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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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
Ariens E (1984) A basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. Eur J Clin Pharmacol 26:663–668
Bevinakatti HS, Banerji AA (1991) Practical chemoenzymic synthesis of both enantiomers of propranolol. J Org Chem 56:5372–5375
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
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
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
Chang HT, Sharpless KB (1996) A practical route to enantiopure 1, 2-aminoalcohols. Tetrahedron Lett 37:3219–3222
Chen CS, Wu SH, Girdaukas GS, Sih CJ (1982) Quantitative analyses of biochemical kinetic resolution of enantiomers. J Am Chem Soc 104:7294–7299
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
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
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
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
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
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
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
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
Kaimal TNB, Prasad RBN, Rao TC (1992) A practical chemoenzymic route to (S)-(−)-propranolol. Biotechnol Lett 14:21–26
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
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
Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacterial T4. Nature 227:680–685
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
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
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
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
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
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
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
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
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
Veloo RA, Koomen GJ (1993) Synthesis of enantiomerically pure (S)-(−)-propranolol from sorbitol. Tetrahedron Asymmetry 4:2401–2404
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
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
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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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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DOI: https://doi.org/10.1007/s13213-009-0002-y