. New trends in the recycling of NAD(P)H for the design of sustainable asymmetric reductions catalyzed by dehydrogenases. Curr. Org. Chem. 2010, 14:1000-1021.
6. Carballeira J.D., Quezada M.A., Hoyos P., Simeó Y., Hernaiz M.J., Alcantara A.R., Sinisterra J.V. Microbial cells as catalysts for stereoselective red-ox reactions. Biotechnol. Adv. 2009, 27:686-714.
7. Clapés P., Garrabou X. Current trends in asymmetric synthesis with aldolases. Adv. Synth. Catal. 2011, 353(13):2263-2283.
8. Chartrain M., Lynch J., Choi W.B., Churchill H., Patel S., Yamazaki S., Volante R., Greasham R. Asymmetric bioreduction of a bisaryl ketone to its corresponding (S)-bisaryl alcohol, by the yeast Rhodotorula pilimanae ATCC 32762. J. Mol. Catal. B-Enzym. 2000, 8(4-6):285-288.
9. Dawson M.J., Noble D., Mahmoudian M. Process for the Preparation of N-Acetylneuraminic Acid 2000, Glaxo Group Limited, Greenford, GB, (6156544).
10. de Carvalho C.C.C.R. Enzymatic and whole cell catalysis: finding new strategies for old processes. Biotechnol. Adv. 2011, 29(1):75-83.
11. DeSantis G., Zhu Z., Greenberg W.A., Wong K., Chaplin J., Hanson S.R., Farwell B., Nicholson L.W., Rand C.L., Weiner D.P., Robertson D.E., Burk M.J. An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives. J. Am. Chem. Soc. 2002, 124(31):9024-9025.
12. Dingler C., Ladner W., Krei G.A., Cooper B., Hauer B. Preparation of (R)-2-(4-hydroxyphenoxy) propionic acid by biotransformation. Pestic. Sci. 1996, 46(1):33-35.
13. Doswald S., Estermann H., Kupfer E., Stadler H., Walther W., Weisbrod T., Wirz B., Wostl W. Large scale preparation of chiral building blocks for the P3 site of renin inhibitors. Bioorg. Med. Chem. 1994, 2:403-410.
14. Evans C.T., Roberts S.M., Shoberu K.A., Sutherland A.G. Potential use of carbocylic nucleosides for the treatment of AIDS: chemo-enzymatic syntheses of the enantiomers of carbovir. J. Chem. Soc. Perkin Trans. 1992, 1:589-592.
15. Faber K. Biotransformations in Organic Chemistry. A Textbook 2011, Springer-Verlag, Berlin, Heidelberg. sixth ed.
16. Gill I., Patel R. Biocatalytic ammonolysis of (5S)-4, 5-dihydro-1H-pyrrole-1, 5-dicarboxylic acid, 1-(1, 1-dimethylethyl)-5-ethyl ester: Preparation of an intermediate to the dipeptidyl peptidase IV inhibitor Saxagliptin. Bioorg. Med. Chem. Lett. 2006, 16(3):705-709.
17. Goswami A., Kissick T.P. Enzymatic desymmetrization of dimethyl cylcohex-4-ene-cis-1, 2-dicarboxylate to (1S, 2R)-2-(methoxycarbonyl)cyclohex-4-ene-1-carboxylic acid. Org. Process Res. Dev. 2009, 13(3):483-488.
18. Gupta A., Tschentscher A., Bobkova M. 2-Butanol Production Method 2008, IEP GmbH, Wiesbaden, DE, (7371903).
19. Hanefeld U., Gardossi L., Magner E. Understanding enzyme immobilisation. Chem. Soc. Rev. 2009, 38(2):453-468.
20. Hollmann F., Arends I.W.C.E., Buehler K., Schallmey A., Buhler B. Enzyme-mediated oxidations for the chemist. Green Chem. 2011, 13(2):226-265.
21. Hollmann F., Arends I.W.C.E., Holtmann D. Enzymatic reductions for the chemist. Green Chem. 2011, 13(9):2285-2314.
22. Hollmann F., Lin P.C., Witholt B., Schmid A. Stereospecific biocatalytic epoxidation: the first example of direct regeneration of a FAD-dependent monooxygenase for catalysis. J. Am. Chem. Soc. 2003, 125(8209):8217.
23. Homann M.J., Vail R., Morgan B., Sabesan V., Levy C., Dodds D.R., Zaks A. Enzymatic hydrolysis of a prochiral 3-substituted glutarate ester, an intermediate in the synthesis of an NK1/NK2 dual antagonist. Adv. Synth. Catal. 2001, 343(6-7):744-749.
24. Huisman G.W., Liang J., Krebber A. Practical chiral alcohol manufacture using ketoreductases. Curr. Opin. Chem. Biol. 2010, 14(2):122-129.
25. Johanson T., Carlquist M., Olsson C., Rudolf A., Frejd T., Gorwa-Grauslund M.F. Reaction and strain engineering for improved stereo-selective whole-cell reduction of a bicyclic diketone. Appl. Microbiol. Biotechnol. 2008, 77(5):1111-1118.
26. Kaluzna I.A., Feske B.D., Wittayanan W., Ghiviriga I., Stewart J.D. Stereoselective, biocatalytic reductions of a-chloro-b-keto esters. J. Org. Chem. 2005, 70(1):342-345.
27. Kataoka M., Kotaka A., Thiwthong R., Wada M., Nakamori S., Shimizu S. Cloning and overexpression of the old yellow enzyme gene of Candida macedoniensis, and its application to the production of a chiral compound. J. Biotechnol. 2004, 114(1-2):1-9.
28. Kieslich K. Biotransformations of industrial use. Acta Biotechnol. 1991, 11(6):559-570.
29. Kim M.J., Hennen W.J., Sweers H.M., Wong C.H. Enzymes in carbohydrate synthesis - N-acetylneuraminic acid aldolase catalyzed-reactions and preparation of N-acetyl-2-deoxy-d-neuraminic acid-derivatives. J. Am. Chem. Soc. 1988, 110(19):6481-6486.
30. Kizaki N., Yasohara Y., Hasegawa J., Wada M., Kataoka M., Shimizu S. Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes. Appl. Microbiol. Biotechnol. 2001, 55(5):590-595.
31. Kosjek B., Nti-Gyabaah J., Telari K., Dunne L., Moore J.C. Preparative asymmetric synthesis of 4, 4-dimethoxytetrahydro-2H-pyran-3-ol with a ketone reductase and in situ cofactor recycling using glucose dehydrogenase. Org. Process Res. Dev. 2008, 12(4):584-588.
32. Kragl U., VasicRacki D., Wandrey C. Continuous production of l-tert-leucine in series of two enzyme membrane reactors - modelling and computer simulation. Bioprocess Eng. 1996, 14(6):291-297.
33. Landis B.H., McLaughlin J.K., Heeren R., Grabner R.W., Wang P.T. Bioconversion of N-butylglucamine to 6-deoxy-6-butylamino sorbose by Gluconobacter oxydans. Org. Process Res. Dev. 2002, 6(4):547-552.
34. Liang J., Mundorff E., Voladri R., Jenne S., Gilson L., Conway A., Krebber A., Wong J., Huisman G., Truesdell S., Lalonde J. Highly enantioselective reduction of a small heterocyclic ketone: biocatalytic reduction of tetrahydrothiophene-3-one to the corresponding (R)-Alcohol. Org. Process Res. Dev. 2010, 14(1):188-192.
35. Liese A., Seelbach K., Wandrey C. Industrial Biotransformations 2006, John Wiley and Sons Inc. Verlag GmbH & Co kGaA., Weinheim. second ed.
36. Ma S.K., Gruber J., Davis C., Newman L., Gray D., Wang A., Grate J., Huisman G.W., Sheldon R.A. A green-by-design biocatalytic process for atorvastatin intermediate. Green Chem. 2010, 12:81-86.
37. Martínková L., Křen V. Biotransformations with nitrilases. Curr. Opin. Chem. Biol. 2010, 14(2):130-137.
38. Matsumae H., Furui M., Shibatani T. Lipase catalyzed asymmetric hydrolysis of 3-phenylglycidic acid ester, the key intermediate in the synthesis of diltiazem hydrochloride. J. Ferment. Bioeng. 1993, 75:93-98.
39. Nestl B.M., Nebel B.A., Hauer B. Recent progress in industrial biocatalysis. Curr. Opin. Chem. Biol. 2011, 15(2):187-193.
40. Palomares, L.A., Ramírez, O.T., Flickinger, M.C., 2009. Bioreactor scale-up. in: Encyclopedia of Industrial Biotechnology, John Wiley & Sons Inc.
41. Park J.W., Lee J.K., Kwon T.J., Yi D.H., Kim Y.J., Moon S.H., Suh H.H., Kang S.M., Park Y.I. Bioconversion of compactin into pravastatin by Streptomyces sp. Biotechnol. Lett. 2003, 25:1827-1831.
42. Parmar A., Kumar H., Marwaha S.S., Kennedy J.F. Advances in enzymatic transformation of penicillins to 6-aminopenicillanic acid (6-APA). Biotechnol. Adv. 2000, 18:289-301.
43. Patel R.N. Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances. Curr. Opin. Biotechnol. 2001, 12(6):587-604.
44. Patel R.N., Banerjee A., Ko R.Y., Howell J.M., Li W.S., Comezoglu F.T., Partyka R.A., Szarka L.E. Enzymatic preparation of (3R-cis)-3-(acetyloxy)-4-phenyl-2-azetidinone: a taxol side-chain synthon. Biotechnol. Appl. Biochem. 1994, 20:23-33.
45. Patel R.N., Chu L., Chidambaram R., Zhu J., Kant J. Enantioselective microbial reduction of 2-oxo-2-(1'2'3'4'-tetrahydro-1'1'4'4'-tetramethyl-6'-naphthalenyl) acetic acid and its ethyl ester. Tetrahedron-Asymmetry 2002, 13(4):349-355.
46. Patel R.N., Chu L., Mueller R. Diastereoselective microbial reduction of (S)-[3-chloro-2-oxo-1-(phenylmethyl)propyl]carbamic acid, 1,1-dimethylethyl ester. Tetrahedron-Asymmetry 2003, 14(20):3105-3109.
47. Pollard D.J., Woodley J.M. Biocatalysis for pharmaceutical intermediates: the future is now. Trends Biotechnol. 2007, 25(2):66-73.
48. Rao M.B., Tanskale A.P., Ghatge M.S., Deshpande V.V. Molecular and biotechnological aspects of microbial proteases. Microbiol. Mol. Biol. Rev. 1998, 62:597-635.
49. Savage S.A., Jones G.S., Kolotuchin S., Ramrattan S.A., Vu T., Waltermire R.E. Preparation of saxagliptin, a novel DPP-IV inhibitor. Org. Process Res. Dev. 2009, 13(6):1169-1176.
50. Savile, C., Gruber, J., M., Mundoroff, E., Huisman, G.W., Collier, S.J., 2010a. Ketoreductase polypeptides for the production of a 3-aryl-3-hydroxypropanamine from a 3-aryl-3-ketopropanamine. CODEXIS, INC., WO/2010/025238.
51. Savile C.K., Janey J.M., Mundorff E.C., Moore J.C., Tam S., Jarvis W.R., Colbeck J.C., Krebber A., Fleitz F.J., Brands J., Devine P.N., Huisman G.W., Hughes G.J. Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture. Science 2010, 329(5989):305-309.
52. Shafiee A., Motamedi H., King A. Purification, characterization and immobilization of an NADPH-dependent enzyme involved in the chiral specific reduction of the keto ester M, an intermediate in the synthesis of an anti-asthma drug, Montelukast, from Microbacterium campoquemadoensis (MB5614). Appl. Microbiol. Biotechnol. 1998, 49(6):709-717.
53. Sheldon R.A. Chirotechnology 1993, Marcel Dekker Inc., New York.
54. Sheldon R.A. E factors, green chemistry and catalysis: an odyssey. Chem. Commun. 2008, (29):3352-3365.
55. Siegel J.B., Zanghellini A., Lovick H.M., Kiss G., Lambert A.R., Clair J.L., Gallaher J.L., Hilvert D., Gelb M.H., Stoddard B.L., Houk K.N., Michael F.E., Baker D. Computational design of an enzyme catalyst for a stereoselective bimolecular Diels-Alder reaction. Science 2010, 329(5989):309-313.
56. Stuermer R., Hauer B., Hall M., Faber K. Asymmetric bioreduction of activated CC bonds using enoate reductases from the old yellow enzyme family. Curr. Opin. Chem. Biol. 2007, 11(2):203-213.
57. Tao J., Kazlaukas R.J. Biocatalysis Fro Green Chemistry and Chemical Process Development 2011, John Wiley & Sons Ltd., Hoboken, New Jersey.
58. Tufvesson P., Fu W., Jensen J.S., Woodley J.M. Process considerations for the scale-up and implementation of biocatalysis. Food Bioprod. Process 2010, 88(1):3-11.
59. Vrtis J.M., White A.K., Metcalf W.W., van der Donk W.A. Phosphite dehydrogenase: a versatile cofactor-regeneration enzyme. Angew. Chem.Int. Ed. Engl. 2002, 41(17):3257-3259.
60. Walsgrove T.C., Powell L., Wells A. Lotrafiban, [(2S)-7-(4,4'-bipiperidinylcarbonyl)-2,3,4,5,-tetrahydro-4-methyl-4-oxo-1H-1, 4-benzodiazepine-2-acetic acid] utilising an enzymatic resolution as the final step. Org. Process Res. Dev. 2002, 6:488-491.
61. Wong J.W., Watson H.A., Bouressa J.F., Burns M.P., Cawley J.J., Doro A.E., Guzek D.B., Hintz M.A., McCormick E.L., Scully D.A., Siderewicz J.M., Taylor W.J., Truesdell S.J., Wax R.G. Biocatalytic oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. Org. Process Res. Dev. 2002, 6:477-481.
62. Yoshikawa N., Ohta K., Mizuno S., Ohkishi H. Production of cis,cis-muconic acid from benzoic acid. Bioprocess Technol. 1993, 16:131-147.
63. Zhang Y., Gao F., Zhang S.P., Su Z.G., Ma G.H., Wang P. Simultaneous production of 1,3-dihydroxyacetone and xylitol from glycerol and xylose using a nanoparticle-supported multi-enzyme system with in situ cofactor regeneration. Bioresour. Technol. 2011, 102(2):1837-1843.