Chemical and enzymatic approaches to the synthesis of optically pure ethyl (R)-4-cyano-3-hydroxybutanoate

Applied Microbiology and Biotechnology

Volumn 98, Issue 1, 2014, Pages 11-21

  You, Zhong Yu ^a   Liu, Zhi Qiang ^a   Zheng, Yu Guo ^a  

^a ZHEJIANG UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Chemical synthesis; Enzymatic synthesis; Ethyl (R) 4 cyano 3 hydroxybutanoate; Synthetic approach

Indexed keywords

BIOLOGY; BIOTECHNOLOGY; SYNTHESIS (CHEMICAL);

CHOLESTEROL LOWERING; ENZYMATIC SYNTHESIS; ETHYL (R)-4-CYANO-3-HYDROXYBUTANOATE; HALOHYDRIN DEHALOGENASE; HYDROXYMETHYLGLUTARYL; REDUCTASE INHIBITORS; SYNTHETIC APPROACH; SYNTHETIC STRATEGIES;

STEREOCHEMISTRY;

BUTYRIC ACID; CARBONYL REDUCTASE; ENZYME; EPICHLOROHYDRIN; ETHYL 4 CYANO 3 HYDROXYBUTANOATE; HALOHYDRIN DEHALOGENASE; MALIC ACID; MALTODEXTRIN; NITRILASE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

AMINO ACID; DRUG; DRUG DEVELOPMENT; ENZYME ACTIVITY; OPTICAL METHOD;

BIOCATALYST; NONHUMAN; REVIEW; SYNTHESIS;

BIOTECHNOLOGY; CHEMISTRY; ENZYMES; HYDROXYBUTYRATES;

EID: 84891847972     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-5357-0     Document Type: Review

References (98)

1. Anastas P, Eghbali N (2010) Green chemistry: principles and practice. Chem Soc Rev 39:301-312
2. Archelas A, Furstoss R (1997) Synthesis of enantiopure epoxides through biocatalytic approaches. Annu Rev Microbiol 51:491-525
3. Asako H, Shimizu M, Itoh N (2009) Biocatalytic production of (S)-4-bromo-3-hydroxybutyrate and structurally related chemicals and their applications. Appl Microbiol Biotechnol 84:397-405
4. Barrios-Gonzalez J, Miranda RU (2010) Biotechnological production and applications of statins. Appl Microbiol Biotechnol 85:869-883
5. Bergeron S, Chaplin DA, Edwards JH, Ellis BSW, Hill CL, Holt-Tiffin K, Knight JR, Mahoney T, Osborne AP, Ruecroft G (2006) Nitrilase-catalysed desymmetrisation of 3-hydroxyglutaronitrile: preparation of a statin side-chain intermediate. Org Process Res Dev 10:661-665
6. Bhushan I, Kumar A, Modi G, Jamwal S (2011) Chiral resolution of differently substituted racemic acetyl-1-phenyl ethanol using lipase from Bacillus subtilis. J Chem Technol Biotechnol 86:315-318
7. Bornscheuer UT, Kazlauskas RJ (1999) Hydrolases in organic synthesis - region- and stereoselective biotransformations. Wiley, Weinheim
8. Bottcher D, Bornscheuer UT (2010) Protein engineering of microbial enzymes. Curr Opin Microbiol 13:274-282
9. Brooks WH, Guida WC, Daniel KG (2011) The significance of chirality in drug design and development. Curr Top Med Chem 11:760-770
10. Brower PL, Butler DE, Deering CF, Le TV, Millar A, Nanninga TN, Roth BD (1992) The synthesis of (4r-Cis)-1,1-dimethylethyl 6-cyanomethyl-2,2-dimethyl-1, 3-dioxane-4-acetate, a key intermediate for the preparation of Ci-981, a highly potent, tissue selective inhibitor of Hmg-Coa reductase. Tetrahedron Lett 33:2279-2282
11. Burk MJ, DeSantis G, Morgan G, Zhu ZL (2011) Process for making (R)-ethyl 4-cyano-3 hydroxybutyric acid, US 7932064B2
12. Candela M, Ruiz A, Feo FJ (2000) Validation of an analysis method for 4-amino-3-hydroxybutyric acid by reversed-phase liquid chromatography. J Chromatogr A 890:273-280
13. Chauhan S, Wu S, Blumerman S, Fallon RD, Gavagan JE, DiCosimo R, Payne MS (2003) Purification, cloning, sequencing and over-expression in Escherichia coli of a regioselective aliphatic nitrilase from Acidovorax facilis 72W. Appl Microbiol Biotechnol 61:118-122
14. Chen J, Zheng YG, Shen YC (2008) Biotransformation of p-methoxyphenylacetonitrile into p-methoxyphenylacetic acid by resting cells of Bacillus subtilis. Biotechnol Appl Biochem 50:147-153
15. Chen J, Zheng RC, Zheng YG, Shen YC (2009) Microbial transformation of nitriles to high-value acids or amides. Adv Biochem Eng Biotechnol 113:33-77
16. Davis SC, Grate JH, Gray DR, Gruber JM, Huisman GW, Ma SK, Newman LM, Sheldon R, Wang LA (2004) Enzymatic processes for the production of 4-substituted 3-hydroxybutyric acid derivatives. WO2004015132A2
17. Davis SC, Grate JH, Gray DR, Gruber JM, Huisman GW, Ma SK, Newman LM, Sheldon R, Wang LA (2006) Enzymatic processes for the production of 4-substituted 3-hydroxybutyric acid derivatives and vicinal cyano, hydroxy substituted carboxylic acid esters. WO 2004015132A2
18. de Jong RM, Tiesinga JJW, Rozeboom HJ, Kalk KH, Tang L, Janssen DB, Dijkstra BW (2003) Structure and mechanism of a bacterial haloalcohol dehalogenase: a new variation of the short-chain dehydrogenase/reductase fold without an NAD(P)H binding site. Embo J 22:4933-4944
19. de Jong RM, Tiesinga JJW, Villa A, Tang LX, Janssen DB, Dijkstra BW (2005) Structural basis for the enantioselectivity of an epoxide ring opening reaction catalyzed by halo alcohol dehalogenase HheC. J Am Chem Soc 127:13338-13343
20. DeSantis G, Zhu ZL, Greenberg WA, Wong KV, Chaplin J, Hanson SR, Farwell B, Nicholson LW, Rand CL, Weiner DP, Robertson DE, Burk MJ (2002) An enzyme library approach to biocatalysis: development of nitrilases for enantioselective production of carboxylic acid derivatives. J Am Chem Soc 124:9024-9025
21. DeSantis G, Wong K, Farwell B, Chatman K, Zhu ZL, Tomlinson G, Huang HJ, Tan XQ, Bibbs L, Chen P, Kretz K, Burk MJ (2003) Creation of a productive, highly enantioselective nitrilase through gene site saturation mutagenesis (GSSM). J Am Chem Soc 125:11476-11477
22. Findrik Z, Vasic-Racki D (2009) Overview on reactions with multi-enzyme systems. Chem Biochem Eng Q 23:545-553
23. Fox RJ, Davis SC, Mundorff EC, Newman LM, Gavrilovic V, Ma SK, Chung LM, Ching C, Tam S, Muley S, Grate J, Gruber J, Whitman JC, Sheldon RA, Huisman GW (2007) Improving catalytic function by ProSAR-driven enzyme evolution. Nat Biotechnol 25:338-344
24. Garrett RL (1996) Pollution prevention, green chemistry, and the design of safer chemicals. In: Devito SC, Garrett RL (eds) Designing safer chemicals green chemistry for pollution prevention, vol 640. American Chemical Society, Washington, pp 2-15
25. Guercio G, Manzo AM, Goodyear M, Bacchi S, Curti S, Provera S (2009) Synthesis of the NK1 receptor antagonist GW597599. Part 2: development of a scalable route to a key chirally pure arylpiperazine. Org Process Res Dev 13:489-493
26. Hasan F, Shah AA, Hameed A (2006) Industrial applications of microbial lipases. Enzym Microb Technol 39:235-251
27. He CM, Chang DL, Zhang J (2008a) Asymmetric reduction of substituted α- and β-ketoesters by Bacillus pumilus Phe-C3. Tetrahedron-Asymmetry 19:1347-1351
28. He F, Pan QH, Shi Y, Duan CQ (2008b) Chemical synthesis of proanthocyanidins in vitro and their reactions in aging wines. Molecules 13:3007-3032
29. Hoff BH, Anthonsen T (1999) Lipase-catalyzed resolution of esters of 4-chloro-3-hydroxybutanoic acid: effects of the alkoxy group and solvent on the enantiomeric ratio. Tetrahedron-Asymmetry 10:1401-1412
30. Hoffmann F, Maser E (2007) Carbonyl reductases and pluripotent hydroxysteroid dehydrogenases of the shortchain dehydrogenase/reductase superfamily. Drug Metab Rev 39:87-144
31. Hong HB, Jiang CJ (2009) Preparation of ethyl (R)-(-)-4-cyano-3- hydroxybutyrate. Chin J Pharm 40:486-487
32. Houde A, Kademi A, Leblanc D (2004) Lipases and their industrial applications - an overview. Appl Biochem Biotechnol 118:155-170
33. Humble MS, Berglund P (2011) Biocatalytic promiscuity. Eur J Org Chem 2011:3391-3401
34. Hutt AJ, O'Grady J (1996) Drug chirality: a consideration of the significance of the stereochemistry of antimicrobial agents. J Antimicrob Chemother 37:7-32
35. Hwang SO, Chung SH (2009) Method of making optically active ester derivatives and their acids from racemic esters. US7485452B2
36. Inoue K, Makino Y, Dairi T, Itoh N (2006) Gene cloning and expression of Leifsonia alcohol dehydrogenase (LSADH) involved in asymmetric hydrogen-transfer bioreduction to produce (R)-form chiral alcohols. Biosci Biotechnol Biochem 70:418-426
37. Janssen DB, Majeric-Elenkov M, Hasnaoui G, Hauer B, Lutje Spelberg JH (2006) Enantioselective formation and ring-opening of epoxides catalysed by halohydrin dehalogenases. Biochem Soc Trans 34:291-295
38. Jiang CJ, Hong HB (2012) A new practical synthesis of ethyl (R)-(-)-4-cyano-3-hydroxybutyrate from (S)-3-chloro-1,2-propanediol. Lett Org Chem 9:520-521
39. Jiang SD, Singh G (1998) Chemical synthesis of shikimic acid and its analogues. Tetrahedron 54:4697-4753
40. Jin J, Zhang J (2012) Enzymatic synthesis of both enantiomers of ethyl 4-cyano-3-hydroxybutanoate. Adv Mater Res 343-344:448-452
41. Jin LQ, Li YF, Liu ZQ, Zheng YG, Shen YC (2011) Characterization of a newly isolated strain Rhodococcus erythropolis ZJB-09149 transforming 2-chloro-3-cyanopyridine to 2-chloronicotinic acid. New Biotechnol 28:610-615
42. Jung H, Jung K, Kleber HP (1993) Synthesis of L-carnitine by microorganisms and isolated enzymes. Adv Biochem Eng Biotechnol 50:21-44
43. Kakeya H, Sakai N, Sugai T, Ohta H (1991) Microbial hydrolysis as a potent method for the preparation of optically-active nitriles, amides and carboxylic-acids. Tetrahedron Lett 32:1343-1346
44. Kataoka M, Kita K, Wada M, Yasohara Y, Hasegawa J, Shimizu S (2003) Novel bioreduction system for the production of chiral alcohols. Appl Microbiol Biotechnol 62:437-445
45. Kaul P, Banerjee A, Mayilraj S, Banerjee UC (2004) Screening for enantioselective nitrilases: kinetic resolution of racemic mandelonitrile to (R)-(-)-mandelic acid by new bacterial isolates. Tetrahedron-Asymmetry 15:207-211
46. Kita K, Kataoka M, Shimizu S (1999) Diversity of 4-chloroacetoacetate ethyl ester-reducing enzymes in yeasts and their application to chiral alcohol synthesis. J Biosci Bioeng 88:591-598
47. Kizaki N, Yasohara Y, Hasegawa J, Wada M, Kataoka M, Shimizu S (2001) 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 55:590-595
48. Kumar P, Deshmukh AN, Upadhyay RK, Gurjar MK (2005) A simple and practical approach to enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone: synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester. Tetrahedron- Asymmetry 16:2717-2721
49. Leonida MD (2001) Redox enzymes used in chiral syntheses coupled to coenzyme regeneration. Curr Med Chem 8:345-369
50. Lespieau R (1923) Nitriles β-oxyglutarique, β-bromoglutarique et gultaconique. Bull Soc Chim Fr 33:725-733
51. Liu ZQ, Dong LZ, Cheng F, Xue YP, Wang YS, Ding JN, Zheng YG, Shen YC (2011a) Gene cloning, expression, and characterization of a nitrilase from Alcaligenes faecalis ZJUTB10. J Agric Food Chem 59:11560-11570
52. Liu ZQ, Li FF, Cheng F, Zhang T, You ZY, Xu JM, Xue YP, Zheng YG, Shen YC (2011b) A novel synthesis of iminodiacetic acid: biocatalysis by whole Alcaligenes faecalis ZJB-09133 cells from iminodiacetonitrile. Biotechnol Prog 27:698-705
53. Liu ZQ, Zhang LP, Cheng F, Ruan LT, Hu ZC, Zheng YG, Shen YC (2011c) Characterization of a newly synthesized epoxide hydrolase and its application in racemic resolution of (R, S)-epichlorohydrin. Catal Commun 16:133-139
54. Liu ZQ, Zheng XB, Zhang SP, Zheng YG (2012a) Cloning, expression and characterization of a lipase gene from the Candida antarctica ZJB09193 and its application in biosynthesis of vitamin A esters. Microbiol Res 167:452-460
55. Liu ZQ, Zhou M, Zhang XH, Xu JM, Xue YP, Zheng YG (2012b) Biosynthesis of iminodiacetic acid from iminodiacetonitrile by immobilized recombinant Escherichia coli harboring nitrilase. J Mol Microbiol Biotechnol 22:35-47
56. Lunzer R, Ortner I, Haltrich D, Kulbe KD, Nidetzky B (1998) Enzymatic regeneration of NAD in enantioselective oxidation of secondary alcohols: glutamate dehydrogenase versus NADH dehydrogenase. Biocatal Biotransform 16:333-349
57. Lv SX, Guo YH, Wang YP, Wang XJ, Xiang WS (2009) A novel synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester. Chin J Org Chem 29:1997-1999
58. Ma SK, Gruber J, Davis C, Newman L, Gray D, Wang A, Grate J, Huisman GW, Sheldon RA (2010) A green-by-design biocatalytic process for atorvastatin intermediate. Green Chem 12:81-86
59. Majerić Elenkov M, Hauer B, Janssen DB (2006) Enantioselective ring opening of epoxides with cyanide catalysed by halohydrin dehalogenases: a new approach to non-racemic β-hydroxy nitriles. Adv Synth Catal 348:579-585
60. Majeric Elenkov M, Tang L, Hauer B, Janssen DB (2006) Sequential kinetic resolution catalyzed by halohydrin dehalogenase. Org Lett 8:4227-4229
61. Matsuda H, Shibata T, Hashimoto H, Kitai M (1999) Method for producing (R)-4-cyano-3-hydroxybutyric acid lower alkyl ester. US5908953
62. Mete E, Maras A, Secen H (2003) A short synthesis of 4-amino-3- hydroxybutyric acid (GABOB) via allyl cyanide. Russ Chem B+ 52:1879-1881
63. Mitsuhashi S, Sakurai K, Kumobayashi H (1995) T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate and process for preparing the same. US5430171
64. Moen AR, Hoff BH, Hansen LK, Anthonsen T, Jacobsen EE (2004) Absolute configurations of monoesters produced by enzyme catalyzed hydrolysis of diethyl 3-hydroxyglutarate. Tetrahedron-Asymmetry 15:1551-1554
65. Narina SV, Sudalai A (2007) Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines. Tetrahedron 63:3026-3030
66. Nguyena LA, Hua H, Chuong P-H (2006) Chiral drugs: an overview. Int J Biomed Sci 2:85-100
67. Okano K, Tokuyama H, Fukuyama T (2008) Total synthesis of (+)-yatakemycin. Chem-Asian J 3:296-309
68. Pantaleone DP (2005) Biotransformations: green processes for the synthesis of chiral fine chemicals. In: Ager DJ (ed) Handbook of chiral chemicals. CRC, New York, pp 359-403
69. Patel RN (2006) Biocatalysis: synthesis of chiral intermediates for drugs. Curr Opin Drug Discov Dev 9:741-764
70. Patel RN (2008) Synthesis of chiral pharmaceutical intermediates by biocatalysis. Coord Chem Rev 252:659-701
71. Patel JM (2009) Biocatalytic synthesis of atorvastatin intermediates. J Mol Catal B Enzym 61:123-128
72. Presecki AV, Vasic-Racki D (2009) Mathematical modelling of the dehydrogenase catalyzed hexanol oxidation with coenzyme regeneration by NADH oxidase. Process Biochem 44:54-61
73. Rajesh T, Madhusudhan G, Mukkanti K, Narayana Rao SP, Kishore Babu K (2011) A new and concise synthetic route to enantiopure Linezolid from (S)-epichlorohydrin. Der Pharma Chem 3:168-175
74. Robertson DE, Chaplin JA, DeSantis G, Podar M, Madden M, Chi E, Richardson T, Milan A, Miller M, Weiner DP, Wong K, McQuaid J, Farwell B, Preston LA, Tan XQ, Snead MA, Keller M, Mathur E, Kretz PL, Burk MJ, Short JM (2004) Exploring nitrilase sequence space for enantioselective catalysis. Appl Environ Microbiol 70:2429-2436
75. Roh KR, Yu HS, Kim KI, Lee WJ, Hwang DI (2003) Process for preparing (R)-4-cyano-3-hydroxybutyric acid ester. US6586616B1
76. Romeo G, Chiacchio U, Corsaro A, Merino P (2010) Chemical synthesis of heterocyclic-sugar nucleoside analogues. Chem Rev 110:3337-3370
77. Roth BD. (1987) Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl) alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthsis, US4681893
78. Roth BD (2002) The discovery and development of atorvastatin, a potent novel hypolipidemic agent. Prog Med Chem 40:1-22
79. Schallmey M, Floor RJ, Hauer B, Breuer M, Jekel PA, Wijma HJ, Dijkstra BW, Janssen DB (2013) Biocatalytic and structural properties of a highly engineered halohydrin dehalogenase. ChemBioChem 14:870-881
80. Shen M, Zheng YG, Liu ZQ, Shen YC (2009) Production of acrylic acid from acrylonitrile by immobilization of Arthrobacter nitroguajacolicus ZJUTB06-99. J Microbiol Biotechnol 19:582-587
81. Sundby E, De Zotti M, Anthonsen T (2003) The enantioselectivity of reduction of ethyl 4-halo-3-oxobutanoate catalyzed by Geotrichum candidum depends on the cofactor. J Mol Catal B Enzym 21:63-66
82. Tang LX, van Hylckama JET, Spelberg JHL, Fraaije MW, Janssen DB (2002) Improved stability of halohydrin dehalogenase from Agrobacterium radiobacter AD1 by replacement of cysteine residues. Enzym Microb Technol 30:251-258
83. Tang LX, Spelberg JHL, Fraaije MW, Janssen DB (2003) Kinetic mechanism and enantioselectivity of halohydrin dehalogenase from Agrobacterium radiobacter. Biochemistry 42:5378-5386
84. Tang LX, Pazmino DET, Fraaije MW, de Jong RM, Dijkstra BW, Janssen DB (2005) Improved catalytic properties of halohydrin dehalogenase by modification of the halide-binding site. Biochemistry 44:6609-6618
85. Tao J, Xu JH (2009) Biocatalysis in development of green pharmaceutical processes. Curr Opin Chem Biol 13:43-50
86. Turner NJ (2009) Directed evolution drives the next generation of biocatalysts. Nat Chem Biol 5:568-574
87. Uppenberg J, Hansen MT, Patkar S, Jones TA (1994) The sequence, crystal structure determination and refinement of two crystal forms of lipase B from Candida antarctica. Structure 2:293-308
88. van den Wijngaard AJ, Reuvekamp PT, Janssen DB (1991) Purification and characterization of haloalcohol dehalogenase from Arthrobacter sp. strain AD2. J Bacteriol 173:124-129
89. van Hylckama Vlieg JE, Tang L, Lutje Spelberg JH, Smilda T, Poelarends GJ, Bosma T, van Merode AE, Fraaije MW, Janssen DB (2001) Halohydrin dehalogenases are structurally and mechanistically related to short-chain dehydrogenases/reductases. J Bacteriol 183:5058-5066
90. Wakita R (2004) Method for producing 4-cyano-3-oxobutanoate and 4-cyano-3-hydroxybutanoate. US6781009B2
91. Wang GJ, Hollingsworth RI (1999) Synthetic routes to L-carnitine and L-gamma-amino-beta-hydroxybutyric acid from (S)-3-hydroxybutyrolactone by functional group priority switching. Tetrahedron-Asymmetry 10:1895-1901
92. Wang LJ, Li CX, Ni Y, Zhang J, Liu X, Xu JH (2011) Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor. Bioresour Technol 102:7023-7028
93. Xue YP, Xu SZ, Liu ZQ, Zheng YG, Shen YC (2011) Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(-)-mandelic acid by a newly isolated mutant strain. J Ind Microbiol Biotechnol 38:337-345
94. Yamamoto K, Ueno Y, Otsubo K, Kawakami K, Komatsu KI (1990) Production of S-(+)-Ibuprofen from a nitrile compound by Acinetobacter sp strain-Ak226. Appl Environ Microbiol 56:3125-3129
95. Ye Q, Ouyang P, Ying H (2011) A review-biosynthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate ester: recent advances and future perspectives. Appl Microbiol Biotechnol 89:513-522
96. You ZY, Liu ZQ, Zheng YG (2013a) Characterization of a newly synthesized carbonyl reductase and construction of a biocatalytic process for the synthesis of ethyl (S)-4-chloro-3-hydroxybutanoate with high space-time yield. Appl Microbiol Biotechnol. doi: 10.1007/s00253-013-5042-3
97. You ZY, Liu ZQ, Zheng YG (2013b) Properties and biotechnological applications of halohydrin dehalogenases: current state and future perspectives. Appl Microbiol Biotechnol 97:9-21
98. Zhu DM, Mukherjee C, Hua L (2005) 'Green' synthesis of important pharmaceutical building blocks: enzymatic access to enantiomerically pure alpha-chloroalcohols. Tetrahedron-Asymmetry 16:3275-3278