Phosphonopeptides as antibacterial agents: rationale, chemistry, and structure-activity relationships.

Antimicrobial Agents and Chemotherapy
F R AthertonP S Ringrose

Abstract

Peptide mimetics with C-terminal residues simulating natural amino acids have been designed as inhibitors of bacterial cell wall biosynthesis. The phosphonopeptide series consisting of various l and d residues of natural amino acids combined with 1-aminoalkyl (and aryl-alkyl-) phosphonic acid residues had the most interesting antibacterial properties when the C-terminal residue was l-1-aminoethylphosphonic acid. The in vitro antibacterial activities of representative phosphonodi- to phosphonohexapeptides were investigated. The antibacterial action of the active compounds has been explained in terms of transport into the bacterial cell and intracellular release of the alanine mimetic, which interferes with the biosynthesis of the peptidoglycan of the bacterial cell wall.

References

May 1, 1979·Antimicrobial Agents and Chemotherapy·J G AllenP S Ringrose
May 1, 1977·Proceedings of the National Academy of Sciences of the United States of America·L ChedidE Lederer
May 1, 1979·Antimicrobial Agents and Chemotherapy·F R AthertonP S Ringrose
Jan 1, 1975·Journal of Medicinal Chemistry·J W HuberL W Robertson
May 1, 1976·Journal of General Microbiology·M Kenig, E P Abraham
Nov 1, 1973·Journal of Bacteriology·W HammesO Kandler
May 10, 1974·Annals of the New York Academy of Sciences·H R Perkins, M Nieto
Apr 1, 1973·Journal of Bacteriology·G R Gale, A B Smith
Oct 1, 1965·Proceedings of the National Academy of Sciences of the United States of America·D J Tipper, J L Strominger
Nov 1, 1970·The Journal of Antibiotics·E L Dulaney
Sep 25, 1962·Biochemical and Biophysical Research Communications·S SHANKMANR SQUIRES

❮ Previous
Next ❯

Citations

Jan 1, 1996·Biopolymers·M Marraud, A Aubry
Jan 1, 1981·Pharmacology & Therapeutics·F C Neuhaus, W P Hammes
Jun 25, 2013·European Journal of Medicinal Chemistry·Asish K BhattacharyaSana Iram
Mar 8, 2003·Nuclear Medicine and Biology·C TsopelasF D L Bartholomeusz
Sep 15, 2011·Chemical Reviews·Paola ContiCarlo De Micheli
Sep 28, 2010·Chemical Communications : Chem Comm·Michael Kuemin, Wilfred A van der Donk
Jul 1, 1984·Proceedings of the National Academy of Sciences of the United States of America·W D KingsburyC Gilvarg
Mar 1, 1981·European Journal of Biochemistry·E Izbicka-DimitrijevićM Kochman
May 1, 1979·Antimicrobial Agents and Chemotherapy·J G AllenP S Ringrose
May 1, 1979·Antimicrobial Agents and Chemotherapy·F R AthertonP S Ringrose
Jun 1, 1980·Antimicrobial Agents and Chemotherapy·J G Allen, L J Lees
Oct 1, 1981·Antimicrobial Agents and Chemotherapy·F R AthertonD Westmacott
Oct 1, 1982·Antimicrobial Agents and Chemotherapy·F R AthertonD Westmacott
May 1, 1984·Antimicrobial Agents and Chemotherapy·P AngehrnD Westmacott
Feb 1, 1985·Antimicrobial Agents and Chemotherapy·H Osada, K Isono
Mar 1, 1988·Antimicrobial Agents and Chemotherapy·A A PatchettH G Bull
Jun 1, 1988·Antimicrobial Agents and Chemotherapy·W J LloydP Wong-Kai-In
Aug 1, 1988·Antimicrobial Agents and Chemotherapy·S MobasheryM Johnston
Nov 1, 2002·Journal of Clinical Microbiology·J D PerryA M Freydière
Jan 1, 1985·Current Medical Research and Opinion·A M EmmersonM J Hall
Dec 1, 1984·Journal of Pharmaceutical Sciences·V Nelson, P Mastalerz
Jan 3, 2009·Tetrahedron·Mario OrdóñezCarlos Cativiela
Sep 14, 2007·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Elif Ece Ilter, Zeynel Kiliç
Feb 13, 2008·FEMS Microbiology Reviews·Hélène BarreteauDidier Blanot
Jan 15, 2015·Chemical Communications : Chem Comm·Dorota Kowalczyk, Łukasz Albrecht
Apr 1, 1993·FEMS Microbiology Letters·E ZboińskaP Kafarski
Feb 28, 2002·Clinical Microbiology and Infection : the Official Publication of the European Society of Clinical Microbiology and Infectious Diseases·J.M.T. Hamilton-Miller
Mar 30, 2017·Organic & Biomolecular Chemistry·K PallitschF Hammerschmidt
Jan 12, 2019·Organic & Biomolecular Chemistry·M Mercedes Jiménez-AndreuCarlos Cativiela
Mar 27, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Emma C L MarrsJohn D Perry
Jan 1, 1992·Critical Reviews in Biotechnology·H H GadebuschS B Zimmerman
Mar 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Laszlo A KondacsMark Gray
Jun 15, 1990·FEMS Microbiology Letters·E ZboińskaP Kafarski
Feb 9, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Raquel P Herrera
Apr 2, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Keng Tiong NgMark Gray
Jul 23, 2008·Journal of the American Chemical Society·Joshua P Abell, Hisashi Yamamoto
Oct 1, 1983·Antimicrobial Agents and Chemotherapy·F R AthertonD Westmacott

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