Integration of newly isolated biocatalyst and resin-based in situ product removal technique for the asymmetric synthesis of (R)-methyl mandelate

Bioprocess and Biosystems Engineering

Volumn 33, Issue 7, 2010, Pages 797-804

  Guo, Jin Ling ^a   Mu, Xiao Qing ^a   Xu, Yan ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

(R) Methyl mandelate; Adsorbent resin; Asymmetric reduction; Biocatalyst; In situ product removal

Indexed keywords

(R)-METHYL MANDELATE; ADSORBENT RESIN; ASYMMETRIC REDUCTION; ASYMMETRIC SYNTHESIS; ENANTIOMETRIC EXCESS; ENANTIOSELECTIVE REDUCTION; IN-SITU; METHYL BENZOYLFORMATE; OPTICALLY ACTIVE PHARMACEUTICALS; OPTIMIZED CONDITIONS; PHARMACEUTICAL INTERMEDIATES; PRODUCT CONCENTRATION; PRODUCT INHIBITION; REACTION PARAMETERS; RESOLVING AGENTS; S.CEREVISIAE; SACCHAROMYCES CEREVISIAE; SCREENING PROCEDURES; WHOLE CELL; WHOLE CELL BIOCATALYSTS;

ADSORPTION; OPTIMIZATION; RESINS; YEAST;

SYNTHESIS (CHEMICAL);

2 PROPANOL; ALCOHOL; DIMETHYL SULFOXIDE; GLUCOSE; GLYCEROL; GLYCOL; LACTOSE; MACROGOL 400; MALTOSE; MANDELIC ACID DERIVATIVE; MANDELIC ACID METHYL ESTER; MANNITOL; METHANOL; RESIN; SUCROSE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BIOCATALYSIS; BIOCATALYST; CHIRALITY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; FUNGAL STRAIN; FUNGUS GROWTH; NONHUMAN; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; PROCESS OPTIMIZATION; REDUCTION; SACCHAROMYCES CEREVISIAE; TEMPERATURE SENSITIVITY;

ABSORPTION; CATALYSIS; GLYOXYLATES; MANDELIC ACIDS; RESINS, SYNTHETIC; SACCHAROMYCES CEREVISIAE; SYSTEMS INTEGRATION;

SACCHAROMYCES CEREVISIAE;

EID: 77956062851     PISSN: 16157591     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00449-009-0401-2     Document Type: Article

References (33)

1. M Breuer K Ditrich T Habicher B Hauer M Kesseler R Sturmer T Zelinski 2004 Industrial methods for the production of optically active intermediates Angew Chem Int Ed 43 788 824 10.1002/anie.200300599 1:CAS:528: DC%2BD2cXhsFyhurY%3D (Pubitemid 39256206)
2. Coppola GM, Schuster HF (2003) Mandelic acid. In: Walter G (ed) Alpha-hydroxy acids in enantioselective syntheses, 2nd edn. Wiley, New York, pp 137-165
3. Furlenmeier A, Quitt P, Vogler K, Lanz P (1976) 6-Acyl derivatives of aminopenicillanic acid. US Patent 3,957,758
4. Bichel H, Kocsis K, Peter H (1978) Cephalosporins having an alpha-acyloxyacetic acid side chain. US Patent 4,067,979
5. JP Surivet JM Vatele 1999 Total synthesis of antitumor Goniothalamus styryllactones Tetrahedron 55 13011 13028 10.1016/S0040-4020(99)00794-2 1:CAS:528:DyaK1MXmvVyjsrs%3D (Pubitemid 29487730)
6. Mills J, Schmiegel KK, Shaw WN (1983) Phenethanolamines, compositions containing the same, and method for effecting weight control. US Patent 4,391,826
7. K Kinbara K Sakai Y Hashimoto H Nohira K Saigo 1996 Design of resolving reagents: p-substituted mandelic acids as resolving reagents for 1-arylalkylamines Tetrahedron Asymmetry 7 1539 1542 10.1016/0957-4166(96)00175-9 1:CAS:528:DyaK28XjvVKnsLg%3D (Pubitemid 26186224)
8. Kesslin G, Kelly KW (1982) Resolution of racemic mandelic acid. US Patent 4,322,548
9. JW Yang B List 2006 Catalytic asymmetric transfer hydrogenation of alpha-ketoesters with Hantzsch esters Org Lett 8 5653 5655 10.1021/ol0624373 1:CAS:528:DC%2BD28XhtFSlsLvP
10. HE Schoemaker D Mink MG Wubbolts 2003 Dispelling the myths-biocatalysis in industrial synthesis Science 299 1694 1697 10.1126/science.1079237 1:CAS:528:DC%2BD3sXitVSjtLk%3D (Pubitemid 36337188)
11. DJ Pollard JM Woodley 2007 Biocatalysis for pharmaceutical intermediates: the future is now Trends Biotechnol 25 66 73 10.1016/j.tibtech.2006.12.005 1:CAS:528:DC%2BD2sXnslGisg%3D%3D (Pubitemid 46109543)
12. UT Strauss K Faber 1999 Deracemization of (±)-mandelic acid using a lipase-mandelate racemase two-enzyme system Tetrahedron Asymmetry 10 4079 4081 10.1016/S0957-4166(99)00436-X 1:CAS:528:DyaK1MXnvVClu70%3D
13. H Groger 2001 Enzymatic routes to enantiomerically pure aromatic alpha-hydroxy carboxylic acids: A further example for the diversity of biocatalysis Adv Synth Catal 343 547 558 10.1002/1615-4169(200108)343:6/ 7<547::AID-ADSC547>3.0.CO;2-A 1:CAS:528:DC%2BD3MXms12rtb8%3D
14. YC He JH Xu J Pan LM Ouyang Y Xu 2008 Preparation of (R)-(-)-mandelic acid and its derivatives from racemates by enantioselective degradation with a newly isolated bacterial strain Alcaligenes sp. ECU0401 Bioprocess Biosyst Eng 31 445 451 10.1007/s00449-007-0181-5 1:CAS:528:DC%2BD1cXosVCjsrk%3D
15. K Nakamura R Yamanaka T Matsuda T Harada 2003 Recent developments in asymmetric reduction of ketones with biocatalysts Tetrahedron Asymmetry 14 2659 2681 10.1016/S0957-4166(03)00526-3 1:CAS:528:DC%2BD3sXnt1yhu7Y%3D (Pubitemid 38443316)
16. A Schmid JS Dordick B Hauer A Kiener M Wubbolts B Witholt 2001 Industrial biocatalysis today and tomorrow Nature 409 258 268 10.1038/35051736 1:CAS:528:DC%2BD3MXlvFWhug%3D%3D (Pubitemid 32144296)
17. MM Kayser MD Mihovilovic J Kearns A Feicht JD Stewart 1999 Baker's yeast-mediated reductions of alpha-keto esters and an alpha-keto-beta-lactam. Two routes to the paclitaxel side chain J Org Chem 64 6603 6608 10.1021/jo9900681 1:CAS:528:DyaK1MXkvF2ru7k%3D (Pubitemid 29426993)
18. HMS Milagre CDF Milagre PJS Moran MHA Santana JAR Rodrigues 2005 Reduction of ethyl benzoylformate mediated by Saccharomyces cerevisiae entrapped in alginate fibers with double gel layers in a continuously operated reactor Enzyme Microb Technol 37 121 125 10.1016/j.enzmictec.2005.02.011 1:CAS:528:DC%2BD2MXjvVKqsro%3D (Pubitemid 40615650)
19. R Kratzer S Egger B Nidetzky 2008 Integration of enzyme, strain and reaction engineering to overcome limitations of baker's yeast in the asymmetric reduction of alpha-keto esters Biotechnol Bioeng 101 1094 1101 10.1002/bit.21980 1:CAS:528:DC%2BD1cXhsVWktLbJ
20. YZ Chen JG Xu XY Xu Y Xia H Lin SW Xia LX Wang 2007 Enantiocomplementary preparation of (S)- and (R)-mandelic acid derivatives via alpha-hydroxylation of 2-arylacetic acid derivatives and reduction of alpha-ketoester using microbial whole cells Tetrahedron Asymmetry 18 2537 2540 10.1016/j.tetasy.2007.09.029 1:CAS:528:DC%2BD2sXhtlKku7fF (Pubitemid 350116568)
21. CM He DL Chang J Zhang 2008 Asymmetric reduction of substituted alpha- and beta-ketoesters by Bacillus pumilus Phe-C3 Tetrahedron Asymmetry 19 1347 1351 10.1016/j.tetasy.2008.05.003 1:CAS:528:DC%2BD1cXnsFOqsrw%3D
22. T Ema S Ide N Okita T Sakai 2008 Highly efficient chemoenzymatic synthesis of methyl (R)-o-chloromandelate, a key intermediate for clopidogrel, via asymmetric reduction with recombinant Escherichia coli Adv Synth Catal 350 2039 2044 10.1002/adsc.200800292 1:CAS:528:DC%2BD1cXhtF2gurjK
23. R Kratzer M Pukl S Egger B Nidetzky 2008 Whole-cell bioreduction of aromatic alpha-keto esters using Candida tenuis xylose reductase and Candida boidinii formate dehydrogenase co-expressed in Escherichia coli Microb Cell Fact 7 12 10.1186/1475-2859-7-37
24. I Hilker MC Gutierrez R Furstoss J Ward R Wohlgemuth V Alphand 2008 Preparative scale Baeyer-Villiger biooxidation at high concentration using recombinant Escherichia coli and in situ substrate feeding and product removal process Nat Protoc 3 546 554 10.1038/nprot.2007.532 1:CAS:528: DC%2BD1cXivFykur0%3D (Pubitemid 351372239)
25. Xu MW, Mu XQ, Xu Y (2009) Enhancement of substrate concentration in microbial stereoinversion through one-pot oxidation and reduction by aqueous two-phase system. Bioprocess Biosyst Eng. doi: 10.1007/s00449-009-0334-9
26. H Kansal UC Banerjee 2009 Enhancing the biocatalytic potential of carbonyl reductase of Candida viswanathii using aqueous-organic solvent system Bioresour Technol 100 1041 1047 10.1016/j.biortech.2008.08.042 1:CAS:528:DC%2BD1cXhtlOhtL%2FM
27. SG Burton DA Cowan JM Woodley 2002 The search for the ideal biocatalyst Nat Biotechnol 20 37 45 10.1038/nbt0102-37 1:CAS:528:DC%2BD38XislSisw%3D%3D (Pubitemid 34044913)
28. B Pscheidt A Glieder 2008 Yeast cell factories for fine chemical and API production Microb Cell Fact 7 1 49 10.1186/1475-2859-7-25
29. RS Phillips 1996 Temperature modulation of the stereochemistry of enzymatic catalysis: Prospects for exploitation Trends Biotechnol 14 13 16 10.1016/0167-7799(96)80908-5 1:CAS:528:DyaK28Xos1Sjuw%3D%3D (Pubitemid 26037476)
30. T Sakai 2004 'Low-temperature method' for a dramatic improvement in enantioselectivity in lipase-catalyzed reactions Tetrahedron Asymmetry 15 2749 2756 10.1016/j.tetasy.2004.07.058 1:CAS:528:DC%2BD2cXnvFWrs7o%3D (Pubitemid 39278000)
31. R Leon P Fernandes HM Pinheiro JMS Cabral 1998 Whole-cell biocatalysis in organic media Enzyme Microb Technol 23 483 500 10.1016/S0141-0229(98)00078-7 1:CAS:528:DyaK1cXntVCku7Y%3D (Pubitemid 29070751)
32. Y Chen H Lin X Xu S Xia L Wang 2008 Preparation the key intermediate of angiotensin-converting enzyme (ACE) inhibitors: High enantioselective production of ethyl (R)-2-hydroxy-4-phenylbutyrate with Candida boidinii CIOC21 Adv Synth Catal 350 426 430 10.1002/adsc.200700420 1:CAS:528:DC%2BD1cXltFOjsL8%3D
33. K Goldberg K Schroer S Lutz 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 10.1007/s00253-007-1005-x 1:CAS:528:DC%2BD2sXotVOgt7k%3D (Pubitemid 47101672)