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An intracellular esterase from Bacillus cereus catalyzing hydrolysis of 1-chloro-3-(1-napthyloxy)-2-acetoxypropanol

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Abstract

An esterase from Bacillus cereus that hydrolyzes 1-chloro-3-(1-napthyloxy)-2-acetoxypropanol was purified to homogeneity. After purification, the molecular mass of the esterase was determined as 43 kDa by SDS-PAGE, and estimated as 45 kDa using gel filtration, suggesting that the enzyme is a monomer. The optimum pH and temperature for activity of the enzyme were 7.0 and 40°C respectively. The N-terminal sequence was determined. Whole cells of this strain were applied to the resolution of 1-chloro-3-(1-napthyloxy)-2-acetoxypropanol.

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References

  • Ader U, Schneider MP (1992) Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers. I. A facile screening method for suitable biocatalysts. Tetrahedron: Asymmetry 3:201–204

    Article  CAS  Google Scholar 

  • Ariens E (1984) A basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. Eur J Clin Pharmacol 26:663–668

    Article  CAS  PubMed  Google Scholar 

  • Bevinakatti HS, Banerji AA (1991) Practical chemoenzymic synthesis of both enantiomers of propranolol. J Org Chem 56:5372–5375

    Article  CAS  Google Scholar 

  • Bianchi D, Cesti P, Battistel E (1988) Anhydrides as acylating agents in lipase-catalyzed stereoselective esterification of racemic alcohols. J Org Chem 53:5531–5534

    Article  CAS  Google Scholar 

  • Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quanties of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248–254

    Article  CAS  PubMed  Google Scholar 

  • Brookes IK, Lilly MP (1986) Stereospecific hydrolysis of d, l-menthyl acetate by Bacillus subtilis; mass-transfer interactions in a liquid–liquid system. Enzyme Microb Technol 8:53–57

    Article  CAS  Google Scholar 

  • Chang HT, Sharpless KB (1996) A practical route to enantiopure 1, 2-aminoalcohols. Tetrahedron Lett 37:3219–3222

    Article  CAS  Google Scholar 

  • Chen CS, Wu SH, Girdaukas GS, Sih CJ (1982) Quantitative analyses of biochemical kinetic resolution of enantiomers. J Am Chem Soc 104:7294–7299

    Article  CAS  Google Scholar 

  • Chiou TW, Cheng CC, Chung TL, Dar FT (1997) Kinetic resolution of propranolol by a lipase-catalyzed N-acetylation. Bioorg Med Chem Lett 7:433–436

    Article  CAS  Google Scholar 

  • Di Nunno L, Franchini C, Scilimati A, Sinicropi MS, Tortorella P (2000) Chemical and chemoenzymatic routes to 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol, a precursor of drugs with potential β-blocker activity. Tetrahedron Asymmetry 11:1571–1583

    Article  Google Scholar 

  • Fox GE, Pechman KR, Woese CR (1977) Comparative cataloguing of 16S ribosomal ribonucleic acid: molecular approach to procaryotic systematic. Int J Syst Bacteriol 27:44–57

    Article  CAS  Google Scholar 

  • Fuganti C, Grasselli P, Seneci PF, Servi S (1986) Immobilized benzylpenicillin acylase: application to the synthesis of optically active forms of carnitin and propranolol. Tetrahedron Lett 27:2061–2062

    Article  CAS  Google Scholar 

  • Hiroaki S, Takeyuki S, Noriie I, Koichi T, Tadamasa D, Kimio O, Masakatsu S (1993) Catalytic asymmetric nitroaldol reaction using optically active rare earth BINOL complexes, investigation of the catalyst structure. J Am Chem Soc 115:10372–10373

    Article  Google Scholar 

  • Howe R, Shanks RG (1968) β-adrenergic blocking agents. iii the optical isomers of pronethalol, propranolol, and several related compounds. J Med Chem 11:1118–1121

    Article  CAS  PubMed  Google Scholar 

  • Hsu SH, Wu SS, Wang YF (1990) Lipase-catalyzed irreversible transesterification using enol esters: XAD-8 immobilized lipoprotein lipase-catalyzed resolution of secondary alcohols. Tetrahedron Lett 31:6403–6406

    Article  CAS  Google Scholar 

  • Jackson MA, Labeda DA, Becker LA (1995) Enantioselective hydrolysis of ethyl 2-hydroxyalkanoates by an extracelluar esterase from a B. sphaericus strain. Enzyme Microb Technol 17:175–179

    Article  CAS  Google Scholar 

  • Kaimal TNB, Prasad RBN, Rao TC (1992) A practical chemoenzymic route to (S)-(−)-propranolol. Biotechnol Lett 14:21–26

    Article  CAS  Google Scholar 

  • Kapoor M, Anand N, Koul S, Chimni SS, Manhas KS, Raina C, Parshad R, Taneja SC, Qazi GN (2003) Kinetic resolution of 1-chloro-3-(1-naphthyloxy)-2-propanol, an intermediate in the synthesis of β-adrenergic receptor blockers. Bioorg Chem 31:259–269

    Article  CAS  PubMed  Google Scholar 

  • Klunder JM, Ko SY, Sharpless KB (1986) Asymmetric epoxidation of allyl alcohol: efficient routes to homochiral β-adrenergic blocking agents. J Org Chem 51:3710–3712

    Article  CAS  Google Scholar 

  • Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacterial T4. Nature 227:680–685

    Article  CAS  PubMed  Google Scholar 

  • Mitsui R, Shinya S, Ichiyama Y, Kudo K, Tsuno T, Tanaka M (2007) Site-specific and asymmetric hydrolysis of prochiral 2-phenyl-1, 3-propanediol diacetate by a bacterial esterase from an isolated strain. Biosci Biotechnol Biochem 71:1858–1864

    Article  CAS  PubMed  Google Scholar 

  • Molinari F, Brenna O, Valenti M, Aragozzini F (1996) Isolation of a novel carboxylesterase from Bacillus coagulans with high enantioselectivity toward racemic esters of 1, 2-O-isopropylideneglycerol. Enzyme Microb Technol 19:551–556

    Article  CAS  Google Scholar 

  • Noritada M, Nobuo O (1985) Preparation of optically active 1-acetoxy-2-aryloxypropionitriles and its application to a facile synthesis of (S)-(−)-propranolol. Tetrahedron Lett 26:5533–5534

    Article  Google Scholar 

  • Pchelka BK, Loupy A, Plenkiewicz J, Blanco L (2000) Resolution of racemic 1-azido-3-aryloxy-2-propanols by lipase-catalyzed enantioselective acetylation. Tetrahedron Asymmetry 11:2719–2732

    Article  CAS  Google Scholar 

  • Quax WJ, Broekhuizen CP (1994) Development of a new Bacillus carboxyl esterase for use in the resolution of chiral drugs. Appl Microbiol Biotechnol 41:425–431

    CAS  PubMed  Google Scholar 

  • Romano D, Falcioni F, Mora D, Molinari F, Buth A, Ansorge-Schumacher M (2005) Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1, 2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes. Tetrahedron Asymmetry 16:841–845

    Article  CAS  Google Scholar 

  • Sharpless KB, Amberg W, Bennani YL, Crispino GA, Hartung J, Jeong KS, Kwong HL, Morikawa K, Wang ZM, Xu D, Zhang XL (1992) The osmium-catalyzed asymmetric dihydroxylation: a new ligand class and a process improvement. J Org Chem 57:2768–2771

    Article  CAS  Google Scholar 

  • Subhash VD, Prashant NP, Manikrao MS (2000) Biotransformations with Rhizopus arrhizus and Geotrichum candidum for the preparation of (S)-atenolol and (S)-propranolol. Bioorg Med Chem 8:2067–2070

    Article  Google Scholar 

  • Takuya K, Naho A, Satoko N, Tsutomu I, Shizuo N (2001) Synthesis of enantiomeric 4-hydroxypropranolols from 1, 4-dihydroxynaphthalene. Tetrahedron Asymmetry 12:791–795

    Article  Google Scholar 

  • Veloo RA, Koomen GJ (1993) Synthesis of enantiomerically pure (S)-(−)-propranolol from sorbitol. Tetrahedron Asymmetry 4:2401–2404

    Article  CAS  Google Scholar 

  • Wang JJ, Zheng GJ, Wang JL (2001) Studies on chiral separation of β-blockers and their analogues by capillary electrophoresis. Chin J Anal Chem 65:782–787

    Google Scholar 

  • Yoshiyasu T, Masakazu M, Kazuo A, Toshiyuki N, Minoru A, Minoru K (1988) Highly efficient lipase-catalyzed asymmetric synthesis of chiral glycerol derivatives leading to practical synthesis of S-propranolol. Tetrahedron Lett 29:5173–5176

    Article  Google Scholar 

Download references

Acknowledgments

This work was supported by the Youth fund of the State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences and the Open fund of the State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences (No. SKLMR-080604).

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Authors and Affiliations

  1. State Key Laboratory of Microbial Resources, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, People’s Republic of China

    Jianjun Wang & Cong Min

  2. State Key Laboratory of Chemical Resources Engineering, Beijing University of Chemical Technology, Beijing, 100029, People’s Republic of China

    Guojun Zheng

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  1. Jianjun Wang
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  2. Cong Min
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  3. Guojun Zheng
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Correspondence to Guojun Zheng.

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Wang, J., Min, C. & Zheng, G. An intracellular esterase from Bacillus cereus catalyzing hydrolysis of 1-chloro-3-(1-napthyloxy)-2-acetoxypropanol. Ann Microbiol 60, 59–64 (2010). https://doi.org/10.1007/s13213-009-0002-y

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