메뉴 건너뛰기




Volumn 11, Issue 2, 1999, Pages 109-114

Enantioselective hydrolysis of 1-butyryloxyalkylphosphonates by lipolytic microorganisms: Pseudomonas fluorescens and Penicillium citrinum

Author keywords

Biotransformation; Enantioselectivity; Es ter hydrolysis; Hydroxyphosphonates; Lipases

Indexed keywords

1 HYDROXY 1 PHENYLMETHYLPHOSPHONIC ACID DIETHYL ESTER; 1 HYDROXYPENTYLPHOSPHONIC ACID DIETHYL ESTER; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032895010     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:2<109::AID-CHIR5>3.0.CO;2-T     Document Type: Article
Times cited : (23)

References (24)
  • 1
    • 0027238038 scopus 로고
    • Enantioselective lipase-catalyzed ester hydrolysis: Effect on rates and enantioselectivity from a variation of ester structure
    • Bojarski J, Oxelbark J, Andersson C, Allenmark S. Enantioselective lipase-catalyzed ester hydrolysis: effect on rates and enantioselectivity from a variation of ester structure. Chirality 1993;5:154-158.
    • (1993) Chirality , vol.5 , pp. 154-158
    • Bojarski, J.1    Oxelbark, J.2    Andersson, C.3    Allenmark, S.4
  • 2
    • 37049088013 scopus 로고
    • Resolution of mandelic acid by lipase-catalysed transesterifications in organic media: Inversion of enantioselectivity mediated by acyl donor
    • For example see (a) Miyazawa T, Kurita S, Ueji S, Yamada T, Kuwata S. Resolution of mandelic acid by lipase-catalysed transesterifications in organic media: inversion of enantioselectivity mediated by acyl donor. J Chem Soc Perkin Trans 1992;1:2253-2255;
    • (1992) J Chem Soc Perkin Trans , vol.1 , pp. 2253-2255
    • Miyazawa, T.1    Kurita, S.2    Ueji, S.3    Yamada, T.4    Kuwata, S.5
  • 3
    • 0027594761 scopus 로고
    • Lipase-catalysed transesterification in organic solvents: Applications to the preparation of enantiomerically pure compounds
    • (b) Santaniello E, Ferraboschi P, Grisenti P. Lipase-catalysed transesterification in organic solvents: applications to the preparation of enantiomerically pure compounds. Enzyme Microb Technol 1993;15:367-382;
    • (1993) Enzyme Microb Technol , vol.15 , pp. 367-382
    • Santaniello, E.1    Ferraboschi, P.2    Grisenti, P.3
  • 4
    • 0029960472 scopus 로고    scopus 로고
    • Kinetic resolution of amino acid ester catalyzed by lipases
    • (c) Houng J, Wu M, Chen S. Kinetic resolution of amino acid ester catalyzed by lipases. Chirality 1996;8:418-422.
    • (1996) Chirality , vol.8 , pp. 418-422
    • Houng, J.1    Wu, M.2    Chen, S.3
  • 6
    • 0030988373 scopus 로고
    • S-1-(3-Hydroxy-2-phosphonylmetoxypropyl)cytosine (HPMPC) inhibits HIV-1 replication in epithelial cells, but not T-lymphocytes
    • Srinivas R, Connely M, Fridland A. (S)-1-(3-Hydroxy-2-phosphonylmetoxypropyl)cytosine (HPMPC) inhibits HIV-1 replication in epithelial cells, but not T-lymphocytes. Antiviral Res 1007;35:23-27.
    • (1007) Antiviral Res , vol.35 , pp. 23-27
    • Srinivas, R.1    Connely, M.2    Fridland, A.3
  • 7
    • 0024987959 scopus 로고
    • Preparation of peptidic α-hydroxy phosphonates: A new class of transition state analog renin inhibitors
    • (a) Patel D, Rielly-Gauvin K, Ryono, D. Preparation of peptidic α-hydroxy phosphonates: a new class of transition state analog renin inhibitors. Tetrahedron Lett 1990a;31:5587-5590;
    • (1990) Tetrahedron Lett , vol.31 , pp. 5587-5590
    • Patel, D.1    Rielly-Gauvin, K.2    Ryono, D.3
  • 8
    • 0025041777 scopus 로고
    • Peptidic α-hydroxy phosphinyls C-terminal modification methodology
    • (b) Patel D, Rielly-Gauvin K, Ryono D. Peptidic α-hydroxy phosphinyls C-terminal modification methodology. Tetrahedron Lett 1990b;31:5591-1994.
    • (1990) Tetrahedron Lett , vol.31 , pp. 5591-11994
    • Patel, D.1    Rielly-Gauvin, K.2    Ryono, D.3
  • 10
    • 0030832116 scopus 로고    scopus 로고
    • Inhibitors directed towards the binuclear metal center of phosphotriesterase
    • Hong S, Raushel F. Inhibitors directed towards the binuclear metal center of phosphotriesterase. J Enzyme Inhib 1997;12:191-203.
    • (1997) J Enzyme Inhib , vol.12 , pp. 191-203
    • Hong, S.1    Raushel, F.2
  • 11
    • 0001060249 scopus 로고
    • The absolute configuration of α-hydroxyphosphonates
    • Smardijk A, Noorda S, Bolhuis F, Wynberg H. The absolute configuration of α-hydroxyphosphonates. Tetrahedron Lett 1985;26:493-496; Hoffmann M. Optically active 1-hydroxy-3-methylbutanephosphonic acid and its derivatives. J Prakt Chem 1990;332:251-255.
    • (1985) Tetrahedron Lett , vol.26 , pp. 493-496
    • Smardijk, A.1    Noorda, S.2    Bolhuis, F.3    Wynberg, H.4
  • 12
    • 0001060249 scopus 로고
    • Optically active 1-hydroxy-3-methylbutanephosphonic acid and its derivatives
    • Smardijk A, Noorda S, Bolhuis F, Wynberg H. The absolute configuration of α-hydroxyphosphonates. Tetrahedron Lett 1985;26:493-496; Hoffmann M. Optically active 1-hydroxy-3-methylbutanephosphonic acid and its derivatives. J Prakt Chem 1990;332:251-255.
    • (1990) J Prakt Chem , vol.332 , pp. 251-255
    • Hoffmann, M.1
  • 14
    • 0029813748 scopus 로고    scopus 로고
    • Enzymes in organic chemistry, part 4: Enantioselective hydrolysis of 1-acyloxy(aryl)methyl and 1-acyloxy(heteroaryl)phosphonates with lipases from Aspergillus niger and Rhizopus oryzae. A comparative study
    • For example see (a) Eidenhammer G, Hammerschmidt F. Enzymes in organic chemistry, Part 4: enantioselective hydrolysis of 1-acyloxy(aryl)methyl and 1-acyloxy(heteroaryl)phosphonates with lipases from Aspergillus niger and Rhizopus oryzae. A comparative study. Synthesis 1996;748-754;
    • (1996) Synthesis , pp. 748-754
    • Eidenhammer, G.1    Hammerschmidt, F.2
  • 15
    • 0030937175 scopus 로고    scopus 로고
    • Stereoselective acetylation of [1-(hydroxy)-4-(3-phenyl)butyl]phosphonic acid, diethyl ester
    • (b) Patel R, Banerjaa A, Szarka L. Stereoselective acetylation of [1-(hydroxy)-4-(3-phenyl)butyl]phosphonic acid, diethyl ester. Tetrahedron Asymmetry 1997;8:1055-1059.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 1055-1059
    • Patel, R.1    Banerjaa, A.2    Szarka, L.3
  • 16
    • 0027426916 scopus 로고
    • Whole cell biocatalysis in nonconventional media
    • Nikolova P, Ward O. Whole cell biocatalysis in nonconventional media. J Ind Microbiol 1993;12:76-86.
    • (1993) J Ind Microbiol , vol.12 , pp. 76-86
    • Nikolova, P.1    Ward, O.2
  • 17
    • 0001097742 scopus 로고
    • An unexpected reactivity of simple heterogeneous mixture of γ-alumina and potassium fluoride: 1-hydroxyalkane phosphonic esters synthesis from non-activated ketones in 'dry media.'
    • Texier-Boullet F, Lequitte M. An unexpected reactivity of simple heterogeneous mixture of γ-alumina and potassium fluoride: 1-hydroxyalkane phosphonic esters synthesis from non-activated ketones in 'dry media.' Tetrahedron Lett 1986;27:3515-3516.
    • (1986) Tetrahedron Lett , vol.27 , pp. 3515-3516
    • Texier-Boullet, F.1    Lequitte, M.2
  • 18
    • 0026832773 scopus 로고
    • Production and some properties of lipase from Penicillium citrinum
    • (a) Maliszewska I, Mastalerz P. Production and some properties of lipase from Penicillium citrinum. Enzyme Microb Technol 1992;14: 190-193;
    • (1992) Enzyme Microb Technol , vol.14 , pp. 190-193
    • Maliszewska, I.1    Mastalerz, P.2
  • 19
    • 85007771950 scopus 로고
    • The effect of culture conditions on lipolytic productivity of microorganisms
    • (b) Sztajer H, Maliszewska I, Wieczorek J. The effect of culture conditions on lipolytic productivity of microorganisms. Enzyme Microb Technol 1988;10:395-400.
    • (1988) Enzyme Microb Technol , vol.10 , pp. 395-400
    • Sztajer, H.1    Maliszewska, I.2    Wieczorek, J.3
  • 23
    • 0026768324 scopus 로고
    • Organophosphonate utilization by the wild-type strain of pseudomonas fluorescens
    • Zboińska E, Lejczak B, Kafarski P. Organophosphonate utilization by the wild-type strain of Pseudomonas fluorescens. Appl Environ Microbiol 1992;58:2993-2999.
    • (1992) Appl Environ Microbiol , vol.58 , pp. 2993-2999
    • Zboińska, E.1    Lejczak, B.2    Kafarski, P.3
  • 24
    • 0028019445 scopus 로고
    • Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalysed borane reduction of diethyl α-ketophosphonates
    • Gajda T. Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalysed borane reduction of diethyl α-ketophosphonates. Tetrahedron Asymmetry 1994;5:1965-1972.
    • (1994) Tetrahedron Asymmetry , vol.5 , pp. 1965-1972
    • Gajda, T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.