Browse > Article

Functional Analyses and Application of Microbial Lactonohydrolases  

Shimizu, Sakayu (Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University)
Honda, Kohsuke (Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University)
Kataoka, Michihiko (Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University)
Publication Information
Biotechnology and Bioprocess Engineering:BBE / v.7, no.3, 2002 , pp. 130-137 More about this Journal
Abstract
Microbial lactonohydrolases (intramolecular ester bond-hydrolyzing enzymes) with unique properties were found. The lactonohydrolase from Fusarium oxysporum catalyzes enantiose-lective hydrolysis of aldonate lactones and D-pantoyl lactone (D-PL). This enzyme is useful for the large-scale optical resolution of racemic PL. The Agrobacterium tumefaciens enzyme catalyzes asymmetric hydrolysis of PL, but the stereospecificity is opposite to that of the Fusarium enzyme. Dihydrocoumarin hydrolase (DHase) from Acinetobacter calcoaceticus is a bifunctional enzyme, which catalyzes not only hydrolysis of aromatic lactones but also bromination of monochlorodi-medon in the presence of H$_2$O$_2$and dihydrocoumarin. DHase also hydrolyzes several linear esters, and is useful for enantioselective hydrolysis of methyl DL-$\beta$-acetylthioisobutyrate and regioselective hydrolysis of methyl cetraxate.
Keywords
lactonohydrolase; lactone; stereospecific hydrolysis; resioselective hydrolysis;
Citations & Related Records

Times Cited By SCOPUS : 2
연도 인용수 순위
1 /
[ Patel, R. N.(ed.) ] / Stereoselective biocatalysis.
2 Pantothenic acid and related compounds /
[ Shimizu, S.;M. Kataoka;M. C. Flickinger(ed.);S. W. Drew(ed.) ] / Encyclopedia of Bioprocess Technology: Fermentation, Biocatalysis, and Bioseparation
3 /
[ Ollis, D. L.;E. Cheah;M. Cygler;B. Dijkstra;E. Frolow;S. M. Franken;M. Harel;S. J. Remington;I. Silman;J. Schrag;J. L. Sussman;K. H. G. Verschueren;A. Goldman ] / The α/β hydrolase fold. Protein Eng.
4 NADH-dependent halogenases are more likely to be involved in halometabolite biosynthesis than haloperoxidases /
[ Hohaus, K.;A. Altmannm;W. Burd;I. Fischer;P. E. Hammer;D. S. Hill;J. M. Ligon;K.-H. van Pee ] / Angew. Chem. Int. Ed. Engl.   DOI   ScienceOn
5 Human serum paraoxonase (PON1) isozymes Q and R hydrolyze lactones and cyclic carbonate esters /
[ Billecke, S.;D. Draganov;R. Counsell;P. Stetson;C. Watson;C. Hsu;B. N. La Du ] / Drug Metab. Dispos.
6 Purification and properties of an enzyme in human blood and rat liver microsomes catalyzing the formation and hydrolysis of r-lactones /
[ Fishbein, W. N.;S. P. Bessman ] / J. Biol. Chem.
7 The Streptomyces peucetius dpsY and dnrX genes govern early and late steps of daunorubicin and doxorubicin biosynthesis /
[ Lomovdkaya, N.;Y. Doi-Katayam;S. Filippini;C. Nastro;L. Fonstein;M. Gallo;A. L. Colombo;C. R. Hutchinson ] / J. Bacteriol.
8 Optical resolution of racemic pantolactone with a novel fungal enzyme, lactonohydrolase /
[ Kataoka, M.;K. Shimizu;K. Sakamoto;H. Yamada;S. Shimizu ] / Appl. Microbiol. Biorechnol   DOI
9 The role of aldonolactonase in the conversion of L-gulonate to L-ascorbate /
[ Bulitz, C.;A. Lehninger ] / Biochim. Biophys. Acta   DOI   ScienceOn
10 On the microsomal and soluble lactonases /
[ Yamada, K.;S. Ishikawa;N. Shimazono ] / Biochim. Biophys. Acta   DOI   ScienceOn
11 Chloroperoxidase from Streptomyces lividans: Isolation and characterization of the enzyme and the corresponding gene /
[ Bantleon, R.;J. Altenbuchner;K.-H. van Pee ] / J. Bacteriol.   DOI
12 Lactonohydrolase-catalyaed optical resolution of pantoyl lactone: selection of a potent producer and optimization of culture and reaction conditions for practical resolution /
[ Kataoka, M.;K. Shimizu;K. Sakamoto;H. Yamada;S. Shimizu ] / Appl. Microbiol. Biotechnol.   DOI   ScienceOn
13 Cloning and nucleotide sequence of an esterase gene /
[ Choi, K. D.;G. H. Jeohn;J. S. Rhee;O. J. Yoo ] / Pseudomonas fluorescens and expression of the gene in Escherichia coli. Agric. Biol. Chem.
14 Thiocarbamate herbicide-inducible nonheme haloperoxidase of Rhodococcus erythropolis NI86/21. /
[ De Schrijver, A.;I. Nagy;G. Schoofs;P. Proost;J. Vanderleyden;K.-H. van Pee;R. De Mot ] / Appl. Environ. Microbiol.
15 Studies on glucuronolactonase and gulonolactonase /
[ Yamada, K. ] / J. Biochem.   DOI
16 The oxidation of L-arabinose /
[ Weimberg, R.;M. Doudoroff ] / Pseudomonas saccharophila. J. Biol. Chem.
17 Microbial lipases in the biocatalysis /
[ Ortaggi, G.;K.-E. Jaeger(eds.) ] / J. Molec. Catalysis B: Enzymatic 3
18 Purification and characterization of a novel lactonohydrolase, catalyzing the hydrolysis of aldonate lactones and aromatic lactones /
[ Shimizu, S.;M. Kataoka;K. Shimizu;M. Hirakata;K. Sakamoto;H. Yamada ] / Fusatium oxysporum. Purification and characterizetion. Eur. J. Biochem
19 Microbial resolution of O-acetyl pantoyl lactone /
[ Glanzer, B. I.;K. Faber;H. Griengl ] / Enzyme Microb. Technol.   DOI   ScienceOn
20 3,4-Dihydrocoumarin hydrolase with haloperoxidase acitvity /
[ Kataoka, M.;K. Honda;S. Shimizu ] / Acinetobacter calcoaceticus F46. Eur. J. Biochem.
21 Synthesis of captopril starting from an optically active β-hydroxy acid /
[ Shimazaki, M.;J. Hasegawa;K. Kan;K. Nomura;Y. Nose;H. Kondo;T. Ohashi;K. Watanabe ] / Chem. Pharm. Bull.   DOI
22 A bacterial esterase is homologous with non-haem haloperoxidases and displays brominating activity /
[ Pelletier, I.;J. Altenbuchner ] / Microbiology   DOI   ScienceOn
23 Cloning of a second non-haem bromoperoxidase gene from Streptomyces sureofaciens ATCC 10762: Sequence analysis, expression in Streptomyces lividens and enzyme purification /
[ Pelletier, I.;O. Pfeifer;J. Altenbuchner;K.-H. van Pee ] / Microbiology   DOI   ScienceOn
24 Aldono-and uronolactonases of animal tissues /
[ Winkelman, J.;A. L. Lehninger ] / J. Biol. Chem.
25 Partial purification, and some properties and reactivites of cetraxate benzyl ester hydrochloride-hydrolyzing enzyme. /
[ Kuroda, H.;A. Miyadera;A. Imura;A. Suzuki ] / Chem. Pharm. Bull.   DOI   ScienceOn
26 Inhibition of the renin-angiotensin system: A new approach to the therapy of hypertension /
[ Ondetti, M. A.;D. W. Cushman ] / J. Med. Chem.   DOI
27 Analysis of two chromosomal regions adjacent to genes for a type II polyketide synthase involved in the biosynthesis of the antitumor polyketide mithramycin /
[ Prado, L.;F. Lombo;A. F. Brana;C. Mendez;J. Rohr;J.A. Salas ] / Streptomyces argillaceus. Mol. Gen. Genet.   DOI   ScienceOn
28 Purification and characterization of a novel lactonohydrolase /
[ Kataoka, M.;J. Nomura;K. Nose;M. Shinohara;S. Shimizu ] / Agrobacterium tumefaciens. Biosci. Biotechnol. Biochem.   DOI   ScienceOn
29 Rabbit serum paraoxonase 3 (PON3) is a high density lipoprotein-associated lactonase and protects low density lipoprotein against oxidation /
[ Draganov, D. I.;P. L. Stetson;C. E. Watson;S. S. Billecke;B. N. La Du ] / J. Biol. Chem.   DOI   ScienceOn
30 Vitamins and related compounds: microbial production /
[ Shimizu, S.;G. Reed(ed.);H.-J. Rehm (ed.) ] / Biotechnology,
31 Comparative studies on soluble lactonases /
[ Kawada, M.;H. Takiguchi;Y. Kagawa;K. Suzuki;N. Shimazono ] / J. Biochem.   DOI
32 Glucono-8-lactone /
[ Hucho, F.;K. Wallenfels ] / Escherichia coli. Biochim. Biophys. Acta   DOI   ScienceOn
33 Nucleotide sequence of the gene for a thermostable esterase /
[ Ozaki, E.;A. Sakimae;R. Numazawa ] / Pseudomonas putida MR-2068. Biosci. Biotechnol. Biochem.   DOI   ScienceOn
34 Screening of microorganisms producing D-β-acetylthioisobutyric acid from methyl DL-β-acetylthioisobutyrate /
[ Sakimae, A.;A. Hosoi;E. Kobayashi;N. Ohsuga;R. Numazawa;I. Watanabe;H. Ohnishi ] / Biosci. Biotechnol. Biochem.   DOI
35 Chloroperoxidase-encoding gene from Pseudomonas pyrrocinica: Sequence, expression in heterologous hosts, and purification of the enzyme /
[ Wolffram, C.;F. Lingens;R. Mutzel;K.-H. van Pee ] / Gene   DOI   ScienceOn
36 Metal-free haloperoxidases: Fact or artifact? /
[ Kirk, O.;L. S. Conrad ] / Angew. Chem. Int. Ed. Engl.   DOI   ScienceOn
37 Metabolism of carbohydrates /
[ Palleroni, N. J.;M. Doudorof ] / Pseudomonas saccharophila. J. Bacteriol
38 The metabolism of aromatic compounds in higher plants /
[ Kosuge, T.;E. E. Conn ] / J. Biol. Chem.
39 /
[ Kataoka, M.;K. Honda;S. Shimizu ] / Dihydrocoumarin hydrolase from Acinetobacter calcoaceticus F46 Functional analysis and applications. Abstracts of the 5th International Symposium of Biocatalysis and Biotransformation
40 Optical resolution of racemic pantoic acid through microbial stereoselective lactonization in an organic solvent/water two-phase system /
[ Kataoka, M.;M. Hirakata;K. Sakamoto;H. Yamada;S. Shimizu ] / Enzyme Microb. Technol.   DOI   ScienceOn
41 Process conditions for the production of D-β-acetylthioisobutyric acid from methyl DL-β-acetylthioisobutyrate with the cells of Pseudomonas putida MR-2068 /
[ Sakimae, A.;E. Ozaki;H. Toyama;N. Ohsuga;R. Numazawa;I. Muraoka;E. Hamada;H. Ohnishi ] / Biosci. Biotechnol. Biochem.   DOI
42 Oxidative pathway for L-rhamnose degradation in /
[ Rigo, L. U.;L. R.;Marechal;M. M. Vieira;L. A. Veiga ] / Pullularia pullulans. Can. J. Microbiol   DOI
43 Proceedings of the 3rd International Symposium on Biocatalysis and Biotransformations /
[ Azerad, R.(ed.) ] / J. Molec. Catalysis B: Enzymatic 5.
44 Biosynthesis of halogenated metabolites by bacteria /
[ van Pee, K.-H. ] / Annu. Rev. Microbiol.   DOI   ScienceOn
45 Isolation and characterization of the gene encoding gluconolactonase /
[ Kanagasundaram, V.;R. Scopes ] / Zymomonas mobilis. Biochim. Biophys. Acta   DOI   ScienceOn
46 The role of xylonolactone in xylonic acid production /
[ Buchert, J.;L. Viikari ] / Pseudomonas fragi. Appl. Microbiol. Biotechnol
47 Purification and characterization of a novel esterase promising for the production of useful compounds from Microbacterium sp. 7-1 /
[ Honda, K.;M. Kataoka;H. Ono;K. Sakamoto;S. Kita;S. Shimizu ] / W. FEMS Microbiol. Lett.   DOI   ScienceOn
48 Lipase catalysis in organic solvents; transesterification of O-formyl esters of secondary alcohols /
[ Bevinakatti, H. S.;R. V. Newadkar ] / Biotechnol. Lett.   DOI
49 Screening, nucleotide sequence, and biological characterization of an esterase /
[ Khalameyzer, V.;I. Fischer;U. T. Bornscheuer;J. Altenbuchner ] / Pseudomonas fluorescens with high activity towards lactones. Appl. Environ. Microbiol.
50 Characterization of cDNA clones encoding rabbit and human serum paraoxonase: the mature protein retains its signal sequence /
[ Hassett, C.;R. J. Richter;R. Humbert;C. Chapline;J. W. Crabb;C. J. Omiecinski;C. E. Furlong ] / Biochemistry   DOI   ScienceOn
51 Molecular cloning and sequencing of a non-heam bromoperoxidase gene /
[ Pfeifer, O.;I. Pelletier;J. Altenbuchner;K.-H. van Pee ] / Streptomyces aureofaciens ATCC 10762. J. Gen. Microbiol.
52 Lactone-ring-cleaving enzyme: genetic analysis, RNA edting, and evolutionary implications /
[ Kobayashi, M.;M. Shinohara;C. Sakoh;M. Kataoka;S. Shimizu ] / Proc. Natl. Acad. Sci.   DOI   ScienceOn