메뉴 건너뛰기




Volumn 25, Issue 3-5, 1999, Pages 455-462

Protease-catalyzed synthesis of disaccharide amino acid esters in organic media

Author keywords

Acylation; Amino acid esters; Optimase M 440; Organic solvents; Subtilisin

Indexed keywords

ACYLATION; AMINO ACIDS; BACTERIA; BIOSYNTHESIS; CATALYSIS; ESTERS; HYDROLYSIS; MOLECULAR STRUCTURE; ORGANIC SOLVENTS; POLYSACCHARIDES; SUGAR (SUCROSE); WATER;

EID: 0033180418     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(99)00040-X     Document Type: Article
Times cited : (33)

References (36)
  • 1
    • 0642367795 scopus 로고
    • Asymmetric transformations catalyzed by enzymes in organic solvents
    • Klibanov A.M. Asymmetric transformations catalyzed by enzymes in organic solvents. Acc Chem Res. 23:1990;114-120.
    • (1990) Acc Chem Res , vol.23 , pp. 114-120
    • Klibanov, A.M.1
  • 2
    • 0027588112 scopus 로고
    • Enzymes in the synthesis of chiral drugs
    • Margolin A.L. Enzymes in the synthesis of chiral drugs. Enzyme Microb Technol. 15:1993;266-280.
    • (1993) Enzyme Microb Technol , vol.15 , pp. 266-280
    • Margolin, A.L.1
  • 3
    • 0030785388 scopus 로고    scopus 로고
    • Application of biocatalysts and biotransformations to the synthesis of pharmaceuticals
    • Zaks A., Dodds D.R. Application of biocatalysts and biotransformations to the synthesis of pharmaceuticals. Drug Dev Today. 2:1997;513-531.
    • (1997) Drug Dev Today , vol.2 , pp. 513-531
    • Zaks, A.1    Dodds, D.R.2
  • 4
    • 0027632206 scopus 로고
    • Enzymatic synthesis of food ingredients in low-water media
    • Vulfson E.N. Enzymatic synthesis of food ingredients in low-water media. Trends Food Sci Technol. 4:1993;209-215.
    • (1993) Trends Food Sci Technol , vol.4 , pp. 209-215
    • Vulfson, E.N.1
  • 5
    • 0031104802 scopus 로고    scopus 로고
    • Why are enzymes less active in organic solvents than in water
    • Klibanov A.M. Why are enzymes less active in organic solvents than in water. Trends Biotechnol. 15:1997;97-101.
    • (1997) Trends Biotechnol , vol.15 , pp. 97-101
    • Klibanov, A.M.1
  • 6
    • 0001901917 scopus 로고
    • Selective removal of protecting groups in carbohydrate chemistry
    • Haines A.H. Selective removal of protecting groups in carbohydrate chemistry. Adv Carbohydr Chem Biochem. 39:1981;13-70.
    • (1981) Adv Carbohydr Chem Biochem , vol.39 , pp. 13-70
    • Haines, A.H.1
  • 7
    • 0026409341 scopus 로고
    • Enzymic methods in preparative carbohydrate chemistry
    • David S., Auge C., Gautheron C. Enzymic methods in preparative carbohydrate chemistry. Adv Carbohydr Chem Biochem. 49:1991;175-237.
    • (1991) Adv Carbohydr Chem Biochem , vol.49 , pp. 175-237
    • David, S.1    Auge, C.2    Gautheron, C.3
  • 8
    • 0000680497 scopus 로고
    • Enzymatic protecting group techniques
    • Waldmann H., Sebastian D. Enzymatic protecting group techniques. Chem Rev. 94:1994;911-937.
    • (1994) Chem Rev , vol.94 , pp. 911-937
    • Waldmann, H.1    Sebastian, D.2
  • 9
    • 0000965821 scopus 로고
    • The chemistry of sucrose
    • Khan R. The chemistry of sucrose. Adv Carbohydr Chem Biochem. 33:1976;235-294.
    • (1976) Adv Carbohydr Chem Biochem , vol.33 , pp. 235-294
    • Khan, R.1
  • 10
    • 0026128949 scopus 로고
    • Enzymatic synthesis of sucrose-containing linear polyester in nearly anhydrous media
    • Patil D.R., Rethwisch D.G., Dordick J.S. Enzymatic synthesis of sucrose-containing linear polyester in nearly anhydrous media. Biotechnol Bioeng. 37:1991;639-646.
    • (1991) Biotechnol Bioeng , vol.37 , pp. 639-646
    • Patil, D.R.1    Rethwisch, D.G.2    Dordick, J.S.3
  • 11
    • 0026674982 scopus 로고
    • Enzymatic and chemoenzymatic approaches to polymer synthesis
    • Dordick J.S. Enzymatic and chemoenzymatic approaches to polymer synthesis. Trends Biotechnol. 10:1992;287-293.
    • (1992) Trends Biotechnol , vol.10 , pp. 287-293
    • Dordick, J.S.1
  • 12
    • 0001683177 scopus 로고
    • Chemoenzymatic synthesis of linear poly(sucrose)acrylate: Optimization of enzymatic activity and polymerization conditions
    • Chen X., Johnson A., Dordick J.S., Rethwich D.G. Chemoenzymatic synthesis of linear poly(sucrose)acrylate optimization of enzymatic activity and polymerization conditions . Macromol Chem Phys. 195:1994;3567-3578.
    • (1994) Macromol Chem Phys , vol.195 , pp. 3567-3578
    • Chen, X.1    Johnson, A.2    Dordick, J.S.3    Rethwich, D.G.4
  • 13
    • 33845279035 scopus 로고
    • Lipase-catalyzed irreversible transesterifications using enol esters as acylation reagents: Preparative enantio- And regioselective synthesis of alcohols, glycerol derivatives, sugars and organometallics
    • Wang Y.F., Lalonde J.J., Momogan M., Bergbreiter D.E., Wong C-H. Lipase-catalyzed irreversible transesterifications using enol esters as acylation reagents preparative enantio- and regioselective synthesis of alcohols, glycerol derivatives, sugars and organometallics . J Am Chem Soc. 110:1988;7200-7205.
    • (1988) J Am Chem Soc , vol.110 , pp. 7200-7205
    • Wang, Y.F.1    Lalonde, J.J.2    Momogan, M.3    Bergbreiter, D.E.4    Wong, C.-H.5
  • 14
    • 0030290099 scopus 로고    scopus 로고
    • Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters
    • Sarney D.B., Baarnard M.J., MacManus D.A., Vulfson E.N. Application of lipases to the regioselective synthesis of sucrose fatty acid monoesters. J Am Oil Chem Soc. 73:1996;1481-1487.
    • (1996) J Am Oil Chem Soc , vol.73 , pp. 1481-1487
    • Sarney, D.B.1    Baarnard, M.J.2    MacManus, D.A.3    Vulfson, E.N.4
  • 15
    • 0030569896 scopus 로고    scopus 로고
    • Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase
    • Oosterom M.W., Rantwijk F., Sheldon R.A. Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase. Biotechnol Bioeng. 49:1996;328-333.
    • (1996) Biotechnol Bioeng , vol.49 , pp. 328-333
    • Oosterom, M.W.1    Rantwijk, F.2    Sheldon, R.A.3
  • 16
    • 0346996064 scopus 로고
    • Facile enzymatic preparation of monoacylated sugars in pyridine
    • Therisod M., Klibanov A.M. Facile enzymatic preparation of monoacylated sugars in pyridine. J Am Chem Soc. 10:1986;5638-5640.
    • (1986) J Am Chem Soc , vol.10 , pp. 5638-5640
    • Therisod, M.1    Klibanov, A.M.2
  • 17
    • 37049090990 scopus 로고
    • Enzymatic synthesis of various 117-O-sucrose and 1-O-fructose esters
    • Carrea G., Riva S., Secundo F. Enzymatic synthesis of various 117-O-sucrose and 1-O-fructose esters. J Chem Soc Perkin Trans I. 5:1989;1057-1061.
    • (1989) J Chem Soc Perkin Trans I , vol.5 , pp. 1057-1061
    • Carrea, G.1    Riva, S.2    Secundo, F.3
  • 18
    • 33845280481 scopus 로고
    • Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide
    • Riva S., Chopineau J., Kieboom A.P.G., Klibanov A.M. Protease-catalyzed regioselective esterification of sugars and related compounds in anhydrous dimethylformamide. J Am Chem Soc. 110:1988;584-589.
    • (1988) J Am Chem Soc , vol.110 , pp. 584-589
    • Riva, S.1    Chopineau, J.2    Kieboom, A.P.G.3    Klibanov, A.M.4
  • 19
    • 2442514886 scopus 로고    scopus 로고
    • Reverse hydrolysis reaction in aqueous medium without any cosolvent. Application of glycosidic esters of tyrosine
    • Cameleyere X., Bouchu A., Guibert A., Combes D. Reverse hydrolysis reaction in aqueous medium without any cosolvent. Application of glycosidic esters of tyrosine. Appl Biochem Biotechnol. 62:1997;61-69.
    • (1997) Appl Biochem Biotechnol , vol.62 , pp. 61-69
    • Cameleyere, X.1    Bouchu, A.2    Guibert, A.3    Combes, D.4
  • 20
  • 21
    • 0001304872 scopus 로고
    • Hydrolytically degradable amino acid containing polymer
    • Staubli A., Ron E., Langer R. Hydrolytically degradable amino acid containing polymer. J Am Chem Soc. 112:1990;4419-4424.
    • (1990) J Am Chem Soc , vol.112 , pp. 4419-4424
    • Staubli, A.1    Ron, E.2    Langer, R.3
  • 23
    • 0028192081 scopus 로고
    • Enzymatic synthesis of various aromatic polyesters in anhydrous organic solvents
    • Park H.G., Chang H.N., Dordick J.S. Enzymatic synthesis of various aromatic polyesters in anhydrous organic solvents. Biocatalysis. 11:1995;263-271.
    • (1995) Biocatalysis , vol.11 , pp. 263-271
    • Park, H.G.1    Chang, H.N.2    Dordick, J.S.3
  • 24
    • 0000557473 scopus 로고
    • Enzymatic synthesis of N- And O-linked glycopeptides
    • Wong C.-H., Schuster M., Wang P., Sears P. Enzymatic synthesis of N- and O-linked glycopeptides. J Am Chem Soc. 115:1993;5893-5901.
    • (1993) J Am Chem Soc , vol.115 , pp. 5893-5901
    • Wong, C.-H.1    Schuster, M.2    Wang, P.3    Sears, P.4
  • 25
    • 0001323502 scopus 로고
    • Incorporation of D-amino acid into peptides via enzymatic condensation in organic solvents
    • Margolin A.L., Tai D.F., Klibanov A.M. Incorporation of D-amino acid into peptides via enzymatic condensation in organic solvents. J Am Chem Soc. 109:1987;7885-7887.
    • (1987) J Am Chem Soc , vol.109 , pp. 7885-7887
    • Margolin, A.L.1    Tai, D.F.2    Klibanov, A.M.3
  • 26
    • 0029968093 scopus 로고    scopus 로고
    • Enzymatic transesterification of monosaccharides and amino acid ester in organic solvents
    • Park O.J., Park H.G., Yang J.W. Enzymatic transesterification of monosaccharides and amino acid ester in organic solvents. Biotechnol Lett. 18:1996;473-478.
    • (1996) Biotechnol Lett , vol.18 , pp. 473-478
    • Park, O.J.1    Park, H.G.2    Yang, J.W.3
  • 27
    • 33947487166 scopus 로고
    • Gas liquid chromatography of trimethylsilyl derivatives of sugars and related substances
    • Sweeley C.C., Bentley R., Makita M., Wells W.W. Gas liquid chromatography of trimethylsilyl derivatives of sugars and related substances. J Am Chem Soc. 85:1963;2497-2507.
    • (1963) J Am Chem Soc , vol.85 , pp. 2497-2507
    • Sweeley, C.C.1    Bentley, R.2    Makita, M.3    Wells, W.W.4
  • 28
    • 0001649196 scopus 로고
    • Esterification of N-protected amino acids with alcohol/carbodiimide/4-(dimethylamino)pyridine: Racemization of glutamic acid and aspartic acid derivatives
    • Dhaon M.K., Olsen R.K., Ramasamy R. Esterification of N-protected amino acids with alcohol/carbodiimide/4-(dimethylamino)pyridine racemization of glutamic acid and aspartic acid derivatives . J Org Chem. 47:1982;1962-1965.
    • (1982) J Org Chem , vol.47 , pp. 1962-1965
    • Dhaon, M.K.1    Olsen, R.K.2    Ramasamy, R.3
  • 29
    • 0001690117 scopus 로고
    • Amberlyst-15, a practical, mild and selective catalyst for methyl esterification of carboxylic acids
    • Petrini M., Ballini R., Marcantoni E., Rosini G. Amberlyst-15, a practical, mild and selective catalyst for methyl esterification of carboxylic acids. Synth Commun. 18:1988;847-853.
    • (1988) Synth Commun , vol.18 , pp. 847-853
    • Petrini, M.1    Ballini, R.2    Marcantoni, E.3    Rosini, G.4
  • 30
    • 84981839954 scopus 로고
    • ̈uber aktivierte ester: Synthese aktivierte ester von aminos̈aure derivaten
    • Schwyzer R., Freuer M., Iselin B., Kägi H. ̈Uber aktivierte ester: synthese aktivierte ester von aminos̈aure derivaten. Helv Chim Acta. 38:1955;80-83.
    • (1955) Helv Chim Acta , vol.38 , pp. 80-83
    • Schwyzer, R.1    Freuer, M.2    Iselin, B.3    Kägi, H.4
  • 31
    • 0348053809 scopus 로고
    • Preservation of membranes in anhydrobiotic organisms
    • Crowe J.H., Crowe L.M., Chapman D. Preservation of membranes in anhydrobiotic organisms. Science. 223:1984;701-703.
    • (1984) Science , vol.223 , pp. 701-703
    • Crowe, J.H.1    Crowe, L.M.2    Chapman, D.3
  • 32
    • 0028838470 scopus 로고
    • Trehalose and sucrose protect both membranes and proteins in intact bacteria during drying
    • Leslie S.B., Israeli E., Lighthart B., Crowe J.H., Crowe L.M. Trehalose and sucrose protect both membranes and proteins in intact bacteria during drying. Appl Environ Microbiol. 61:1995;3592-3597.
    • (1995) Appl Environ Microbiol , vol.61 , pp. 3592-3597
    • Leslie, S.B.1    Israeli, E.2    Lighthart, B.3    Crowe, J.H.4    Crowe, L.M.5
  • 33
    • 85004571395 scopus 로고
    • 13C-Nuclear magnetic resonance (NMR) spectra of O-acylglucoses: Additivity of shift parameters and its application to structure elucidation
    • 13C-Nuclear magnetic resonance (NMR) spectra of O-acylglucoses additivity of shift parameters and its application to structure elucidation . Chem Pharm Bull. 28:1980;2065-2074.
    • (1980) Chem Pharm Bull , vol.28 , pp. 2065-2074
    • Yoshimoto, K.1    Itatani, Y.2    Tsuda, Y.3
  • 34
    • 0029636231 scopus 로고
    • Controlling enzyme-catalyzed regioselectivity in sugar ester synthesis
    • Rich J.O., Bedell B.A., Dordick J.S. Controlling enzyme-catalyzed regioselectivity in sugar ester synthesis. Biotechnol Bioeng. 45:1995;426-434.
    • (1995) Biotechnol Bioeng , vol.45 , pp. 426-434
    • Rich, J.O.1    Bedell, B.A.2    Dordick, J.S.3
  • 35
    • 0028396938 scopus 로고    scopus 로고
    • Thermodynamic predictions for biocatalysis in nonconventional media: Theory, tests, and recommendations for experimental design and analysis
    • Halling P.J. Thermodynamic predictions for biocatalysis in nonconventional media theory, tests, and recommendations for experimental design and analysis . Enzyme Microb Technol. 16:1996;178-206.
    • (1996) Enzyme Microb Technol , vol.16 , pp. 178-206
    • Halling, P.J.1
  • 36
    • 77957000415 scopus 로고
    • The subtilisins
    • G.E. Perlmann, Lorand L. New York: Academic Press
    • Ottesen M., Svensen I. The subtilisins. Perlmann G.E., Lorand L. Methods in enzymology. Proteolytic enzymes. Vol. XIX:1970;199-215 Academic Press, New York.
    • (1970) Methods in Enzymology. Proteolytic Enzymes , vol.19 , pp. 199-215
    • Ottesen, M.1    Svensen, I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.