Synthesis and biological activity of dehydrophos derivatives

被引:0
作者
Jiménez-Andreu M.M. [1 ]
Lucía Quintana A. [2 ,3 ]
Aínsa J.A. [2 ,3 ]
Sayago F.J. [1 ]
Cativiela C. [1 ]
机构
[1] Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea ISQCH, CSIC-Universidad de Zaragoza, Zaragoza
[2] Departamento de Microbiología, Medicina Preventiva y Salud Pública, Facultad de Medicina, BIFI, Universidad de Zaragoza, Zaragoza
[3] CIBER Enfermedades Respiratorias, Instituto de Salud Carlos III, Madrid
关键词
D O I
10.1039/c8ob03079k
中图分类号
学科分类号
摘要
The synthesis of dehydrophos derivatives featuring modified peptide chains, characterized by the presence of substituents in the vinyl moiety, or possessing a phosphonic acid monoalkyl ester other than the monomethyl ester one, has been accomplished by a versatile procedure based on Horner-Wadsworth-Emmons olefination with suitable aldehydes and on the selective hydrolysis of the dialkyl phosphonate group. Such derivatives have been tested against a series of bacterial strains, using the naturally occurring peptide, dehydrophos, for comparison. Thus, the effects of the aforementioned structural variations on antimicrobial activity have been studied. ©2019 The Royal Society of Chemistry.
引用
收藏
页码:1097 / 1112
页数:15
相关论文
共 54 条
  • [1] Hunt A.H., Elzey T.K., J. Antibiot., 41, (1988)
  • [2] Johnson R.D., Kastner R.M., Larsen S.H., Ose E.E., Antibiotic A53868 and process for production thereof, US, (1984)
  • [3] Johnson R.D., Kastner R.M., Larsen S.H., Ose E.E., Process for production antibiotic A53868, US, (1984)
  • [4] Whitteck J.T., Ni W., Griffin B.M., Eliot A.C., Thomas P.M., Kelleher N.L., Metcalf W.W., Van Der Donk W.A., Angew. Chem., Int. Ed., 46, pp. 9089-9092, (2007)
  • [5] Ulrich E.C., Bougioukou D.J., Van Der Donk W.A., ACS Chem. Biol., 13, pp. 537-541, (2018)
  • [6] Peck S.C., Van Der Donk W.A., Curr. Opin. Chem. Biol., 17, pp. 580-588, (2013)
  • [7] Bougioukou D.J., Mukherjee S., Van Der Donk W.A., Proc. Natl. Acad. Sci. U. S. A., 110, pp. 10952-10957, (2013)
  • [8] Nair S.K., Van Der Donk W.A., Arch. Biochem. Biophys., 505, pp. 13-21, (2011)
  • [9] Circello B.T., Eliot A.C., Lee J.H., Van Der Donk W.A., Metcalf W.W., Chem. Biol., 17, pp. 402-411, (2010)
  • [10] Lee J.H., Bae B., Kuemin M., Circello B.T., Metcalf W.W., Nair S.K., Van Der Donk W.A., Proc. Natl. Acad. Sci. U. S. A., 107, pp. 17557-17562, (2010)