Efficient asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one by Candida parapsilosis cells in an ionic liquid-containing system

PLoS ONE

Volumn 7, Issue 5, 2012, Pages

  Zhang, Bo Bo ^a,b   Lou, Wen Yong ^a   Chen, Wen Jing ^a   Zong, Min Hua ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b JIANGNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2' HYDROXYL)ETHYL 3 METHYLIMIDAZOLIUM NITRATE; 4 (TRIMETHYLSILYL) 3 BUTYN 2 ONE; BUFFER; IONIC LIQUID; ORGANOSILICON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOCOMPATIBILITY; CANDIDA PARAPSILOSIS; CELL FUNCTION; CONCENTRATION (PARAMETERS); FUNGAL CELL; HYDROPHILICITY; IMMOBILIZED CELL; NONHUMAN; PH; REACTION TIME; REDUCTION; RELIABILITY; TEMPERATURE;

BUTANONES; CANDIDA; CELLS, IMMOBILIZED; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IONIC LIQUIDS; OXIDATION-REDUCTION; SOLVENTS; TEMPERATURE; TRIMETHYLSILYL COMPOUNDS;

CANDIDA PARAPSILOSIS;

EID: 84861472529     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0037641     Document Type: Article

References (41)

1. Zhu XD, Giacobini E, Hornsperger JM, (1995) Effect of MDL 73,745 on acetylcholine and biogenic amine levels in rat cortex. Eur J Pharmacol 276: 93-99.
2. Nicander L, (1975) Changes produced in the male genital organs of rabbits and dogs by 2,6-cis-diphenylhexamethyl-cyclotetrasiloxane (KABI 1774). Acta Pharmacol Toxicol 36: 40-54.
3. Shibata J, Murakami K, Wierzba K, Aoyagi Y, Hashimoto A, et al. (2000) Anticancer effect of 4-[3,5-bis(trimethylsilyl) benzamido] benzoic acid (TAC-101) against A549 nonsmall cell lung cancer cell line is related to its anti-invasive activity. Anticancer Res 20: 3169-3176.
4. Tacke R, Merget M, Bertermann R, Bernd M, Beckers T, Reissmann T, (2000) Syntheses and properties of silicon-and germanium-containing α-amino acids and peptides: A study on C/Si/Ge bioisosterism. Organometallics 19: 3486-3497.
5. Nakamura K, Yamanaka R, Matsuda T, Harada T, (2003) Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron: Asym 14: 2659-2681.
6. Patel RN, (2002) Microbial/enzymatic synthesis of chiral intermediates for pharmaceuticals. Enzyme Microb Technol 31: 804-826.
7. Kolasa T, Gunn DE, Stewart AO, Brooks CDW, (1996) Synthesis and resolution of 2-(cyclohexyl-4-(2-quinolylmethoxy)phenyl)methoxyiminopropionic acid, leukotriene biosynthesis inhibitors. Tetrahedron: Asym 7: 729-736.
8. de Carvalho CCCR, (2011) Enzymatic and whole cell catalysis: Finding new strategies for old processes. Biotechnol Adv 29: 75-83.
9. Schubert T, Hummel W, Kula MR, Muller M, (2001) Enantioselective synthesis of both enantiomers of various propargylic alcohols by use of two oxidoreductases. Eur J Org Chem 22: 4181-4187.
10. Nie Y, Xu Y, Mu XQ, (2004) Highly enantioselective conversion of racemic 1-phenyl-1,2-ethanediol by stereoinversion involving a novel cofactor-dependent oxidoreduction system of Candida parapsilosis CCTCC M203011. Org Process 8: 246-251.
11. Nie Y, Xu Y, Mu XQ, Wang HY, Yang M, et al. (2007) Purification, characterization, gene cloning, and expression of a novel alcohol dehydrogenase with anti-prelog stereospecificity from Candida parapsilosis. Appl Environ Microbiol 73: 3759-3764.
12. Zhang BB, Lou WY, Zong MH, Wu H, (2008) Efficient synthesis of enantiopure (S)-4-(trimethylsilyl)-3-butyn-2-ol via asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one with immobilized Candida parapsilosis CCTCC M203011 cells. J Mol Catal B: Enzym 54: 122-129.
13. Lou WY, Chen L, Zhang BB, Simth TJ, Zong MH, (2009) Using a water-immiscible ionic liquid to improve asymmetric reduction of 4-(trimethylsilyl)-3-butyn-2-one catalyzed by immobilized Candida parapsilosis CCTCC M203011 cells. BMC biotechnol 9: 90-101.
14. Ranke J, Stolte S, Strmann R, Arning J, Jastorff B, (2007) Design of sustainable chemical products the example of ionic liquids. Chem Rev 107: 2183-2206.
15. Stolte S, Matzke M, Arning J, Boschen A, Pitner WR, et al. (2007) Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids. Green Chem 9: 1170-1179.
16. Cornmell RJ, Winder CL, Tiddy GJT, Goodacre R, Stephens G, (2008) Accumulation of ionic liquids in Escherichia coli cells. Green Chem 10: 836-841.
17. Dipeolu O, Green E, Stephens G, (2009) Effects of water-miscible ionic liquids on cell growth and nitro reduction using Clostridium sporogenes. Green Chem 11: 397-401.
18. Kohlmann C, Robertz N, Leuchs S, Dogan Z, Lütz S, et al. (2011) Ionic liquid facilitates biocatalytic conversion of hardly water soluble ketones. J Mol Catal B: Enzym 68: 147-153.
19. Kristensen JB, Borjesson J, Bruun MH, Tjerneld F, Jørgensen H, (2007) Use of surface active additives in enzymatic hydrolysis of wheat straw lignocellulose. Enzyme Microb Technol 40: 888-895.
20. Wood N, Ferguson JL, Gunaratne HQN, Seddon KR, Goodacre R, et al. (2011) Screening ionic liquids for use in biotransformations with whole microbial cells. Green Chem 13: 1843-1851.
21. Zheng L, Zhang S, Yu X, Zhao L, Gao G, et al. (2006) Enhancement of enantioselectivity in lipase-catalyzed resolution of N-(2-ethyl-6-methylphenyl)alanine by additives. J Mol Catal B: Enzym 38: 17-23.
22. de Gonzalo G, Lavandera I, Durchschein K, Wurm D, Faber K, et al. (2007) Asymmetric biocatalytic reduction of ketones using hydroxy-functionalised water-miscible ionic liquids as solvents. Tetrahedron: Asym 18: 2541-2546.
23. Gorke J, Srienc F, Kazlauskas R, (2010) Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnol Bioprocess Eng 15: 40-53.
24. Moniruzzaman M, Nakashima K, Kamiya N, Goto M, (2010) Recent advances of enzymatic reactions in ionic liquids. Biochem Eng J 48: 295-314.
25. Musa MM, Ziegelmann-Fjeld KI, Vieille C, Phillips RS, (2008) Activity and selectivity of W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus in organic solvents and ionic liquids: mono- and biphasic media. Org Biomol Chem 6: 887-892.
26. Lou WY, Wang W, Smith TJ, Zong MH, (2009) Biocatalytic anti-Prelog stereoselective reduction of 4′-methoxyacetophenone to (R)-1-(4-methoxyphenyl)ethanol with immobilized Trigonopsis variabilis AS2.1611 cells using an ionic liquid-containing medium. Green Chem 11: 1377-1384.
27. Lou WY, Wang W, Li RF, Zong MH, (2009) Efficient enantioselective reduction of 4′-methoxyacetophenone with immobilized Rhodotorula sp. AS2.2241 cells in a hydrophilic ionic liquid-containing co-solvent system. J Biotechnol 143: 190-197.
28. Kulacki KJ, Lamberti GA, (2008) Toxicity of imidazolium ionic liquids to freshwater algae. Green Chem 10: 104-110.
29. Li Q, Jiang XL, He YC, Li LZ, Xian M, et al. (2010) Evaluation of the biocompatibile ionic liquid 1-methyl-3-methylimidazolium dimethylphosphite pretreatment of corn cob for improved saccharification. Appl Microbiol Biotechnol 87: 117-126.
30. Baum S, van Rantwijk F, Stolz A, (2012) Application of a eecombinant Escherichia coli whole-cell catalyst expressing hydroxynitrile lyase and nitrilase activities in ionic liquids for the production of (S)-mandelic acid and (S)-mandeloamide. Adv Synth Catal 354: 113-122.
31. Weaver KD, Kim HJ, Sun JZ, MacFarlane DR, Elliott GD, (2010) Cyto-toxicity and biocompatibility of a family of choline phosphate ionic liquids designed for pharmaceutical applications. Green Chem 12: 507-513.
32. Ni Y, Xu JH, (2012) Biocatalytic ketone reduction: A green and efficient access to enantiopure alcohols. Biotechnol Adv, in press doi:10.1016/j.biotechadv.2011.10.007.
33. Bräutigam S, Dennewald D, Schürmann M, Lutje-Spelberg J, Pitner WR, (2009) Whole-cell biocatalysis: Evaluation of new hydrophobic ionic liquids for efficient asymmetric reduction of prochiral ketones. Enzyme Microbl Technol 45: 310-316.
34. Zhao H, (2010) Methods for stabilizing and activating enzymes in ionic liquids - a review. J Chem Technol Biotechnol 85: 891-907.
35. Xie Y, Xu JH, Xu Y, (2010) Isolation of a Bacillus strain producing ketone reductase with high substrate tolerance. Bioresour Technol 101: 1054-1059.
36. Luo F, Lu DF, Gong YF, (2011) Enantioselective bioreduction of 2-fluoro-2-alken-1-ols mediated by Saccharomyces cerevisiae. J Mol Catal B: Enzym 70: 101-107.
37. Matsuda T, Yamanaka R, Nakamura K, (2009) Recent progress in biocatalysis for asymmetric oxidation and reduction. Tetrahedron: Asym 20: 513-557.
38. Kratzer R, Pukl M, Egger S, Vogl M, Brecker L, et al. (2011) Enzyme identification and development of a whole-cell biotransformation for asymmetric reduction of o-chloroacetophenone. Biotechnol Bioeng 108: 797-803.
39. Schroer K, Zelic B, Oldiges M, Lütz S, (2009) Metabolomics for biotransformations: Intracellular redox cofactor analysis and enzyme kinetics offer insight into whole cell processes. Biotechnol Bioeng 104: 251-260.
40. Liu ZQ, Li FF, Cheng F, Zhang T, You ZY, et al. (2011) A novel synthesis of iminodiacetic acid: Biocatalysis by whole Alcaligenes faecalis ZJB-09133 cells from iminodiacetonitrile. Biotechnol Prog 27: 698-705.
41. Itoh T, Han S, Matsushita Y, Hayase S, (2004) Enhanced enantioselectivity and remarkable acceleration on the lipase-catalyzed transesterification using novel ionic liquids. Green Chem 6: 437-439.