Abstract
We studied the antimicrobial properties of 32 new non-protein compounds synthetized in the Scientific and Production Center “Armbiotechnology” by the method of asymmetric synthesis; new analogs of L-histidine and L-isoleucine were found. Via chemical mutagenesis, we obtained new mutants of the wild strain of Brevibacterium flavum 14067 resistant to (S)-β-[4-phenyl-3-(3’-hydroxypropyl)-5-thioxo-1,2,4-thiazole-1-yl]-α-alanine (an analog of histidine) and to (2S,3R)-oxyleucine (an analog of isoleucine). It was found that the synthesis rate of histidine and isoleucine in some mutants is higher than that of most active strain-producers resistant to one of these amino acids analogs described in literature. Our data prove the efficacy of the use of new analogs as selective agents for the screening of highly active strains producing histidine and isoleucine.
Similar content being viewed by others
References
Saghyan, A.S., Enantiomerno chistye nebelkovye aminokisloty: sposoby polucheniya (Enantiomerically Pure Non-Protein Amino Acids: Methods of Obtaining), Moscow: Nauka, 2010.
Janecka, A., Janecki, T., Bowers, C., and Folkers, K., J. Med. Chem., 1995, vol. 38, no. 15, pp. 2922–2924.
Nagren, K. and Halldin, C., J. Label. Compounds Radiopharm., 1998, vol. 41, no. 9, pp. 831–841.
Chitchyan, M., Melkumyan, M., Avetisyan, N., Oganezova, G., Oganesyan, N., Hambardzumyan, A., and Oganesyan, N., Biol. Zh. Arm., 2007, vol. 59, no. 3-4, pp. 248–253.
Barrett, G.C., Chemistry and Biochemistry of the Amino Acids, London: Chapmanand Hall, 1985.
Ikeda, Y., Kawahara, S., Taki, M., Kuno, A., Hasegawa, T., and Taira, K., Protein Engin., 2003, vol. 16, no. 9, pp. 699–706.
Stanchev, M., Pajpanova, T., and Golovinsky, F., Amino Acids, 2000, vol. 18, no. 2, pp. 77–91.
Davtyan, A., Arstamyan, L., Keleshyan, S., Karapetyan, Zh., Avetisova, G., and Chakhalyan, A., in Screening of Non-protein Amino Acids for Selection of Natural Amino Acids Analogs. Book of Abstracts of Intern. Sci. Sem., Yerevan, Armenia, 2012, p. 70.
Schlegel, H.G., General Microbiology, 6th ed., Cambridge: Cambridge Univ. Press, 1986.
Ikeda, M., Adv. Biochem. Eng./Biotechnol., 2003, vol. 79, pp. 1–35.
Kramer, R., Food Biotechnol., 2004, vol. 18, no. 2, pp. 7–46.
Leuchtenberger, W., Huthmacher, K., and Drauz, K., Appl. Microbiol. Biotechnol., 2005, vol. 69, no. 1, pp. 1–8.
Demain, A.L., Industr. Biotechnol., 2007, vol. 3, no. 3, pp. 269–283.
Henning, V. and Stefan, B., Org. Biomol. Chem., 2007, vol. 5, no. 3, pp. 406–430.
Kim, S.M. and Yang, J.W., Org. Biomol. Chem., 2013, vol. 11, no. 29, pp. 4737–4749.
Saghyan, A., Mkrtchyan, G., Dadayan, A., Petrosyan, S., Geolchanyan, A., Simonyan, H., Mkrtchyan, A., Mkrtchyan, S., Gevorgyan, A., Iaroshenko, V., and Langer, P., Tetrahedron: Asymmetry, 2013, vol. 24, no. 4, pp. 229–232.
Priyanka, S., Krishnananda, S., Sanjit, K., and Gautam, P., Or. Biomol. Chem., 2014, vol. 12, no. 33, pp. 6297–6339.
Saghyan, A.S., Geolchanyan, A.V., Avetisova, G.E., Tajiryan, H.Kh., and Makarova, L.L., in Catalog of Scientific Research Institute of Biotechnology. Yerevan, 2008.
Chakhalyan, A., Keleshyan, S., Karapetyan, Zh., Davtyan, A., Koloyan, A., and Avetisova, G., Biol. Zh. Arm., 2008, vol. 60, no. 1-2, pp. 103–108.
Miller, J., Experiments in Molecular Genetics, New York: Cold Spring Harbor, 1972.
Zhdanova, N.I. and Gusyatiner, M.M., Metody selektsii i svoistva shtammov mikroorganizmov-produtsentov aminokislot. Obzor (Selection Methods and Properties of Strains of Microorganisms Producing Amino Acids: Overview), Moscow: VNIISENTI, 1985.
Chakhalyan, A., Keleshyan, S., Karapetyan, Zh., Davtyan, A., Avetisova, G., and Saghyan, A., Biotekhnologiya, 2009, no. 3, pp. 24–28.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.Kh. Chakhalyan, S.Gh. Keleshyan, Zh.V. Karapetyan, A.G. Davtyan, G.Y. Avetisova, L.H. Melkonyan, A.S. Dadayan, A.S. Saghyan, 2016, published in Prikladnaya Biokhimiya i Mikrobiologiya, 2016, Vol. 52, No. 1, pp. 62–67.
Rights and permissions
About this article
Cite this article
Chakhalyan, A.K., Keleshyan, S.G., Karapetyan, Z.V. et al. The inhibitory properties of new non-protein amino acids and the screening of effective analogs of L-amino acids for the selection of highly active strain-producers. Appl Biochem Microbiol 52, 51–55 (2016). https://doi.org/10.1134/S0003683816010038
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0003683816010038