Uses and production of chiral 3-hydroxy-γ-butyrolactones and structurally related chemicals

Applied Microbiology and Biotechnology

Volumn 84, Issue 5, 2009, Pages 817-828

  Lee, Sang Hyun ^a   Park, Oh Jin ^a,b  

^a LG Chemical Ltd   (South Korea)

^b Canada Institute of Linguistics   (Canada)

Author keywords

(S) 3 hydroxy butyrolactone; Biocatalysis; Chiral; Enzymatic; Hydrogenation; Statin

Indexed keywords

3-HYDROXYBUTYRATE; BIOCATALYSIS; BIOLOGICAL METHODS; BUTYROLACTONES; CHEMICAL METHOD; CHIRAL; CHIRAL BUILDING BLOCKS; ENANTIOPURE; ENZYMATIC; MALIC ACIDS; OPTICALLY ACTIVE; RECOMBINANT MICROORGANISM; RELATED COMPOUNDS; SELECTIVE HYDROGENATION; STARTING MATERIALS; STATIN; STATINS; SYNTHETIC APPLICATION; SYNTHETIC ORGANIC CHEMISTRY; SYNTHETIC ROUTES; UNIT PROCESS;

BIOMASS; CARBOHYDRATES; CATALYSTS; ENZYMES; MICROORGANISMS; ORGANIC CHEMICALS; SYNTHESIS (CHEMICAL);

HYDROGENATION;

3 HYDROXY GAMMA BUTYROLACTONE DERIVATIVE; 4 CHLORO 3 HYDROXYBUTYRATE; AMIDASE; BUTYROLACTONE; HYDROXYBUTYRIC ACID; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; HYDROXYNITRILE LYASE; NITRILE HYDRATASE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

BIOMASS; CATALYSIS;

CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME DEGRADATION; ENZYME SYNTHESIS; NONHUMAN; SHORT SURVEY; SYNTHESIS;

4-BUTYROLACTONE; BIOCATALYSIS; CHEMISTRY, ORGANIC; ENZYMES; INDUSTRIAL MICROBIOLOGY;

EID: 70349255546     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-009-2143-0     Document Type: Short Survey

References (69)

1. S Bergeron DA Chaplin JH Edwards BSW Ellis CL Hill K Holt-Tiffin JR Knight T Mahoney AP Osborne G Ruecroft 2006 Nitrilase-catalyzed desymmetrization of 3-hydroxyglutaronitrile: preparation of a statin side-chain intermediate Org Process Res Dev 10 661 665
2. Byun IS, Kim KI, Bong CA (2002) Process for the preparation of l-carnitine. US patent no. 6,342,034
3. M Chartrain R Greasham J Moore P Reider D Robinson B Buckland 2001 Asymmetric bioreductions: application to the synthesis of pharmaceuticals J Mol Catal B Enzym 11 503 512
4. Y Chikusa Y Hirayama M Ikunaka T Inoue S Kamiyama M Moriwaki Y Nishimoto F Nomoto K Ogawa T Ohno K Otsuka AK Sakota N Shirasaka A Uzura K Uzura 2003 There's no industrial biocatalyst like hydrolase: development of scalable enantioselective processes using hydrolytic enzymes Org Process Res Dev 7 289 296
5. YH Choi KN Uhm HK Kim 2008 Biochemical characterization of Rhodococcus erythropolis no. 4 nitrile hydratase acting on 4-chloro-3-hydroxybutyronitrile J Mol Catal B Enzym 55 157 163
6. WJ Choi SM Puah LL Tan SS Ng 2008 Production of (R)-ethyl-3,4- epoxybutyrate by newly isolated Acinetobacter baumannii containing epoxide hydrolase Appl Microbiol Biotechnol 79 61 67
7. SMA De Wildeman T Sonke HE Schoemaker O May 2007 Biocatalytic reductions: from lab curiosity to first choice Acc Chem Res 40 1260 1266
8. G Desantis K Wong B Farwell K Chatman Z Zhu G Tomlinson H Huang X Tan L Bibbs P Chen K Kretz MJ Burk 2003 Creation of a productive, highly enantioselective nitrilase through gene site saturation mutagenesis (GSSM) J Am Chem Soc 125 11476 11477
9. JR Ella-Meyne G Wang 2007 Synthesis of chiral 2-oxazolidinones, 2-oxazolines, and their analogs Tetrahedron 73 10034 10041
10. RJ Fox SC Davis EC Mundorff LM Newman V Gavrilovic SK Ma LM Chung C Ching S Tam S Muley J Grate J Gruber JC Whitman RA Sheldon GW Huisman 2007 Improving catalytic function by ProSAR-driven enzyme evolution Nat Biotechnol 25 338 344
11. ME Furrow SE Schaus EN Jacobsen 1998 Practical access to highly enantioenriched C-3 building blocks via hydrolytic kinetic resolution J Org Chem 63 6776 6777
12. Furukawa Y, Shiomi Y, Nagao K (1996) Improved process for producing 4-hydroxy-2-pyrrolidone. WO patent 1996/036603
13. K Goldberg K Schroer S Lütz A Liese 2007 Biocatalytic ketone reduction-a powerful tool for the production of chiral alcohols-part I: processes with isolated enzymes Appl Microbiol Biotechnol 76 237 248
14. K Goldberg K Schroer S Lütz A Liese 2007 Biocatalytic ketone reduction-a powerful tool for the production of chiral alcohols-part II: whole-cell reductions Appl Microbiol Biotechnol 76 249 255
15. WA Greenberg A Varvak SR Hanson K Wong H Huang P Chen MJ Burk 2004 Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates Proc Nat Acad Sci U S A 101 5788 5793
16. J Hasegawa S Hamaguchi M Ogura K Watanabe 1981 Production of β-hydroxycarboxylic acids from aliphatic carboxylic acids by microorganisms J Ferment Technol 59 57 262
17. RI Hollingsworth 1999 Taming carbohydrate complexity: a facile, high-yield route to chiral 2,3-dihydroxybutanoic acids and 4- hydroxytetrahydrofuran-2-ones with very high optical purity from pentose sugars J Org Chem 64 7633 7634
18. Hollingsworth RI (2001) Process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom. US patent no. 6,239,311
19. RI Hollingsworth G Wang 2000 Toward a carbohydrate-based chemistry: progress in the development of general-purpose chiral synthons from carbohydrates Chem Rev 100 4267 4282
20. Hwang SO, Chung SH (2007) The method of making optically active 3-acyloxy-γ-butyrolactone and optically active 3-hydroxy-γ- hydroxybutyrolactone by enzymatic method. WO patent 2007/035066
21. Hwang SO, Chung SH (2008) Process for the preparation of l-carnitine. Korea patent 10-0846673
22. Hwang SO, Chung SH (2009) Method of making optically active ester derivatives and their acids from their racemic esters. US patent no. 7,485,452
23. Hwang SO, Ryu HY, Chung SH, Lee TI (2007) The method of making optically active 3-hydroxy-γ-butyrolactone by enzymatic method. Korea patent 10-0657204
24. M Ikunaka 2004 Biocatalysis from the perspective of an industrial practitioner: let a biocatalyst do a job that no chemocatalyst can Catal Today 96 93 102
25. S Jennewein M Schürmann HI WolbergM R Luiten M Wubbolts D Mink 2006 Directed evolution of an industrial biocatalyst: 2-deoxy-d-ribose 5-phosphate aldolase J Biotechnol 1 537 548
26. N Kasai T Suzuki 2003 Industrialization of the microbial resolution of chiral C3 and C4 synthetic unit: from a small beginning to a major operation, a personal account Adv Synth Catal 345 437 455
27. M Kataoka K Kita M Wada Y Yasohara J Hasegawa S Shimizu 2003 Novel bioreduction system for the production of chiral alcohols Appl Microbiol Biotechnol 62 437 445
28. Kazumasa H, Yoshiro F, Shigeo K, Yoshikazu T (2001) Process of producing 3-hydroxy-γ-butyrolactone derivatives. US patent no. 6,268,515
29. EE Kim CT Baker MD Dwyer MA Murcko BG Rao RD Tung MA Navia 1995 Crystal structure of HIV-1 protease in complex with VX-478, a potent and orally bioavailable inhibitor of the enzyme J Am Chem Soc 117 1181 1182
30. P Kumar AN Deshmukh RK Upadhyay MK Gurjar 2005 A simple and practical approach to enantiomerically pure (S)-3-hydroxy-γ-butyrolactone: synthesis of (R)-4-cyano-3-hydroxybutyric acid ethyl ester Tetrahedron Asymmetry 16 2717 2727
31. BS Kwak 2003 Development of chiral pharmaceutical fine chemicals through technology fusion Chim Oggi 21 23 26
32. SY Lee Y Lee F Wang 1999 Chiral compounds from bacterial polyesters: sugars to plastics to fine chemicals Biotechnol Bioeng 65 363 368
33. SH Lee OJ Park HS Uh 2008 A chemoenzymatic approach to the synthesis of enantiomerically pure (S)-3-hydroxy-γ-butyrolactone Appl Microbiol Biotechnol 79 355 362
34. SH Lee SJ Park SY Lee SH Hong 2008 Biosynthesis of enantiopure (S)-3-hydroxybutyric acid in metabolically engineered Escherichia coli Appl Microbiol Biotechnol 79 633 641
35. JE Leresche H-P Meyer 2006 Chemocatalysis and biocatalysis (biotransformation): some thoughts of a chemist and of a biotechnologist Org Process Res Dev 10 572 580
36. Q Liu SP Ouyang A Chung Q Wu GQ Chen 2007 Microbial production of R-3-hydroxybutyric acid by recombinant E. coli harboring genes of phbA, phbB, and tesB Appl Microbiol Biotechnol 76 811 818
37. CH Martin KLJ Prather 2008 High-titer production of monomeric hydroxyvalerates from levulinic acid in Pseudomonas putida J Biotechnol 139 61 67
38. T Matsuda R Yamanaka K Nakamura 2009 Recent progress in biocatalysis for asymmetric oxidation and reduction Tetrahedron Asymmetry 20 513 557
39. A Matsuyama H Yamamoto Y Kobayashi 2002 Practical application of recombinant whole-cell biocatalysts for the manufacturing of pharmaceutical intermediates such as chiral alcohols Org Process Res Dev 6 558 561
40. Mitsuhashi S, Kumobayashi H (1998) Process for preparing optically active 4-hydroxy-2-pyrrolidone. US patent no. 5,837,877
41. JC Moore DJ Pollard B Kosjek PN Devine 2007 Advances in the enzymatic reduction of ketones Acc Chem Res 40 1412 1419
42. M Müller 2005 Chemoenzymatic synthesis of building blocks of statin side chains Angew Chem Int Ed 44 362 365
43. A Nakagawa J Idogaki K Kato A Shinmyo T Suzuki 2006 Improvement on production of (R)-4-chloro-3-hydroxybutyrate and (S)-3-hydroxy-γ- butyrolactone with recombinant Escherichia coli cells J Biosci Bioeng 101 97 103
44. A Nakagawa K Kato A Shinmyo T Suzuki 2007 Asymmetric hydrolysis of 2-hydroxy-carboxylic esters using recombinant Escherichia coli Tetrahedron Asymmetry 18 2394 2398
45. A Nakagawa T Suzuki K Kato A Shinmyo T Suzuki 2008 Production of (S)-4-chloro-3-hydroxybutyrate by microbial resolution using hydrolase from Rhizobium sp. DS-S-51 J Biosci Bioeng 105 313 318
46. National Renewable Energy Laboratory (2004) In: Werpy T, Peterson G (eds) Top value added chemicals from biomass, vol. 1. Results of screening for potential candidates from sugars and synthesis gas. Technical report
47. Nishikawa M (2000) Method of producing 4-hydroxy-2-pyrrolidinone and method of purifying the same. US patent no. 6,153,766
48. Park YM, Chun JP, Rho KR Yu HS, Hwang I (2004) Process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone. US patent no. 6,713,290
49. OJ Park SH Lee TY Park WG Chung SH Lee 2006 Development of a scalable process for a key intermediate of (R)-metalaxyl by enzymatic kinetic resolution Org Process Res Dev 10 588 591
50. HJ Park KN Uhm HK Kim 2008 R-stereoselective amidase from Rhodococcus erythropolis No. 7 acting on 4-chloro-3-hydroxybutyramide J Microbiol Biotechnol 18 552 559
51. RN Patel 2008 Synthesis of chiral pharmaceutical intermediates by biocatalysis Coord Chem Rev 252 659 701
52. B Pscheidt A Glieder 2008 Yeast cell factories for fine chemical and API production Microb Cell Fact 7 25
53. N Ran L Zhao Z Chen J Tao 2008 Recent applications of biocatalysis in developing green chemistry for chemical synthesis at the industrial scale Green Chem 10 361 372
54. N Ran E Lui J Liu J Tao 2009 Chemoenzymatic synthesis of small molecule human therapeutics Curr Pharm Des 15 134 152
55. BE Rossiter KB Sharpless 1984 Asymmetric epoxidation of homoallylic alcohols. Synthesis of (-)-γ-amino-beta (R)-hydroxybutyric acid (GABOB) J Org Chem 49 3707 3711
56. AM Rouhi 2003 Custom chemicals Chem Eng News 81 7 55 73
57. SE Schaus BD Brandes JF Larrow M Tokunaga KB Hansen AE Gould ME Furrow EN Jacobsen 2002 Highly selective hydrolytic kinetic resolution of terminal epoxides catalyzed by chiral (salen) CoIII complexes. Practical synthesis of enantioenriched terminal epoxides and 1,2-diols J Am Chem Soc 124 1307 1315
58. Shin HI, Chang JH, Woo YM, Kim YS (2005) A process for the synthesis of 3-hydroxy-gamma-butyrolactone. WO patent 2005/030747
59. T Suzuki H Idogaki N Kasai 1999 Dual production of highly pure methyl (R)-4-chloro-3-hydroxybutyrate and (S)-3-hydroxy-gamma-butyrolactone with Enterobacter sp Enzyme Microb Technol 24 13 20
60. AM Thayer 2006 Competitors want to get a piece of Lipitor Chem Eng News 84 26 27
61. HC Tseng CH Martin DR Nielsen KL Prather 2009 Metabolic engineering of Escherichia coli for enhanced production of (R)- and (S)-3-hydroxybutyrate Appl Environ Microbiol 75 3137 3145
62. Uh HS, Lee MJ (2002) Preparation of β-substituted γ-butyrolactone. KP2002-0073751
63. G Wang RI Hollingsworth 1999 Direct conversion of (S)-3-hydroxy-γ- butyrolactone to chiral three carbon building blocks J Org Chem 64 1036 1038
64. G Wang RI Hollingsworth 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
65. G Wang RI Hollingsworth 2000 A simple three-step method for preparing homochiral 5-trityloxymethyl-2-oxazolidinones from optically active 3-hydroxy-γ-butyrolactones Tetrahedron Asymmetry 11 4429 4432
66. M Wolberg MV Filho S Bode P Geilenkirchen R Feldmann A Liese W Hummel M Müller 2008 Chemoenzymatic synthesis of the chiral side-chain of statins: application of an alcohol dehydrogenase catalyzed ketone reduction on a large scale Bioprocess Biosyst Eng 31 183 191
67. G Wu YS Wong X Chen Z Ding 1999 A novel one-step diastereo- and enantioselective formation of trans-azetidinones and its application to the total synthesis of cholesterol absorption inhibitors J Org Chem 64 3714 3718 10.1021/jo990428k 1:CAS:528:DyaK1MXisVGhu70%3D
68. DR Yazbeck CA Martinez S Hu J Tao 2004 Challenges in the development of an efficient enzymatic process in the pharmaceutical industry Tetrahedron Asymmetry 15 2757 2763
69. B Zhou AS Gopalan FV Middlesworth WR Shieh C Shi 1983 Stereochemical control of yeast reductions. 1. Asymmetric synthesis of l-carnitine J Am Chem Soc 105 5925 5926