{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,21]],"date-time":"2026-05-21T06:44:03Z","timestamp":1779345843824,"version":"3.51.4"},"publisher-location":"Totowa, NJ","reference-count":49,"publisher":"Humana Press","isbn-type":[{"value":"9781617793301","type":"print"},{"value":"9781617793318","type":"electronic"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2012]]},"DOI":"10.1007\/978-1-61779-331-8_3","type":"book-chapter","created":{"date-parts":[[2011,9,28]],"date-time":"2011-09-28T16:48:55Z","timestamp":1317228535000},"page":"37-54","source":"Crossref","is-referenced-by-count":3,"title":["Enzymatic Production of Enantiopure Amino Acids from Mono-substituted Hydantoin Substrates"],"prefix":"10.1007","author":[{"given":"Gwynneth F.","family":"Matcher","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rosemary A.","family":"Dorrington","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Stephanie G.","family":"Burton","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"297","published-online":{"date-parts":[[2011,8,26]]},"reference":[{"key":"3_CR1_3","doi-asserted-by":"publisher","first-page":"513","DOI":"10.1016\/S1359-6446(97)01078-7","volume":"2","author":"A Zaks","year":"1997","unstructured":"Zaks A and Dodds DR (1997) Application of biocatalysis and biotransformations to the synthesis of pharmaceuticals. Drug Discovery Today 2, 513\u2013531.","journal-title":"Drug Discovery Today"},{"key":"3_CR2_3","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/S1381-1177(98)00009-5","volume":"5","author":"AS Bommarius","year":"1998","unstructured":"Bommarius AS, Schwarm M and Drauz K (1998) Biocatalysis to amino acid-based chiral pharmaceuticals \u2013 examples and perspectives. J Mol Catal B Enzym 5, 1\u201311.","journal-title":"J Mol Catal B Enzym"},{"key":"3_CR3_3","doi-asserted-by":"publisher","first-page":"3","DOI":"10.1016\/S0021-9673(00)00532-X","volume":"906","author":"NM Maier","year":"2001","unstructured":"Maier NM, Franco P and Lindner W (2001) Separation of enantiomers: needs, challenges, perspectives. J Chromatogr A 906, 3\u201333.","journal-title":"J Chromatogr A"},{"key":"3_CR4_3","doi-asserted-by":"publisher","first-page":"232","DOI":"10.1038\/35051706","volume":"409","author":"KM Koeller","year":"2001","unstructured":"Koeller KM and Wong C (2001) Enzymes for chemical synthesis. Nature 409, 232\u2013240.","journal-title":"Nature"},{"key":"3_CR5_3","first-page":"17","volume":"132","author":"R Azerad","year":"1995","unstructured":"Azerad R (1995) Application of biocatalysis in organic synthesis. Bull Soc Chim Fr 132, 17\u201351.","journal-title":"Bull Soc Chim Fr"},{"key":"3_CR6_3","doi-asserted-by":"publisher","first-page":"559","DOI":"10.1016\/S0958-1669(01)00263-4","volume":"12","author":"J Altenbuchner","year":"2001","unstructured":"Altenbuchner J, Siemann-Herzberg M and Syldatk C. (2001) Hydantoinases and related enzymes as biocatalysts for the synthesis of unnatural chiral amino acids. Curr Opin Biotechnol 12, 559\u2013563.","journal-title":"Curr Opin Biotechnol"},{"key":"3_CR7_3","doi-asserted-by":"publisher","first-page":"258","DOI":"10.1038\/35051736","volume":"409","author":"A Schmid","year":"2001","unstructured":"Schmid A, Dordick JS, Hauer B, et al. (2001) Industrial biocatalysis today and tomorrow. Nature 409, 258\u2013268.","journal-title":"Nature"},{"key":"3_CR8_3","doi-asserted-by":"publisher","first-page":"157","DOI":"10.1016\/S0957-4166(01)00028-3","volume":"12","author":"R Smith","year":"2001","unstructured":"Smith R, Pietzsch M, Waniek T, et al. (2001) Enzymatic synthesis of enantiomerically enriched D- and L-3-silated alanines by deracemization of DL-5-silylmethylated hydantoins. Tetrahedron: Asymmetry 12, 157\u2013165.","journal-title":"Tetrahedron: Asymmetry"},{"key":"3_CR9_3","doi-asserted-by":"publisher","first-page":"801","DOI":"10.1007\/s002530051594","volume":"52","author":"J Ogawa","year":"1999","unstructured":"Ogawa J, Ryono A, Xie S, et al. (1999) \u03b2-carbon stereoselectivity of N-carbamoyl-D-\u03b1-amino acid amidohydrolase for \u03b1,\u03b2-diastereomeric amino acids. Appl Microbiol Biotechnol 52, 801.","journal-title":"Appl Microbiol Biotechnol"},{"key":"3_CR10_3","doi-asserted-by":"publisher","first-page":"711","DOI":"10.1023\/A:1005592615103","volume":"21","author":"J Ogawa","year":"1999","unstructured":"Ogawa J, Ryono A, Xie S, et al. (1999) Simultaneous recognition of two chiral centres in \u03b1,\u03b2-diastereomeric amino acids by an N-carbamoyl-L-\u03b1-amino acid amidohydrolase from Alcaligenes xylosoxidans. Biotechnol Lett 21, 711\u2013713.","journal-title":"Biotechnol Lett"},{"key":"3_CR11_3","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1016\/S1381-1177(00)00205-8","volume":"12","author":"J Ogawa","year":"2001","unstructured":"Ogawa J, Ryono A, Xie S, et al. (2001) Separative preparation of the four stereoisomers of \u03b2-methylphenylalanine with N-carbamoyl amino acid amidohydrolases. J Mol Catal B Enzym 12, 71\u201375.","journal-title":"J Mol Catal B Enzym"},{"key":"3_CR12_3","doi-asserted-by":"publisher","first-page":"293","DOI":"10.1007\/s002530051395","volume":"51","author":"C Syldatk","year":"1999","unstructured":"Syldatk C, May O, Altenbuchner J, et al. (1999) Microbial hydantoinases \u2013 industrial enzymes from the origin of life? Appl Microbiol Biotechnol 51, 293\u2013309.","journal-title":"Appl Microbiol Biotechnol"},{"key":"3_CR13_3","doi-asserted-by":"publisher","first-page":"367","DOI":"10.1016\/S0958-1669(02)00331-2","volume":"13","author":"J Ogawa","year":"2002","unstructured":"Ogawa J and Shimizu S (2002) Industrial microbial enzymes: their discovery by screening and use in large-scale production of useful chemicals in Japan. Curr Opin Biotechol 13, 367\u2013375.","journal-title":"Curr Opin Biotechol"},{"key":"3_CR14_3","doi-asserted-by":"publisher","first-page":"345","DOI":"10.1016\/0168-1656(90)90118-U","volume":"14","author":"C Syldatk","year":"1990","unstructured":"Syldatk C, Mackowiak V, Hoke H, et al. (1990) Cell growth and enzyme synthesis of a mutant of Arthrobacter sp. (DSM 3747) used for the production of L-amino acids from D,L-5- monosubstituted hydantoins. J Biotechnol 14, 345\u2013362.","journal-title":"J Biotechnol"},{"key":"3_CR15_3","unstructured":"Syldatk C and Pietzsch M (1995) Hydrolysis and formation of hydantoins. in Enzyme catalysis in organic synthesis \u2013 A comprehensive handbook. Vol. 1. Eds. Drauz K. & Waldmann H., VCH Publishers Inc. Weinheim, pp. 409\u2013431."},{"key":"3_CR16_3","doi-asserted-by":"crossref","unstructured":"Matcher GF (2004) Characterization of the hydantoin-hydrolysing system of Pseudomonas putida RU-KM3s. PhD Thesis, Rhodes University, South Africa.","DOI":"10.1007\/s00253-004-1597-3"},{"key":"3_CR17_3","volume-title":"Molecular Cloning \u2013 A laboratory manual","author":"J Sambrook","year":"1989","unstructured":"Sambrook J, Margolin A, Russell A and Klibanov A (1989) Molecular Cloning \u2013 A laboratory manual. Cold Spring Harbor Press, New York."},{"key":"3_CR18_3","doi-asserted-by":"publisher","first-page":"91","DOI":"10.1111\/j.1574-6968.2001.tb10503.x","volume":"195","author":"P Santos","year":"2001","unstructured":"Santos P, Bartolo I, Blatny J, et al. (2001) New broad-host-range promoter probe vectors based on the plasmid RK2 replicon. FEMS Microbiol Lett 195, 91\u201396.","journal-title":"FEMS Microbiol Lett"},{"key":"3_CR19_3","doi-asserted-by":"publisher","first-page":"401","DOI":"10.1111\/j.1749-6632.1996.tb33232.x","volume":"799","author":"DC Lee","year":"1996","unstructured":"Lee DC, Lee SG, Hong SP, et al. (1996) Cloning and overexpression of thermostable D-hydantoinase from thermophile in E. coli and its application to the synthesis of optically active D-amino acids. Ann N Y Acad Sci 799, 401\u2013405.","journal-title":"Ann N Y Acad Sci"},{"key":"3_CR20_3","doi-asserted-by":"publisher","first-page":"1039","DOI":"10.1021\/bp9901163","volume":"15","author":"YP Chao","year":"1999","unstructured":"Chao YP, Fu H, Lo TE, et al. (1999) One-step production of D-p-hydroxyphenylglycine by recombinant Escherichia coli strains. Biotechnol Prog 15, 1039\u20131045.","journal-title":"Biotechnol Prog"},{"key":"3_CR21_3","doi-asserted-by":"publisher","first-page":"882","DOI":"10.1271\/bbb.62.882","volume":"62","author":"Y Ikenaka","year":"1998","unstructured":"Ikenaka Y, Nanba H, Yamada Y, et al. (1998) Screening, characterization, and cloning of the gene for N-carbamyl-D-amino acid amidohydrolase from thermotolerant soil bacteria. Biosci Biotechol Biochem 62, 882\u2013886.","journal-title":"Biosci Biotechol Biochem"},{"key":"3_CR22_3","doi-asserted-by":"publisher","first-page":"1621","DOI":"10.1271\/bbb.58.1621","volume":"58","author":"Y Mukohara","year":"1994","unstructured":"Mukohara Y, Ishikawa T, Watabe K and Nakamura H (1994) A thermostable hydantoinase of Bacillus stearothermophilus NS1122A: Cloning, sequencing, and high expression of the enzyme gene, and some properties of the expressed enzyme. Biosci Biotechol Biochem 58, 1621\u20131626.","journal-title":"Biosci Biotechol Biochem"},{"key":"3_CR23_3","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/S0167-4781(97)00097-3","volume":"1395","author":"HR Chien","year":"1998","unstructured":"Chien HR, Jih Y, Yang W and Hsu W (1998) Identification of the open reading frame for the Pseudomonas putida D-hydantoinase gene and expression of the gene in Escherichia coli. Biochim Biophys Acta 1395, 68\u201377.","journal-title":"Biochim Biophys Acta"},{"key":"3_CR24_3","first-page":"55","volume":"145","author":"A Buson","year":"1996","unstructured":"Buson A, Negro A, Grassato L, et al. (1996) Identification, sequencing and mutagenesis of the gene for a D-carbamoylase from Agrobacterium radiobacter. FEMS Microbiol Lett 145, 55\u201362.","journal-title":"FEMS Microbiol Lett"},{"key":"3_CR25_3","doi-asserted-by":"publisher","first-page":"564","DOI":"10.1021\/bp0000611","volume":"16","author":"JH Park","year":"2000","unstructured":"Park JH, Kim GJ and Kim HS (2000) Production of D-amino acid using whole cells of recombinant Escherichia coli with separately and coexpressed D-hydantoinase and N-carbamoylase. Biotechnol Prog 16, 564\u2013570.","journal-title":"Biotechnol Prog"},{"key":"3_CR26_3","doi-asserted-by":"publisher","first-page":"689","DOI":"10.1093\/protein\/15.8.689","volume":"15","author":"K Oh","year":"2002","unstructured":"Oh K, Nam S and Kim HS (2002) Improvement of oxidative and thermostability of N-carbamyl-D-amino acid amidohydrolase by directed evolution. Protein Eng 15, 689\u2013695.","journal-title":"Protein Eng"},{"key":"3_CR27_3","doi-asserted-by":"publisher","first-page":"413","DOI":"10.1021\/bp0101942","volume":"18","author":"K Oh","year":"2002","unstructured":"Oh K, Nam S and Kim HS (2002) Directed evolution of N-carbamyl-D-amino acid amidohydrolase for simultaneous improvement of oxidative and thermal stability. Biotechnol Prog 18, 413\u2013417.","journal-title":"Biotechnol Prog"},{"key":"3_CR28_3","doi-asserted-by":"publisher","first-page":"317","DOI":"10.1038\/73773","volume":"18","author":"O May","year":"2000","unstructured":"May O, Nguyen PT and Arnold FH (2000) Inverting enantioselectivity by directed evolution of hydantoinase for improved production of L-methionine. Nature Biotechnol 18, 317\u2013320.","journal-title":"Nature Biotechnol"},{"key":"3_CR29_3","doi-asserted-by":"publisher","first-page":"211","DOI":"10.1002\/(SICI)1097-0290(20000420)68:2<211::AID-BIT10>3.0.CO;2-P","volume":"68","author":"GJ Kim","year":"2000","unstructured":"Kim GJ, Cheon YH and Kim HS (2000) Directed evolution of a novel N-carbamoylase\/D-hydantoinase fusion enzyme for functional expression with enhanced stability. Biotechnol Bioeng 68, 211\u2013217.","journal-title":"Biotechnol Bioeng"},{"key":"3_CR30_3","doi-asserted-by":"publisher","first-page":"179","DOI":"10.1016\/S0378-4347(99)00395-3","volume":"737","author":"M Pietzsch","year":"2000","unstructured":"Pietzsch M, Wiese A, Ragnitz K, et al. (2000) Purification of recombinant hydantoinase and L-N-carbamoylase from Arthrobacter aurescens expressed in Escherichia coli: comparison of wild-type and genetically modified proteins. J Chromatog B 737, 179\u2013186.","journal-title":"J Chromatog B"},{"key":"3_CR31_3","doi-asserted-by":"publisher","first-page":"7021","DOI":"10.1128\/JB.182.24.7021-7028.2000","volume":"182","author":"GJ Kim","year":"2000","unstructured":"Kim GJ, Lee DE and Kim HS (2000) Functional expression and characterization of the two cyclic amidohydrolase enzymes, allontoinase and a novel phenylhydantoinase, from Escherichia coli. J Bacteriol 182, 7021\u20137028.","journal-title":"J Bacteriol"},{"key":"3_CR32_3","doi-asserted-by":"publisher","first-page":"348","DOI":"10.1007\/s002530000385","volume":"54","author":"YP Chao","year":"2000","unstructured":"Chao YP, Chiang CJ, Lo TE and Fu H (2000a) Overproduction of D-hydantoinase and carbamoylase in a soluble form in Escherichia coli. Appl Microbiol Biotechnol 54, 348\u2013353.","journal-title":"Appl Microbiol Biotechnol"},{"key":"3_CR33_3","doi-asserted-by":"publisher","first-page":"680","DOI":"10.1007\/s002530100818","volume":"57","author":"M Hils","year":"2001","unstructured":"Hils M, Munch P, Altenbuchner J, et al. (2001) Cloning and characterization of genes from Agrobacterium sp. IP I-671 involved in hydantoin degradation. Appl Microbiol Biotechnol 57, 680\u2013688.","journal-title":"Appl Microbiol Biotechnol"},{"key":"3_CR34_3","doi-asserted-by":"publisher","first-page":"19","DOI":"10.1016\/S0168-1656(00)00398-9","volume":"86","author":"B Wilms","year":"2001","unstructured":"Wilms B, Wiese A, Syldatk C, et al. (2001) Development of an Escherichia coli whole cell biocatalyst for the production of L-amino acids. J Biotechnol 86, 19\u201330.","journal-title":"J Biotechnol"},{"key":"3_CR35_3","doi-asserted-by":"crossref","first-page":"2710","DOI":"10.1128\/AEM.64.7.2710-2715.1998","volume":"64","author":"J Dennis","year":"1998","unstructured":"Dennis J and Zylstra G (1998) Plasposons: Modular self-cloning minitransposon derivatives for rapid genetic analysis of gram-negative bacterial genomes. Appl Environ Microbiol 64, 2710\u20132715.","journal-title":"Appl Environ Microbiol"},{"key":"3_CR36_3","first-page":"386","volume":"235","author":"V DeLorenzo","year":"1994","unstructured":"DeLorenzo V and Timmis K (1994) Analysis and construction of stable phenotypes in gram-negative bacteria with Tn5- and Tn10-derived minitransposons in Methods in Enzymology, Eds. Clark V.L. and Bavoil P.M. Academic Press, San Diego 235, 386\u2013405.","journal-title":"San Diego"},{"key":"3_CR37_3","doi-asserted-by":"publisher","first-page":"391","DOI":"10.1007\/s00253-004-1597-3","volume":"65","author":"GF Matcher","year":"2004","unstructured":"Matcher GF, Burton SG and Dorrington RA (2004) Mutational analysis of the hydantoin hydrolysis pathway in Pseudomonas putida RU-KM3s. Appl Microbiol Biotechnol 65, 391\u2013400.","journal-title":"Appl Microbiol Biotechnol"},{"key":"3_CR38_3","doi-asserted-by":"publisher","first-page":"397","DOI":"10.1016\/S1381-1177(00)00036-9","volume":"11","author":"K Buchanan","year":"2001","unstructured":"Buchanan K, Burton SG, Dorrington RA, et al. (2001) A novel Pseudomonas putida strain with high levels of hydantoin-converting activity, producing L-amino acids. J Mol Catal B Enzym 11, 397\u2013406.","journal-title":"J Mol Catal B Enzym"},{"key":"3_CR39_3","doi-asserted-by":"publisher","first-page":"707","DOI":"10.1023\/A:1005351119657","volume":"20","author":"CJ Hartley","year":"1998","unstructured":"Hartley CJ, Kirchmann S, Burton SG and Dorrington RA (1998) Production of D-amino acids from D,L-5-substituted hydantoins by an Agrobacterium tumefaciens strain and isolation of a mutant with inducer independent expression of hydantoin hydrolysing activity. Biotechnol Lett 20, 707\u2013711.","journal-title":"Biotechnol Lett"},{"key":"3_CR40_3","volume-title":"Current protocols in molecular biology","author":"FM Ausubel","year":"1983","unstructured":"Ausubel FM, Brent R, Kingston RE, et al. (1983) Current protocols in molecular biology. Third edition. Wiley-Interscience, New York.","edition":"3"},{"key":"3_CR41_3","doi-asserted-by":"publisher","first-page":"1935","DOI":"10.1271\/bbb.57.1935","volume":"57","author":"Y Mukohara","year":"1993","unstructured":"Mukohara Y, Ishikawa T, Watabe K and Nakamura H (1993) Molecular cloning and sequencing of the gene for a thermostable N-carbamyl-L-amino acid amidohydrolase from Bacillus stearothermophilus strain NS1122A. Biosci Biotechol Biochem 57, 1935\u20131937.","journal-title":"Biosci Biotechol Biochem"},{"key":"3_CR42_3","doi-asserted-by":"publisher","first-page":"875","DOI":"10.1271\/bbb.62.875","volume":"62","author":"H Nanba","year":"1998","unstructured":"Nanba H, Ikenaka Y, Yamada Y, et al. (1998) Isolation of Agrobacterium sp. strain KNK712 that produces N-carbamyl-D-amino amidohydrolase, cloning of the gene for this enzyme, and properties of the enzyme. Biosci Biotechol Biochem 62, 875\u2013881.","journal-title":"Biosci Biotechol Biochem"},{"key":"3_CR43_3","doi-asserted-by":"publisher","first-page":"187","DOI":"10.1007\/s002030100309","volume":"176","author":"A Wiese","year":"2001","unstructured":"Wiese A, Syldatk C, Mattes R and Altenbuchner J (2001) Organization of genes responsible for the stereospecific conversion of hydantoins to \u03b1-amino acids in Arthrobacter aurescens DSM 3747. Arch Microbiol 176, 187\u2013196.","journal-title":"Arch Microbiol"},{"key":"3_CR44_3","doi-asserted-by":"publisher","first-page":"203","DOI":"10.1016\/j.enzmictec.2008.11.006","volume":"44","author":"M Jiwaji","year":"2009","unstructured":"Jiwaji M, Hartley CJ, Clark SA, et al. (2009) Enhanced hydantoin-hydrolyzing enzyme activity in an Agrobacterium tumefaciens strain with two distinct N-carbamoylases. Enzyme Microb Techol 44, 203\u2013209.","journal-title":"Enzyme Microb Techol"},{"key":"3_CR45_3","doi-asserted-by":"publisher","first-page":"43","DOI":"10.1007\/s002530100719","volume":"57","author":"CJ Hartley","year":"2001","unstructured":"Hartley CJ, Manford F, Burton SG and Dorrington RA (2001) Over-production of hydantoinase and N-carbamylamino acid amidohydrolase enzymes by regulatory mutants of Agrobacterium tumefaciens. Appl Microbiol Biotechnol 57, 43\u201349.","journal-title":"Appl Microbiol Biotechnol"},{"key":"3_CR46_3","doi-asserted-by":"publisher","first-page":"265","DOI":"10.1271\/bbb.58.265","volume":"58","author":"T Ishikawa","year":"1994","unstructured":"Ishikawa T, Mukohara Y, Watabe K. et al. (1994) Microbial conversion of DL-5-substituted hydantoins to the corresponding L-amino acids by Bacillus stearothermophilus NS1122A. Biosci Biotechol Biochem 58, 265\u2013270.","journal-title":"Biosci Biotechol Biochem"},{"key":"3_CR47_3","first-page":"152","volume":"255","author":"GJ Kim","year":"1997","unstructured":"Kim G.J, Park JH, Lee DC, et al. (1997) Primary structure, sequence analysis, and expression of the thermostable D-hydantoinase from Bacillus stearothermophilus SD-1. Mol Gen Genet 255, 152\u2013156.","journal-title":"Mol Gen Genet"},{"key":"3_CR48_3","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1128\/AEM.60.3.888-895.1994","volume":"60","author":"G LaPointe","year":"1994","unstructured":"LaPointe G, Viau S, Leblanc D, et al. (1994) Cloning, sequencing, and expression in Escherichia coli of the D-hydantoinase gene from Pseudomonas putida and distribution of homologous genes in other microorganisms. Appl Environ Microbiol 60, 888\u2013895.","journal-title":"Appl Environ Microbiol"},{"key":"3_CR49_3","first-page":"187","volume-title":"Molecular genetics of bacteria","author":"L Snyder","year":"2003","unstructured":"Snyder L and Champness W (2003) Molecular genetics of bacteria. 2nd edition, ASM Press, Washington, 187\u2013207.","edition":"2"}],"container-title":["Methods in Molecular Biology","Unnatural Amino Acids"],"original-title":[],"link":[{"URL":"http:\/\/link.springer.com\/content\/pdf\/10.1007\/978-1-61779-331-8_3.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,5,1]],"date-time":"2021-05-01T22:33:40Z","timestamp":1619908420000},"score":1,"resource":{"primary":{"URL":"http:\/\/link.springer.com\/10.1007\/978-1-61779-331-8_3"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2011,8,26]]},"ISBN":["9781617793301","9781617793318"],"references-count":49,"URL":"https:\/\/doi.org\/10.1007\/978-1-61779-331-8_3","relation":{},"ISSN":["1064-3745","1940-6029"],"issn-type":[{"value":"1064-3745","type":"print"},{"value":"1940-6029","type":"electronic"}],"subject":[],"published":{"date-parts":[[2011,8,26]]}}}