메뉴 건너뛰기




Volumn 1, Issue 1, 2014, Pages

Efficient production of l-menthol in a two-phase system with SDS using an immobilized bacillus subtilis esterase

Author keywords

Dl menthyl acetate; Enantioselective hydrolysis; Immobilized bacillus subtilis esterase; L menthol; Organic aqueous biphasic system

Indexed keywords

CLONING; CROSSLINKING; ENANTIOSELECTIVITY; ENZYMATIC HYDROLYSIS; ENZYME ACTIVITY; ENZYME INHIBITION; ESTERS; SULFUR COMPOUNDS;

EID: 85019301565     PISSN: None     EISSN: 21974365     Source Type: Journal    
DOI: 10.1186/s40643-014-0012-x     Document Type: Article
Times cited : (13)

References (32)
  • 2
    • 50349091008 scopus 로고    scopus 로고
    • Aroma chemical profile: Menthol
    • Clark GS (2007) Aroma chemical profile: menthol. Perfum Flavor 32:38–47
    • (2007) Perfum Flavor , vol.32 , pp. 38-47
    • Clark, G.S.1
  • 3
    • 33746752175 scopus 로고    scopus 로고
    • Preparation of a privileged silicon-stereogenic silane: Classical versus kinetic resolution
    • Rendler S, Auer G, Keller M, Oestreich M (2006) Preparation of a privileged silicon-stereogenic silane: classical versus kinetic resolution. Adv Synth Catal 348:1171–1182
    • (2006) Adv Synth Catal , vol.348 , pp. 1171-1182
    • Rendler, S.1    Auer, G.2    Keller, M.3    Oestreich, M.4
  • 4
    • 33646848772 scopus 로고    scopus 로고
    • Synthesis of enantiomeric menthol derivatives for forming and probing chiral surfaces. X-ray crystal and molecular structures of (+)-(1S,2R,5S)-1-(2-tricyanovinyl-1H-pyrrol-1-yl-methoxy)-2-isopropyl-5-methylcycl-ohexane
    • Cattaruzza F, Fares V, Flamini A, Prosperi T (2006) Synthesis of enantiomeric menthol derivatives for forming and probing chiral surfaces. X-ray crystal and molecular structures of (+)-(1S,2R,5S)-1-(2-tricyanovinyl-1H-pyrrol-1-yl-methoxy)-2-isopropyl-5-methylcycl-ohexane. Tetrahedron-Asymmetry 17:1296–1300
    • (2006) Tetrahedron-Asymmetry , vol.17 , pp. 1296-1300
    • Cattaruzza, F.1    Fares, V.2    Flamini, A.3    Prosperi, T.4
  • 5
    • 77956283223 scopus 로고    scopus 로고
    • Hot market for a cool chemical
    • Michael M (2010) Hot market for a cool chemical. Chem Eng News 88:15–16
    • (2010) Chem Eng News , vol.88 , pp. 15-16
    • Michael, M.1
  • 6
    • 84979854953 scopus 로고
    • Separating optically pure d-l-isomers of menthol, neomenthol and isomenthol
    • Fleischer J, Bauer K, Hopp R (1976) Separating optically pure d-l-isomers of menthol, neomenthol and isomenthol. US Patent 3,943,181,
    • (1976) US Patent 3 , vol.943 , pp. 181
    • Fleischer, J.1    Bauer, K.2    Hopp, R.3
  • 7
    • 84888205609 scopus 로고    scopus 로고
    • Natural & synthetic menthol
    • Lawrence BM (ed), CRC, Boca Raton
    • Hopp R, Lawrence BM (2006) Natural & synthetic menthol. In: Lawrence BM (ed) Mint: the genus Mentha. CRC, Boca Raton, p 389
    • (2006) Mint: The Genus Mentha , pp. 389
    • Hopp, R.1    Lawrence, B.M.2
  • 8
    • 0022285493 scopus 로고
    • Asymmetric isomerization of allylic compounds and the mechanism
    • Tani K (1985) Asymmetric isomerization of allylic compounds and the mechanism. Pure Appl Chem 57:1845–1854
    • (1985) Pure Appl Chem , vol.57 , pp. 1845-1854
    • Tani, K.1
  • 9
    • 0001067181 scopus 로고    scopus 로고
    • Enantioselective isomerization of allylamine to enamine: Practical asymmetric synthesis of (−)-menthol by Rh–BINAP catalysts
    • Akutagawa S (1997) Enantioselective isomerization of allylamine to enamine: practical asymmetric synthesis of (−)-menthol by Rh–BINAP catalysts. Top Catal 4:271–274
    • (1997) Top Catal , vol.4 , pp. 271-274
    • Akutagawa, S.1
  • 10
    • 0001594503 scopus 로고
    • Asymmetric synthesis by metal BINAP catalysts
    • Akutagawa S (1995) Asymmetric synthesis by metal BINAP catalysts. Appl Catal A-Gen 128:171–207
    • (1995) Appl Catal A-Gen , vol.128 , pp. 171-207
    • Akutagawa, S.1
  • 12
    • 85052607756 scopus 로고    scopus 로고
    • Process for preparing (−)-menthol and similar compounds
    • Chaplin JA, Gardiner NS, Mitra RK (2006) Process for preparing (−)-menthol and similar compounds. US Patent 7,026,144
    • (2006) US Patent 7 , vol.26 , pp. 144
    • Chaplin, J.A.1    Gardiner, N.S.2    Mitra, R.K.3
  • 14
    • 0029125374 scopus 로고
    • Efficient kinetic resolution of dl-menthol by lipase-catalyzed enantioselective esterification with acid anhydride in fed-batch reactor
    • Xu JH, Kawamoto T, Tanaka A (1995) Efficient kinetic resolution of dl-menthol by lipase-catalyzed enantioselective esterification with acid anhydride in fed-batch reactor. Appl Microbiol Biotechnol 43:402–407
    • (1995) Appl Microbiol Biotechnol , vol.43 , pp. 402-407
    • Xu, J.H.1    Kawamoto, T.2    Tanaka, A.3
  • 15
    • 84881317854 scopus 로고    scopus 로고
    • Enantioselective hydrolysis of dl-menthyl benzoate by cell-free extract of newly isolated Acinetobacter sp. ECU2040
    • Ngo-Thi MT, Yin JG, Pan J, Zheng GW, Xu JH (2013) Enantioselective hydrolysis of dl-menthyl benzoate by cell-free extract of newly isolated Acinetobacter sp. ECU2040. Appl Biochem Biotechnol 170:1974–1981
    • (2013) Appl Biochem Biotechnol , vol.170 , pp. 1974-1981
    • Ngo-Thi, M.T.1    Yin, J.G.2    Pan, J.3    Zheng, G.W.4    Xu, J.H.5
  • 16
    • 0037116425 scopus 로고    scopus 로고
    • Factors affecting the resolution of dl-menthol by immobilized lipase-catalyzed esterification in organic solvent
    • Wang DL, Nag A, Lee GC, Shaw JF (2002) Factors affecting the resolution of dl-menthol by immobilized lipase-catalyzed esterification in organic solvent. J Agric Food Chem 50:262–265
    • (2002) J Agric Food Chem , vol.50 , pp. 262-265
    • Wang, D.L.1    Nag, A.2    Lee, G.C.3    Shaw, J.F.4
  • 17
    • 0142142207 scopus 로고    scopus 로고
    • Enantioselective hydrolysis of D, L-menthyl benzoate to L-(−)-menthol by recombinant Candida rugosa lipase L1P1
    • Vorlova S, Bornscheuer UT, Gatfield I, Hilmer JM, Bertram HJ, Schmid RD (2002) Enantioselective hydrolysis of D, L-menthyl benzoate to L-(−)-menthol by recombinant Candida rugosa lipase L1P1. Adv Synth Catal 344:l152–1155
    • (2002) Adv Synth Catal , vol.344 , pp. 1152-1155
    • Vorlova, S.1    Bornscheuer, U.T.2    Gatfield, I.3    Hilmer, J.M.4    Bertram, H.J.5    Schmid, R.D.6
  • 18
    • 34447270575 scopus 로고    scopus 로고
    • Highly enantioselective hydrolysis of DL-menthyl acetate to L-menthol by whole-cell lipase from Burkholderia cepacia ATCC25416
    • Yu LJ, Xu Y, Wang XQ, Yu XW (2007) Highly enantioselective hydrolysis of DL-menthyl acetate to L-menthol by whole-cell lipase from Burkholderia cepacia ATCC25416. J Mol Catal B-Enzym 47:149–154
    • (2007) J Mol Catal B-Enzym , vol.47 , pp. 149-154
    • Yu, L.J.1    Xu, Y.2    Wang, X.Q.3    Yu, X.W.4
  • 19
    • 85011350328 scopus 로고    scopus 로고
    • Production of L-menthol by immobilized enzyme-catalyzed diastereoselective transesterification
    • Meng Y, Wu JP, Xu G, Yang LR (2010) Production of L-menthol by immobilized enzyme-catalyzed diastereoselective transesterification. Chin J Bioprocess Eng 8:39–44
    • (2010) Chin J Bioprocess Eng , vol.8 , pp. 39-44
    • Meng, Y.1    Wu, J.P.2    Xu, G.3    Yang, L.R.4
  • 20
    • 79960629637 scopus 로고    scopus 로고
    • Resolution of (±)-menthol in ionic liquid catalyzed by immobilized lipase on magnetic microspheres
    • Ren MY, Bai S, Sun Y (2009) Resolution of (±)-menthol in ionic liquid catalyzed by immobilized lipase on magnetic microspheres. Chin J Bioprocess Eng 7:16–20
    • (2009) Chin J Bioprocess Eng , vol.7 , pp. 16-20
    • Ren, M.Y.1    Bai, S.2    Sun, Y.3
  • 21
    • 77950202386 scopus 로고    scopus 로고
    • Comparison of acid anhydrides with carboxylic acids in enantioselective enzymatic esterification of racemic menthol
    • Xu JH, Zhu J, Takuo K, Atsuo T, Hu Y (1997) Comparison of acid anhydrides with carboxylic acids in enantioselective enzymatic esterification of racemic menthol. Chin J Biotechnol 13:387–393
    • (1997) Chin J Biotechnol , vol.13 , pp. 387-393
    • Xu, J.H.1    Zhu, J.2    Takuo, K.3    Atsuo, T.4    Hu, Y.5
  • 22
    • 85052594454 scopus 로고    scopus 로고
    • Screening of stereoselective lipase and its application in resolution of menthol
    • Xu G, Li M, Sun MM, Wu JP, Yang LR (2013) Screening of stereoselective lipase and its application in resolution of menthol. Chin J Bioprocess Eng 11:1–4
    • (2013) Chin J Bioprocess Eng , vol.11 , pp. 1-4
    • Xu, G.1    Li, M.2    Sun, M.M.3    Wu, J.P.4    Yang, L.R.5
  • 23
    • 60849119553 scopus 로고    scopus 로고
    • Enzymatic production of l-menthol by a high substrate concentration tolerable esterase from newly isolated Bacillus subtilis ECU0554
    • Zheng GW, Yu HL, Zhang JD, Xu JH (2009) Enzymatic production of l-menthol by a high substrate concentration tolerable esterase from newly isolated Bacillus subtilis ECU0554. Adv Synth Catal 351:405–414
    • (2009) Adv Synth Catal , vol.351 , pp. 405-414
    • Zheng, G.W.1    Yu, H.L.2    Zhang, J.D.3    Xu, J.H.4
  • 24
    • 77957357538 scopus 로고    scopus 로고
    • An efficient bioprocess for enzymatic production of l-menthol with high ratio of substrate to catalyst using whole cells of recombinant E. Coli
    • Zheng GW, Pan J, Yu HL, Ngo-Thi MT, Li CX, Xu JH (2010) An efficient bioprocess for enzymatic production of l-menthol with high ratio of substrate to catalyst using whole cells of recombinant E. coli. J Biotechnol 150:108–114
    • (2010) J Biotechnol , vol.150 , pp. 108-114
    • Zheng, G.W.1    Pan, J.2    Yu, H.L.3    Ngo-Thi, M.T.4    Li, C.X.5    Xu, J.H.6
  • 25
    • 79954575679 scopus 로고    scopus 로고
    • Immobilization of Bacillus subtilis esterase by simple cross-linking for enzymatic resolution of dl-menthyl acetate
    • Zheng GW, Yu HL, Li CX, Pan J, Xu JH (2011) Immobilization of Bacillus subtilis esterase by simple cross-linking for enzymatic resolution of dl-menthyl acetate. J Mol Catal B-Enzym 70:138–143
    • (2011) J Mol Catal B-Enzym , vol.70 , pp. 138-143
    • Zheng, G.W.1    Yu, H.L.2    Li, C.X.3    Pan, J.4    Xu, J.H.5
  • 26
    • 79952042445 scopus 로고    scopus 로고
    • Significant enhancement of (R)-mandelic acid production by relieving substrate inhibition of recombinant nitrilase in toluene-water biphasic system
    • Zhang ZJ, Pan J, Liu JF, Xu JH, He YC, Liu YY (2011) Significant enhancement of (R)-mandelic acid production by relieving substrate inhibition of recombinant nitrilase in toluene-water biphasic system. J Biotechnol 152:24–29
    • (2011) J Biotechnol , vol.152 , pp. 24-29
    • Zhang, Z.J.1    Pan, J.2    Liu, J.F.3    Xu, J.H.4    He, Y.C.5    Liu, Y.Y.6
  • 27
    • 39149094961 scopus 로고    scopus 로고
    • Improvement of biodesulfurization activity of alginate immobilized cells in biphasic systems
    • Li YG, Xing JM, Xiong XC, Li WL, Gao HS, Liu HZ (2008) Improvement of biodesulfurization activity of alginate immobilized cells in biphasic systems. J Ind Microbiol Biotechnol 35:145–150
    • (2008) J Ind Microbiol Biotechnol , vol.35 , pp. 145-150
    • Li, Y.G.1    Xing, J.M.2    Xiong, X.C.3    Li, W.L.4    Gao, H.S.5    Liu, H.Z.6
  • 28
    • 0034597428 scopus 로고    scopus 로고
    • Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester
    • Liu YY, Xu JH, Hu Y (2000) Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of ketoprofen ester. J Mol Catal B-Enzym 10:523–529
    • (2000) J Mol Catal B-Enzym , vol.10 , pp. 523-529
    • Liu, Y.Y.1    Xu, J.H.2    Hu, Y.3
  • 29
    • 20644469267 scopus 로고
    • Quantitative analyses of biochemical kinetic resolutions of enantiomers
    • Chen CS, Fujimoto Y, Girdaukas G, Sih CJ (1982) Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104:7294–7299
    • (1982) J am Chem Soc , vol.104 , pp. 7294-7299
    • Chen, C.S.1    Fujimoto, Y.2    Girdaukas, G.3    Sih, C.J.4
  • 30
    • 79957851192 scopus 로고    scopus 로고
    • Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor
    • Wang LJ, Li CX, Ni Y, Zhang J, Liu X, Xu JH (2011) Highly efficient synthesis of chiral alcohols with a novel NADH-dependent reductase from Streptomyces coelicolor. Bioresour Technol 102:7023–7028
    • (2011) Bioresour Technol , vol.102 , pp. 7023-7028
    • Wang, L.J.1    Li, C.X.2    Ni, Y.3    Zhang, J.4    Liu, X.5    Xu, J.H.6
  • 31
    • 79960366127 scopus 로고    scopus 로고
    • Highly stereoselective reduction of prochiral ketones by a bacterial reductase coupled with cofactor regeneration
    • Ni Y, Li CX, Wang LJ, Zhang J, Xu JH (2011) Highly stereoselective reduction of prochiral ketones by a bacterial reductase coupled with cofactor regeneration. Org Biomol Chem 9:5463–5468
    • (2011) Org Biomol Chem , vol.9 , pp. 5463-5468
    • Ni, Y.1    Li, C.X.2    Wang, L.J.3    Zhang, J.4    Xu, J.H.5
  • 32
    • 27944447355 scopus 로고    scopus 로고
    • A method to greatly improve the enantioselectivity of lipase-catalyzed hydrolysis using sodium dodecyl sulfate (SDS) as an additive
    • Mori S, Yumoto H, Matsumi R, Nishigaki T, Ebara Y, Ueji S (2005) A method to greatly improve the enantioselectivity of lipase-catalyzed hydrolysis using sodium dodecyl sulfate (SDS) as an additive. Tetrahedron: Asymmetry 16:3698–3702
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 3698-3702
    • Mori, S.1    Yumoto, H.2    Matsumi, R.3    Nishigaki, T.4    Ebara, Y.5    Ueji, S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.