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Volumn 68, Issue 1, 2000, Pages 84-91

Lipase and esterase-catalyzed acylation of hetero-substituted nitrogen nucleophiles in water and organic solvents

Author keywords

Hydrazine; Hydroxylamine; Lipase; Non natural reaction

Indexed keywords

ESTERASE; HETEROCYCLIC NITRO COMPOUND; HYDRAZINE DERIVATIVE; HYDROXYLAMINE; IBUPROFEN; NITROGEN DERIVATIVE; OCTANOIC ACID; ORGANIC SOLVENT; TRIACYLGLYCEROL LIPASE; WATER;

EID: 0034607271     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(20000405)68:1<84::AID-BIT10>3.0.CO;2-5     Document Type: Article
Times cited : (18)

References (52)
  • 1
    • 0025904979 scopus 로고
    • Synthesis of hydrazides through an enzymatic hydrazinolysis reaction
    • Astorga C, Robolledo F, Color V. 1991. Synthesis of hydrazides through an enzymatic hydrazinolysis reaction. Synthesis 350-352.
    • (1991) Synthesis , pp. 350-352
    • Astorga, C.1    Robolledo, F.2    Color, V.3
  • 2
    • 0027474393 scopus 로고
    • Enzymatic hydrazinolysis of diesters of N-aminosuccinimide derivatives
    • Astorga C, Robolledo F, Gotor V. 1993. Enzymatic hydrazinolysis of diesters of N-aminosuccinimide derivatives. Synthesis 287-289.
    • (1993) Synthesis , pp. 287-289
    • Astorga, C.1    Robolledo, F.2    Gotor, V.3
  • 3
    • 0038462471 scopus 로고
    • The chemistry of the azido group
    • Patai S, editor. New York: Interscience
    • Banthorpe DV. 1971. The chemistry of the azido group. In: Patai S, editor. The chemistry of the functional groups. New York: Interscience. p 397-405.
    • (1971) The Chemistry of the Functional Groups , pp. 397-405
    • Banthorpe, D.V.1
  • 4
    • 84990442535 scopus 로고
    • 2+-induced enhancement of the molecular stability of Pseudomonas lipases
    • Van den Tweel JJJ, Harder A, Buitelaar RM, editors. Amsterdam: Elsevier Science Publishers
    • 2+-induced enhancement of the molecular stability of Pseudomonas lipases. In: Van den Tweel JJJ, Harder A, Buitelaar RM, editors. Stability and stabilization of enzymes. Amsterdam: Elsevier Science Publishers. p 181-188.
    • (1993) Stability and Stabilization of Enzymes , pp. 181-188
    • Barfoed, M.1    Borch, K.2    Lund, H.3    Patkar, S.A.4
  • 5
    • 84982367300 scopus 로고
    • The chemistry of hydroxamic acids and N-hydroxyimides
    • Bauer L, Exner O. 1974. The chemistry of hydroxamic acids and N-hydroxyimides. Angew Chem, Int Ed Engl 13:376-384.
    • (1974) Angew Chem, Int Ed Engl , vol.13 , pp. 376-384
    • Bauer, L.1    Exner, O.2
  • 6
    • 37049072114 scopus 로고
    • Lipase mediated formation of peroxycarboxylic acids used in catalytic epoxidation of alkenes
    • Björkling F, Godtfredsen SE, Kirk O. 1990. Lipase mediated formation of peroxycarboxylic acids used in catalytic epoxidation of alkenes. J Chem Soc, Chem Commun 1301-1303.
    • (1990) J Chem Soc, Chem Commun , pp. 1301-1303
    • Björkling, F.1    Godtfredsen, S.E.2    Kirk, O.3
  • 7
    • 0026683073 scopus 로고
    • Lipase catalyzed synthesis of peroxycarboxylic acids and lipase mediated oxidations
    • Björkling F, Frykman H, Godtfredsen SE, Kirk O. 1992. Lipase catalyzed synthesis of peroxycarboxylic acids and lipase mediated oxidations. Tetrahedron 48:4587-4592.
    • (1992) Tetrahedron , vol.48 , pp. 4587-4592
    • Björkling, F.1    Frykman, H.2    Godtfredsen, S.E.3    Kirk, O.4
  • 8
    • 4243817636 scopus 로고
    • Ueber enige eigenschaften und die constitution des freien hydroxylamins und seiner homologen
    • Brühl JW. 1893. Ueber enige Eigenschaften und die Constitution des freien Hydroxylamins und seiner Homologen. Ber Dtsch Chem Ges 26: 2508-2520.
    • (1893) Ber Dtsch Chem Ges , vol.26 , pp. 2508-2520
    • Brühl, J.W.1
  • 9
    • 0026848926 scopus 로고
    • Kinetics of geranyl acetate synthesis by lipase-catalysed transesterification in n-hexane
    • Chulalaksananukul W, Condoret J-S, Combes D. 1992. Kinetics of geranyl acetate synthesis by lipase-catalysed transesterification in n-hexane. Enzyme Microb Technol 14:293-298.
    • (1992) Enzyme Microb Technol , vol.14 , pp. 293-298
    • Chulalaksananukul, W.1    Condoret, J.-S.2    Combes, D.3
  • 10
    • 0015369992 scopus 로고
    • Biochemical and immunochemical comparison of aliphatic amidases produced by Pseudomonas species
    • Clarke PH. 1972. Biochemical and immunochemical comparison of aliphatic amidases produced by Pseudomonas species. J Gen Microbiol 71:241-257.
    • (1972) J Gen Microbiol , vol.71 , pp. 241-257
    • Clarke, P.H.1
  • 15
    • 0028753137 scopus 로고
    • Lipase catalyzed transformations with unnatural acyl acceptors
    • De Zoete MC, Van Rantwijk F, Sheldon RA. 1994b. Lipase catalyzed transformations with unnatural acyl acceptors. Catal Today 22: 563-590.
    • (1994) Catal Today , vol.22 , pp. 563-590
    • De Zoete, M.C.1    Van Rantwijk, F.2    Sheldon, R.A.3
  • 18
    • 0030568591 scopus 로고    scopus 로고
    • Lipase catalyzed ammoniolysis of lipids. A facile synthesis of fatty acid amides
    • Erratum 2: 141-145
    • De Zoete MC, Kock-van Dalen AC, Van Rantwijk F, Sheldon RA. 1996. Lipase catalyzed ammoniolysis of lipids. A facile synthesis of fatty acid amides. J Mol Catal B: Enzymes 1:109-113 [Erratum 2: 141-145].
    • (1996) J Mol Catal B: Enzymes , vol.1 , pp. 109-113
    • De Zoete, M.C.1    Kock-Van Dalen, A.C.2    Van Rantwijk, F.3    Sheldon, R.A.4
  • 19
    • 0032472292 scopus 로고    scopus 로고
    • Study of the acyl transfer activity of a recombinant amidase overproduced in an Escherichia coli strain. Application for short-chain hydroxamic acid and acid hydrazide synthesis
    • Fournand D, Arnaud A, Galzy P. 1998a. Study of the acyl transfer activity of a recombinant amidase overproduced in an Escherichia coli strain. Application for short-chain hydroxamic acid and acid hydrazide synthesis. J Mol Catal B: Enzymes 4:77-90.
    • (1998) J Mol Catal B: Enzymes , vol.4 , pp. 77-90
    • Fournand, D.1    Arnaud, A.2    Galzy, P.3
  • 21
    • 0027451962 scopus 로고
    • Chemoenzymatic aminolysis and ammonolysis of β-keto esters
    • García MJ, Rebolledo F, Gotor V. 1993. Chemoenzymatic aminolysis and ammonolysis of β-keto esters. Tetrahedron Lett 34:6141-6142.
    • (1993) Tetrahedron Lett , vol.34 , pp. 6141-6142
    • García, M.J.1    Rebolledo, F.2    Gotor, V.3
  • 23
    • 84988108146 scopus 로고
    • An improved method for the preparation of acylhydrazines: The first example of an enzymatic hydrazinolysis reaction
    • Gotor V, Astorga C, Rebolledo F. 1990. An improved method for the preparation of acylhydrazines: the first example of an enzymatic hydrazinolysis reaction. Synlett 387-388.
    • (1990) Synlett , pp. 387-388
    • Gotor, V.1    Astorga, C.2    Rebolledo, F.3
  • 24
    • 0001007247 scopus 로고
    • The α-effect in the chemistry of organic compounds
    • Grekov AP, Veselov VY. 1978. The α-effect in the chemistry of organic compounds. Russ Chem Rev 47:631-648.
    • (1978) Russ Chem Rev , vol.47 , pp. 631-648
    • Grekov, A.P.1    Veselov, V.Y.2
  • 25
    • 0030764375 scopus 로고    scopus 로고
    • Formation of achiral hydroxamic acid with an amidase from Rhodococcus erythropolis MP50 and subsequent chemical lossen rearrangement to a chiral amine
    • Hirrlinger B, Stolz A. 1997. Formation of achiral hydroxamic acid with an amidase from Rhodococcus erythropolis MP50 and subsequent chemical Lossen rearrangement to a chiral amine. Appl Environ Microbiol 63:3390-3393.
    • (1997) Appl Environ Microbiol , vol.63 , pp. 3390-3393
    • Hirrlinger, B.1    Stolz, A.2
  • 26
    • 85022245822 scopus 로고
    • Ueber hydroxamsauren der fettreihe
    • Hoffmann C. 1889. Ueber Hydroxamsauren der Fettreihe. Ber Dtsch Chem Ges 22:2854-2856.
    • (1889) Ber Dtsch Chem Ges , vol.22 , pp. 2854-2856
    • Hoffmann, C.1
  • 27
    • 78651147451 scopus 로고
    • Reactions catalyzed by amidases
    • Jacobi WB, Fredericks J. 1964. Reactions catalyzed by amidases. J Biol Chem 239:1978-1982.
    • (1964) J Biol Chem , vol.239 , pp. 1978-1982
    • Jacobi, W.B.1    Fredericks, J.2
  • 28
  • 29
    • 0001501406 scopus 로고
    • Hydroxamic and aminohydroxamic acids and their complexes with metal ions
    • Kurzak B, Kolzlowski H, Farkas E. 1992. Hydroxamic and aminohydroxamic acids and their complexes with metal ions. Coord Chem Rev 114:169-200.
    • (1992) Coord Chem Rev , vol.114 , pp. 169-200
    • Kurzak, B.1    Kolzlowski, H.2    Farkas, E.3
  • 30
    • 0033532852 scopus 로고    scopus 로고
    • Synthesis of primary amides by lipase-catalyzed amidification of carboxylic acids in an organic solvent
    • Cambridge
    • Litjens MJJ, Straathof AJJ, Jongejan JA, Heijnen JJ. 1999. Synthesis of primary amides by lipase-catalyzed amidification of carboxylic acids in an organic solvent. Chem Commun (Cambridge) 1255-1256.
    • (1999) Chem Commun , pp. 1255-1256
    • Litjens, M.J.J.1    Straathof, A.J.J.2    Jongejan, J.A.3    Heijnen, J.J.4
  • 31
    • 0030897974 scopus 로고    scopus 로고
    • Enzymatic synthesis of glycamide surfactants by amidification reaction
    • Maugard T, Remeaud-Simeon M, Petre D, Monsan P. 1997a. Enzymatic synthesis of glycamide surfactants by amidification reaction. Tetrahedron 53:5185-5194.
    • (1997) Tetrahedron , vol.53 , pp. 5185-5194
    • Maugard, T.1    Remeaud-Simeon, M.2    Petre, D.3    Monsan, P.4
  • 32
    • 0030981562 scopus 로고    scopus 로고
    • Lipase-catalyzed chemoselective N-acylation of amino-sugar derivatives in hydrophobic solvent: Acid-amine ion-pair effects
    • Maugard T, Remeaud-Simeon M, Petre D, Monsan P. 1997b. Lipase-catalyzed chemoselective N-acylation of amino-sugar derivatives in hydrophobic solvent: Acid-amine ion-pair effects. Tetrahedron 53: 7587-7594.
    • (1997) Tetrahedron , vol.53 , pp. 7587-7594
    • Maugard, T.1    Remeaud-Simeon, M.2    Petre, D.3    Monsan, P.4
  • 33
    • 0030765316 scopus 로고    scopus 로고
    • Lipase-catalysed production of N-oleoyltaurine sodium salt in nonaqueous medium
    • Maugard T, Remeaud-Simeon M, Petre D, Monsan P. 1997c. Lipase-catalysed production of N-oleoyltaurine sodium salt in nonaqueous medium. Biotechnol Lett 19:751-753.
    • (1997) Biotechnol Lett , vol.19 , pp. 751-753
    • Maugard, T.1    Remeaud-Simeon, M.2    Petre, D.3    Monsan, P.4
  • 34
    • 0032530944 scopus 로고    scopus 로고
    • Enzymatic amidification for the synthesis of biodegradable surfactants: Synthesis of N-acylated hydroxylated amines
    • Maugard T, Remeaud-Simeon M, Petre D, Monsan P. 1998a. Enzymatic amidification for the synthesis of biodegradable surfactants: synthesis of N-acylated hydroxylated amines. J Mol Catal B: Enzymes 5:13-17.
    • (1998) J Mol Catal B: Enzymes , vol.5 , pp. 13-17
    • Maugard, T.1    Remeaud-Simeon, M.2    Petre, D.3    Monsan, P.4
  • 35
    • 0032497415 scopus 로고    scopus 로고
    • Kinetic study of chemoselective acylation of amino-alditol by immobilized lipase in organic solvent: Effect of substrate ionization
    • Maugard T, Remeaud-Simeon M, Monsan P. 1998b. Kinetic study of chemoselective acylation of amino-alditol by immobilized lipase in organic solvent: Effect of substrate ionization. Biochim Biophys Acta 1387:177-183.
    • (1998) Biochim Biophys Acta , vol.1387 , pp. 177-183
    • Maugard, T.1    Remeaud-Simeon, M.2    Monsan, P.3
  • 36
    • 33845185380 scopus 로고
    • Synthesis and therapeutic potential of hydroxamic acid based siderophores and analogs
    • Miller MJ. 1989. Synthesis and therapeutic potential of hydroxamic acid based siderophores and analogs. Chem Rev 89:1563-1579.
    • (1989) Chem Rev , vol.89 , pp. 1563-1579
    • Miller, M.J.1
  • 38
    • 0040522437 scopus 로고
    • Photoelectron stectroscopy study of hydrazine
    • Osafune K, Katsumate S, Kimura K. 1973. Photoelectron stectroscopy study of hydrazine. Chem Phys Lett 19:369-372.
    • (1973) Chem Phys Lett , vol.19 , pp. 369-372
    • Osafune, K.1    Katsumate, S.2    Kimura, K.3
  • 42
    • 0029883864 scopus 로고    scopus 로고
    • The mechanistic dissection of the plunge in enzymatic activity upon transition from water to anhydrous solvents
    • Schmittke JL, Wescott CR, Klibanov AM. 1996. The mechanistic dissection of the plunge in enzymatic activity upon transition from water to anhydrous solvents. J Am Chem Soc 118:3360-3365.
    • (1996) J Am Chem Soc , vol.118 , pp. 3360-3365
    • Schmittke, J.L.1    Wescott, C.R.2    Klibanov, A.M.3
  • 45
    • 0022551360 scopus 로고
    • Acyltransferase activity of the wide spectrum amidase of Brevibacterium sp. R312
    • Thiéry A, Maestracci M, Arnaud A, Galzy P. 1986. Acyltransferase activity of the wide spectrum amidase of Brevibacterium sp. R312. J Gen Microbiol 132:2205-2208.
    • (1986) J Gen Microbiol , vol.132 , pp. 2205-2208
    • Thiéry, A.1    Maestracci, M.2    Arnaud, A.3    Galzy, P.4
  • 46
    • 0025857486 scopus 로고
    • Lipase-catalyzed synthesis of n-octyl-alkyl amides in organic media
    • Tuccio B, Ferre E, Comeau L. 1991 Lipase-catalyzed synthesis of n-octyl-alkyl amides in organic media. Tetrahedron Lett 32:2763-2764.
    • (1991) Tetrahedron Lett , vol.32 , pp. 2763-2764
    • Tuccio, B.1    Ferre, E.2    Comeau, L.3
  • 47
    • 0032530927 scopus 로고    scopus 로고
    • Transeslerification of lactulose with ethyl butanoate catalysed by Candida antarctica lipase
    • Van der Heijden AM, Zuijderduijn FJ, Van Rantwijk F. 1998. Transeslerification of lactulose with ethyl butanoate catalysed by Candida antarctica lipase. J Mol Catal A: Chem 134:259-65.
    • (1998) J Mol Catal A: Chem , vol.134 , pp. 259-265
    • Van Der Heijden, A.M.1    Zuijderduijn, F.J.2    Van Rantwijk, F.3
  • 48
    • 77957073549 scopus 로고    scopus 로고
    • Stabilisation of lipases for activity in ammoniolysis
    • Ballasteros A, Plou FJ, Iborra JL, Halling P, editors. Amsterdam: Elsevier Science
    • Van Rantwijk F, Kock-van Dalen AC, Sheldon RA. 1998. Stabilisation of lipases for activity in ammoniolysis. In: Ballasteros A, Plou FJ, Iborra JL, Halling P, editors. Stability and stabilisation of enzymes. Amsterdam: Elsevier Science. p 447-452.
    • (1998) Stability and Stabilisation of Enzymes , pp. 447-452
    • Van Rantwijk, F.1    Kock-Van Dalen, A.C.2    Sheldon, R.A.3
  • 49
    • 0342762034 scopus 로고    scopus 로고
    • Fatty hydroxamic acid biosynthesis in aqueous medium in the presence of the lipase-acyltransferase from Candida parapsilosis
    • Vaysse L, Debreucq E, Pirat JL, Galzy P. 1997. Fatty hydroxamic acid biosynthesis in aqueous medium in the presence of the lipase-acyltransferase from Candida parapsilosis. J Biotechnol 53:41-46.
    • (1997) J Biotechnol , vol.53 , pp. 41-46
    • Vaysse, L.1    Debreucq, E.2    Pirat, J.L.3    Galzy, P.4
  • 51
    • 0030569896 scopus 로고    scopus 로고
    • Regioselective acylation of disaccharides in ten-butyl alcohol catalyzed by Candida antarctica lipase
    • Woudenberg-van Oosterom M, Van Rantwijk F, Sheldon RA. 1996. Regioselective acylation of disaccharides in ten-butyl alcohol catalyzed by Candida antarctica lipase. Biotechnol Bioeng 49:328-333.
    • (1996) Biotechnol Bioeng , vol.49 , pp. 328-333
    • Woudenberg-Van Oosterom, M.1    Van Rantwijk, F.2    Sheldon, R.A.3
  • 52
    • 0000321692 scopus 로고
    • Enzyme-catalyzed processes in organic solvents
    • Zaks A, Klibanov AM. 1985. Enzyme-catalyzed processes in organic solvents. Proc Natl Acad Sci USA 82:3192-3196.
    • (1985) Proc Natl Acad Sci USA , vol.82 , pp. 3192-3196
    • Zaks, A.1    Klibanov, A.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.