225
Views
0
CrossRef citations to date
0
Altmetric
Original Articles

Biocatalytic Synthesis of γ-glutamyl-L-leucine, a Kokumi-Imparting Dipeptide, by Bacillus licheniformis γ-Glutamyltranspeptidase

, , , , &

References

  • Aginsky, V.N. (1994). A new version of the internal standard method in quantitative thin layer chromatography. J. Planar Chromatogr. 7: 309–314.
  • Allison, R.D. (1985). γ-Glutamyl trnaspeptidase: kinetics and mechanism. Methods Enzymol. 113:419–437.
  • Bryan, J. (2008). Psychological effects of dietary components of tea: caffeine and L-theanine. Nutr. Rev. 66: 82–90.
  • Castellano, I., Merlino, A. (2012). γ-Glutamyl transpeptidases: sequence, structure, biochemical properties, and biotechnological applications. Cell. Mol. Life Sci. 69: 3381–3394.
  • Castonguay, R., Lherbet, C., Keiller, J.W. (2003). Kinetic studies of a rat kidney γ-glutamyltranspeptidase deacylation reveal a general base-catalyzed mechanism. Biochemistry. 42: 11504–11513.
  • Chen, X., Su, L., Wu, D., Wu, J. (2014). Application of recombinant Bacillus subtilis γ-glutamyltranspeptidase to the production of L-theanine. Process Biochem. 49: 1429–1439.
  • Chen, Y.Y., Lo, H.F., Wang, T.F., Lin, M.G., Lin, L.L., Chi, M.C. (2015). Enzymatic synthesis of γ-L-glutamyl-S-allyl-L-cysteine, a naturally occurring organosulfur compound from garlic, by Bacillus licheniformis γ-glutamyltranspeptidase. Enzyme Microb. Technol. 75-76: 18–24.
  • Dunkel, A., Koester, J., Hofmann, T. (2007). Molecular and sensory characterization of γ-glutamyl peptides as key contributors to the kokumi taste of edible beans (Phaseolus vulgaris L.). J. Agric. Food Chem. 55: 6712–6719.
  • Han, L., Hiratake, J., Kamiyama, A., Sakata, K. (2007). Design, synthesis, and evaluation of γ-phosphono diester analogues of glutamate as highly potent inhibitors and active site probes of γ-glutamyltranspeptidase. Biochemistry. 46: 1432–1447.
  • Kuroda, M., Yamanaka, T., Miyamura, N. (2004). Change in taste and flavor of food during the aging with heating process: generation of “kokumi” flavor during the heating of beef soup and beef extract. Jpn. J. Taste Smell Res. 11: 175–180.
  • Lherbet, C., Keiller, J.W. (2004). Probing the stereochemistry of the active site of γ-glutamyl transpeptidase using sulfur derviatives of L-glutamic acid. Org. Biomol. Chem. 2: 238–245.
  • Lin, L.L., Chen, Y.Y., Chi, M.C., Merlino, A. (2014). Low resolution X-ray structure of γ-glutamyltranspeptidase from Bacillus licheniformis: opened active site cleft and a cluster of acid residues potentially involved in the recognition of a metal ion. Biochim. Biophys. Acta. 1844: 1523–1529.
  • Lin, L.L., Chou, P.R., Hua, Y.W., Hsu, W.H. (2006). Overexpression, one-step purification, and biochemical characterization of a recombinant γ-glutamyltranspeptidase from Bacillus licheniformis. Appl. Microbiol. Biotechnol. 73: 103–112.
  • Lin, L.L., Yang, L.Y., Hu, H.Y., Lo, H.F. (2008). Influence of N-terminal truncations on the functional expression of Bacillus licheniformis γ-glutamyltranspeptidase in recombinant. Escherichia coli. Curr. Microbiol. 57: 603–608.
  • Lin, M.G., Chi, M.C., Chen, Y.Y., Wang, T.F., Lo, H.F. (2016). Site-directed mutagenesis of a conserved Asn450 residue of Bacillus licheniformis γ-glutamyltranspeptidase. Int. J. Biol. Macromol.. 91: 416–425.
  • Minami, H., Suzuki, H., Kumagai, H. (2003). Salt-tolerant γ-glutamyltranspeptidase from Bacillus subtilis 168 with glutaminase activity. Enzyme Microb. Technol. 23: 431–438.
  • Morelli, C.F., Calvio, C., Biagiotti, M., Speranza, G. (2014). pH-Dependent hydrolase, glutaminase, transpeptidase and autotranspeptidase activities of Bacillus subtilis γ-glutamyltranspeptidase. Febs J. 281: 232–245.
  • Ohsu, T., Amino, Y., Nagasaki, H., Yamanaka, S., Hatanaka, T., Maruyama, Y., Miyamura, N., Eto, Y. (2010). Involvement of the calcium-sensing receptor in human taste perception. J. Biol. Chem. 285: 1016–1022.
  • Shuai, Y., Zhang, T., Jiang, B., Mu, W. (2010). Development of efficient enzymatic production of theanine by γ-glutamyltranspeptidase from a newly isolated strain of Bacillus subtilis SK11.004. J. Sci. Food Agric. 90: 2563–2567.
  • Speranza, G., Morelli, C.F. (2012). γ-Glutamyl transpeptidase-catalyzed synthesis of naturally flavor enhancers. J. Mol. Catal. B Enzym. 84: 65–71.
  • Suzuki, H., Izuka, S., Minami, H., Miyakawa, H. (2003). Use of bacterial γ-glutamyltranspeptidase for enzymatic synthesis of γ-D-glutamyl compounds. Appl. Environ. Microbiol. 69: 6399–6404.
  • Suzuki, H., Kumagai, H. (2002). Autocatalytic processing of γ-glutamyltranspeptidase. J. Biol. Chem. 277: 43536–43543.
  • Suzuki, H., Kumagai, H., Tochikura, T. (1986). γ-Glutamyltranspeptidase from Escherichia coli K-12: purification and properties. J. Bacteriol. 168: 1325–1331.
  • Suzuki, H., Yamada, C., Kato, K. (2007). γ-Glutamyl compounds and their enzymatic production using bacterial γ-glutamyltranspeptidase. Amino Acids. 32: 333–340.
  • Tate, S.S. (1986). Single-chain precursor of renal γ-glutamyl transpeptidase. FEBS Lett. 194: 33–38.
  • Tate, S.S., Meister, A. (1974). Interaction of γ-glutamyl transpeptidase with amino acids, dipeptides, and derivatives and analogs of glutathione. J. Biol. Chem. 249: 7593–7602.
  • Thompson, G.A., Meister, A. (1976). Hydrolysis and transfer reactions catalyzed by γ-glutamyl transpeptidase: evidence for separate substrate sites and the high affinity of L-cysteine. Biochem. Biophys. Res. Commun. 71: 32–36.
  • Toelstede, S., Dunkel, A., Hofmann, T. (2009). A series of kokumi peptides impart the long-lasting mouthfulness of matured Gouda cheese. J. Agric. Food Chem. 57: 1440–1448.
  • Ueda, Y., Sakaguchi, M., Hirayama, K., Miyajima, R., Kimizuka, A. (1990). Characteristic flavor constituents in water extract of garlic. Agric. Biol. Chem. 54: 163–169.
  • Ueda, Y., Tsubuku, T., Miyajima, R. (1994). Composition of sulfur-containing components in onion and their flavor characters. Biosci. Biotechnol. Biochem. 61: 108–110.
  • Yang, J.C., Liang, W.C., Chen, Y.Y., Chi, M.C., Lo, H.F., Chen, H.L., Lin, L.L. (2011). Biophysical characterization of Bacillus licheniformis and Escherichia coli γ-glutamyltranspeptidases: a comparative analysis. Int. J. Biol. Macromol. 48: 414–422.
  • Zhang, H.J., Zhang, W.G., Wang, Z.Y., Zhan, Y.P., Xu, L.S., Liu, J.Z., Liu, Q., Jiao, Q.C. (2013). Enzymatic synthesis of theanine with Escherichia coli γ-glutamyltranspeptidase from a series of γ-glutamyl anilide substrate analogues. Biotechnol. Bioprocess Eng. 18: 358–364.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.