Synthesis of N-carbobenzoxy-l-aspartyl-l-phenylalanine methyl ester catalyzed by thermolysin variants with improved activity

Endo, 1962, Studies on protease produced by thermophilic bacteria, J Ferment Technol, 40, 346 van den Burg, 2004, Thermolysin, vol. 1, 374 Inouye, 2003, Thermolysin, 1019 Latt, 1969, Thermolysin: a zinc metalloenzyme, Biochem Biophys Res Commun, 37, 333, 10.1016/0006-291X(69)90739-6 Feder, 1971, Studies on the role of calcium in thermolysin, Biochemistry, 10, 4552, 10.1021/bi00800a032 Tajima, 1976, Role of calcium ions in the thermostability of thermolysin and Bacillus subtilis var. amylosacchariticus neutral protease, Eur J Biochem, 64, 243, 10.1111/j.1432-1033.1976.tb10293.x Morihara, 1970, Thermolysin: kinetic study with oligopeptides, Eur J Biochem, 15, 374, 10.1111/j.1432-1033.1970.tb01018.x Inouye, 1996, Effect of amino acid residues at the cleavable site of substrates on the remarkable activation of thermolysin by salts, Biochem J, 315, 133, 10.1042/bj3150133 Titani, 1972, Amino-acid sequence of thermolysin, Nature, 238, 35 Holmes, 1982, Structure of thermolysin refined at 1.6Å resolution, J Mol Biol, 160, 623, 10.1016/0022-2836(82)90319-9 Hangauer, 1984, An interactive computer graphics study of thermolysin-catalyzed peptide cleavage and inhibition by N-carboxymethyl dipeptides, Biochemistry, 23, 5730, 10.1021/bi00319a011 Mock, 1994, Binding to thermolysin of phenolate-containing inhibitors necessitates a revised mechanism of catalysis, Biochem J, 302, 57, 10.1042/bj3020057 Inouye, 1992, Effects of salts on thermolysin: activation of hydrolysis and synthesis of N-carbobenzoxy-l-aspartyl-l-phenylalanine methyl ester, and a unique change in the absorption spectrum of thermolysin, J Biochem, 112, 335, 10.1093/oxfordjournals.jbchem.a123901 Isowa, 1979, The thermolysin-catalyzed condensation reactions of N-substituted aspartic and glutamic acids with phenylalanine alkyl esters, Tetrahedron Lett, 20, 2611, 10.1016/S0040-4039(01)86363-2 Oyama, 1981, On the mechanism of the action of thermolysin: kinetic study of the thermolysin-catalysed condensation reaction of N-benzyloxycarbonyl-l-aspartic acid with l-phenylalanine methyl ester, J Chem Soc Perkin II, 356, 10.1039/p29810000356 Nakanishi, 1986, Kinetics and equilibrium of enzymatic synthesis of peptides in aqueous/organic biphasic systems, thermolysin-catalyzed synthesis of N-(benzyloxycarbonyl)-l-aspartyl-l-phenylalanine methyl ester, Eur J Biochem, 161, 541, 10.1111/j.1432-1033.1986.tb10476.x Miyanaga, 2000, Kinetics and equilibrium for thermolysin-catalyzed syntheses of dipeptide precursors in aqueous/organic biphasic systems, J Biosci Bioeng, 90, 43, 10.1016/S1389-1723(00)80032-8 Inouye, 1998, Sodium chloride enhances markedly the thermal stability of thermolysin as well as its catalytic activity, Biochim Biophys Acta, 1388, 209, 10.1016/S0167-4838(98)00189-7 Inouye, 1997, Effects of pH, temperature, and alcohols on remarkable activation of thermolysin by salts, J Biochem, 122, 358, 10.1093/oxfordjournals.jbchem.a021761 Oneda, 2004, Substrate-dependent activation of thermolysin by salt, Biosci Biotechnol Biochem, 68, 1811, 10.1271/bbb.68.1811 Inouye, 1998, Effect of salts on the solubility of thermolysin: a remarkable increase in the solubility as well as the activity by the addition of salts without aggregation or dispersion of thermolysin, J Biochem, 123, 847, 10.1093/oxfordjournals.jbchem.a022014 Hanzawa, 1999, Thermolysin, 2527 Yasukawa, 2007, Improving the activity and stability of thermolysin by site-directed mutagenesis, Biochim Biophys Acta, 1774, 1281, 10.1016/j.bbapap.2007.08.002 Matsumiya, 2004, Analysis of autodegradation sites of thermolysin and enhancement of its thermostability by modifying Leu155 at an autodegradation site, J Biochem, 135, 547, 10.1093/jb/mvh067 Matsumiya, 2005, Mutational effect for stability in a conserved region of thermolysin, Lett Appl Microbiol, 40, 329, 10.1111/j.1472-765X.2005.01677.x Takita, 2008, Effects of introducing negative charges into the molecular surface of thermolysin by site-directed mutagenesis on its activity and stability, Biochim Biophys Acta, 1784, 481, 10.1016/j.bbapap.2007.12.004 Kusano, 2006, Engineering of the pH-dependence of thermolysin activity as examined by site-directed mutagenesis of Asn112 located at the active site of thermolysin, J Biochem, 139, 1017, 10.1093/jb/mvj112 Tatsumi, 2007, Effects of site-directed mutagenesis of the surface residues Gln128 and Gln225 of thermolysin on its catalytic activity, J Biochem, 141, 835, 10.1093/jb/mvm087 Kusano, 2009, Insights into the catalytic roles the polypeptide regions in the active site of thermolysin and generation of the thermolysin variants with high activity and stability, J Biochem, 145, 103, 10.1093/jb/mvn140 Feder, 1968, A spectrophotometric assay for neutral protease, Biochem Biophys Res Commun, 32, 326, 10.1016/0006-291X(68)90389-6 Salam, 2008, Protease-catalyzed dipeptide synthesis from N-protected amino acid carbamoylmethyl ester and free amino acids in frozen aqueous solutions, Enzyme Microb Technol, 43, 537, 10.1016/j.enzmictec.2008.09.003 Yasukawa, 2007, A new method for the extracellular production of recombinant thermolysin by co-expressing the mature sequence and pro-sequence in Escherichia coli, Protein Eng Des Sel, 20, 375, 10.1093/protein/gzm031 Sakoda, 1976, Determination of the best-fit values of kinetic parameters of the Michaelis–Menten equation by the method of least squares with Taylor expansion, J Biochem, 80, 547, 10.1093/oxfordjournals.jbchem.a131310 Trusek-Holownia, 2003, Synthesis of ZAlaPheOMe, the precursor of bitter dipetide in the two-phase ethyl acetate–water system catalyzed by thermolysin, J Biotechnol, 102, 153, 10.1016/S0168-1656(03)00024-5 Murakami, 2000, Continuous enzymatic production of peptide precursor in aqueous/organic biphasic medium, Biotechnol Bioeng, 69, 57, 10.1002/(SICI)1097-0290(20000705)69:1<57::AID-BIT7>3.0.CO;2-J