The Synthesis and in vitro Study of 9-fluorenylmethoxycarbonyl Protected Non-Protein Amino Acids Antimicrobial Activity

Authors

  • T.H. Sargsyan Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan, 0056, Yerevan, Armenia; Yerevan State University, Institute of Pharmacy, 1 A. Manoogian str., 0025 Yerevan, Armenia
  • L.A. Stepanyan Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan, 0056, Yerevan, Armenia
  • M.H. Israyelyan Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan, 0056, Yerevan, Armenia
  • H.I. Hakobyan Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan, 0056, Yerevan, Armenia
  • S.M. Jamgaryan Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan, 0056, Yerevan, Armenia
  • A.A. Gasparyan Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan, 0056, Yerevan, Armenia
  • A.S. Saghyan Scientific and Production Center “Armbiotechnology” NAS RA, 14 Gyurjyan, 0056, Yerevan, Armenia; Yerevan State University, Institute of Pharmacy, 1 A. Manoogian str., 0025 Yerevan, Armenia

DOI:

https://doi.org/10.18321/ectj1546

Keywords:

protecting group , peptide synthesis , non-protein amino acid , antimicrobial activity

Abstract

Using the 9-fluorenylmethoxycarbonyl protecting group, 9-fluorenylme­thoxycarbonyl-(S)-β-(N-imidazolyl)-α-alanine protected non-protein amino acid, not described in the literature, were developed. Then 9-fluorenyl­methoxycarbonyl-(S)-α-methylphenylalanine, 9-fluorenylmethoxycarbon­yl-(S)-α-allylglycine, 9-fluorenylmethoxycarbonyl-(S)-α-propargylglycine were synthesized by the same method. It was shown, that the 9-fluorenyl­methoxycarbonyl-(S)-β-(N-imidazolyl)-α-alanine (3) inhibited the growth of Gram-negative Salmonella tуphimurium G-38 and 9-fluorenyl-methoxycar­bonyl-(S)-α-methyl-phenylalanine (4) inhibited the growth Gram-positive Bacillus subtilis 17-89 bacteria.

References

(1). P. Vlieghe, V. Lisowski, J. Martinez, M. Khrestchatisky, Drug Discov. Today 15 (2010) 40–56. Crossref

(2). K. Fosgerau, T. Hoffmann, Drug Discov. Today 20 (2015) 122–128. Crossref

(3). L.L. Jolene, M.K Dunn, Bioorg. Med. Chem. 26 (2018) 2700–2707. Crossref

(4). A. Hughes, Amino Acids, Peptides and Proteins in organic Chemistry. Protection Reactions, Medicinal Chemistry & Combinatoral Synthesys. Wiley-VCH Verlag GmbH & Co. KGaA Weinhei, 2011, p. 538. Crossref

(5). K. Tao, A. Levin, L. Adler-Abramovich, E. Gazit, Chem. Soc. Rev. 45 (2016) 3935–3953. Crossref

(6). W. Li, X. Hu, J. Chen, Z. Wei, C. Song, R. Huang, J. Mater. Sci. Mater. Med. 31 (2020) 73. Crossref

(7). J. Gonzalez, J. Ramirez, J.P. Schwans, Amino Acids. 48 (2016) 2755–2763. Crossref

(8). E.C. Parente, M. Brienza, M. Moles, A. Ricciardi, J. Microbiol. Methods. 22 (1996) 95–108. Crossref

(9). A.W. Bauer, M.M. Kirby, J.C. Sherris, M. Turk, Am. J. Clin. Pathol. 45 (1996) 493–496. Crossref

(10). (10). EUCAST Disk Diffusion Method for Antimicrobial Susceptibility Testing, Version 9.0 (January 2021), URL

(11). O. Bellotto, S. Semeraro, A. Bandiera, F. Tramer, N. Pavan, S. Marchesan, Pharmaceutics 14 (2022) 446–465. Crossref

(12). G. Wang, X. Li, Z. Wang, Nucleic Acids Res. 44 (2016) D1087–D1093. Crossref

(13). N. Kerru, L. Gummidi, S. Maddila, K.K. Gangu, B. Sreekantha, A. Jonnalagadda, Molecules 25 (2020) 1909–1951. Crossref

(14). A. Kumar, A.K. Singh, H. Singh, V. Vijayan, D. Kumar, J. Naik, et al., Pharmaceuticals 16 (2023) 299–367. Crossref

Downloads

Published

2024-02-15

How to Cite

Sargsyan, T., Stepanyan, L., Israyelyan, M., Hakobyan, H., Jamgaryan, S., Gasparyan, A., & Saghyan, A. (2024). The Synthesis and in vitro Study of 9-fluorenylmethoxycarbonyl Protected Non-Protein Amino Acids Antimicrobial Activity . Eurasian Chemico-Technological Journal, 25(4), 235–240. https://doi.org/10.18321/ectj1546

Issue

Section

Articles