Enzymatic production of Cilastatin intermediate via highly enantioselective hydrolysis of methyl (±)-2,2-dimethylcyclopropane carboxylate using newly isolated Rhodococcus sp. ECU1013

Applied Microbiology and Biotechnology

Volumn 97, Issue 17, 2013, Pages 7659-7667

  Liu, Chao Hong ^a   Pan, Jiang ^a   Ye, Qin ^a   Xu, Jian He ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Biphasic system; Enantioselective hydrolysis; Methyl 2,2 dimethylcyclopropane carboxylate; Microbial esterase; Rhodococcus sp

Indexed keywords

BIOCHEMISTRY; CARBOXYLATION; ENANTIOSELECTIVITY; ENZYMES; HYDROLYSIS; SUBSTRATES;

BIPHASIC SYSTEMS; ENANTIOSELECTIVE HYDROLYSIS; METHYL 2,2- DIMETHYLCYCLOPROPANE CARBOXYLATE; MICROBIAL ESTERASE; RHODOCOCCUS SP;

ESTERS;

2,2 DIMETHYLCYCLOPROPANE CARBOXYLIC ACID; ALCOHOL; CARBOXYLIC ACID DERIVATIVE; CILASTATIN; ESTERASE; METHYL 2,2 DIMETHYLCYCLOPROPANE CARBOXYLATE; ORGANIC SOLVENT; UNCLASSIFIED DRUG;

BACTERIUM; CARBOXYLIC ACID; ENZYME ACTIVITY; ESTER; HYDROLYSIS; HYDROPHOBICITY; INHIBITOR; OPTICAL PROPERTY;

ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; DISPERSION; ENANTIOSELECTIVITY; HYDROLYSIS; NONHUMAN; RHODOCOCCUS; SCREENING;

RHODOCOCCUS; RHODOCOCCUS SP.;

BACTERIAL PROTEINS; CILASTATIN; CYCLOPROPANES; ESTERASES; HYDROLYSIS; MOLECULAR SEQUENCE DATA; PHYLOGENY; RHODOCOCCUS; SOIL MICROBIOLOGY; STEREOISOMERISM;

EID: 84887068350     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-5038-z     Document Type: Article

References (26)

1. Behrens GA, Hummel A, Padhi SK, Schätzle S, Bornscheuer UT (2011) Discovery and protein engineering of biocatalysts for organic synthesis. Adv Synth Catal 353:2191-2215
2. Bernhardt P, O'Connor SE (2009) Opportunities for enzyme engineering in natural product biosynthesis. Curr Opin Chem Biol 13:1-8
3. Chen CS, Fujimoto YF, Girdaukas G, Sih CJ (1982) Quantitative analyses of biochemical kinetic resolution of enantiomers. J Am Chem Soc 104:7294-7299
4. Clissold SP, Todd PA, Campoli-richands DM (1987) Imipenem/ Cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 33:183-241
5. Graham DW (1987) Measurement and correlation for solubility of (S)-(+)-2,2-dimethyl-cyclopropane carbox amide in different solvents. J Med Chem 30:1074-1089
6. Hupinder PS (2004) Pyrethroid insecticides. Pestic Outlook 4:49-54
7. Jin SJ, Zheng RC, Zheng YG, Shen YC (2008) (R)-enantioselective hydrolysis of 2, 2-dimethylcyclopropanecarboxamide by amidase from a newly isolated strain Brevibacterium epidermidis ZJB-07021. J Appl Microbiol 105:1150-1157
8. Ju X, Yu HL, Pan J, Wei DZ, Xu JH (2010) Bioproduction of chiral mandalate by enantioselective deacylation of α-acetoxyphenylacetic acid using whole cells of newly isolated Pseudomonas sp. ECU1011. Appl Microbiol Biotechnol 86:83-91
9. Kahan FM, Kropp H, Sundelof JG, Birnbaum J (1983) Thienamycin: development of imipenem-Cilastatin. J Antimicrob Chemother 12:S1-S35
10. Kang J, Lim GJ, Yoon SK, KimMY (1995) Asymmetric cyclopropanation using new chiral auxilliaries derived from D-fructose. J Org Chem 60:564-577
11. Katsuda Y (1999) Development of and future prospects for pyrethroid chemistry. Pestic Sci 55:775-782
12. Li AT, Zhang JD, Xu JH, Lu WY, Lin GQ (2009) Isolation of Rhodococcus sp. strain ECU0066, a new sulfide monooxygenaseproducing strain for asymmetric sulfoxidation. Appl Environ Microbiol 75:551-556
13. Liu ZQ, Sun ZH (2004) Cloning and expression of D-lactonohydrolase cDNA from Fusarium moniliforme in Saccharomyces cerevisiae. Biotechnol Lett 26:1861-1865
14. Liu ZQ, Li Y, Ping LF, Xu YY, Cui FF, Xue YP, Zheng YG (2007) Isolation and identification of a novel Rhodococcus sp. ML-0004 producing epoxide hydrolase and optimization of enzyme production. Process Biochem 42:889-894
15. Meul T (1992) Process for resolution of racemates of 2,2- dimethylcyclopropanecarboxylic acid. US patent, US5166417
16. Meul T (1994) Process for the resolution of 2,2- dimethylcyclopropanecarboxylic acid racemates. European patent, EP0461541
17. Mori A, Arai I, Yamamoto H, Nakai H, Arai Y (1986) Asymmetric Simmons-Smith reactions using homochiral protecting groups. Tetrahedron 42:6447-6458
18. Norrby SR, Alestig K, Björnegård B, Burman LÅ, Ferber F, Huber JL, Jones KH, Kahan FM, Kahan JS, Kroop H, Meisinger MAP, Sundelof JG (1983) Urinary recovery of N-forminidoyl thienamycin (MK0787) as affected by coadministration of N-formimidoyl thienamycin dehydropeptidase inhibitors. Antimicrob Agents Chemother 23:300-307
19. Shaw NM, Robins KT, Kiener A (2003) Lonza: 20 years of biotransformations. Adv Synth Catal 345:425-435
20. Thompson JD, Higgins DG, Gibson TJ (1994) CLUSTALW: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position speicific gap penalties and weight matrix choice. Nucleic Acids Res 22:4673-4680
21. Wang MX, Feng GQ (2002) Enzymatic synthesis of optically active 2-methyl-and 2,2-dimethylcyclopropanecarboxylic acids and their derivatives. J Mol Catal B: Enzymatic 18:267-272
22. WangQW,Yang FK, Du H, Hossain MM, Bennett D, Grubisha DS (1998) The synthesis of S-(+)-2,2-dimethylcyclopropane carboxylic acid: a precursor for Cilastatin. Tetrahedron-Asymmetry 9:3971-3977
23. Wang P, Zhu JA, He JY (2010) Enantioselective synthesis of S-(+)-2,2-dimethylcyclopropanecarboxylic acid from ethyl-2,2-dimethylcyclopropa- necarboxylate catalyzed by lipase Novozyme 435. Chin J Catal 31:651-655
24. Yeom SJ, Kim HJ, Oh DK (2007) Enantioselective production of 2,2-dimethylcyclopropane carboxylic acid from 2,2-dimethylcyclopropane carbonitrile using the nitrile hydratase and amidase of Rhodococcus erythropolis ATCC 25544. Enzyme Microb Technol 41:842-848
25. Zheng GW, Yu HL, Zhang JD, Xu JH (2009) Enzymatic production of lmenthol by a high substrate concentration tolerable esterase from newly isolated Bacillus subtilis ECU0054. Adv Synth Catal 351:405-414
26. Zheng RC,Wang YS, Zheng YG (2010) Enantioselective hydrolysis of (R)-2,2-dimethylcyclopropane carboxamide by immobilized cells of an R-amidase-producing bacterium, Delftia tsuruhatensis CCTCC M 205114, on an alginate capsule carrier. J Ind Microbiol Biotechnol 37:503-510