Phosphonopeptides containing free phosphonic groups: recent advances
Author:
Open Access
- 9 July 2020
- journal article
- review article
- Published by Royal Society of Chemistry (RSC) in RSC Advances
- Vol. 10 (43) , 25898-25910
Abstract
Phosphonopeptides are mimetics of peptides in which phosphonic acid or related (phosphinic, phosphonous etc.) group replaces either carboxylic acid group present at C-terminus, is located in the peptidyl side chain, or phosphonamidate or phosphinic acid mimics peptide bond. Acting as inhibitors of key enzymes related to variable pathological states they display interesting and useful physiologic activities with potential applications in medicine and agriculture. Since the synthesis and biological properties of peptides containing C-terminal diaryl phosphonates and those with phosphonic fragment replacing peptide bond were comprehensively reviewed, this review concentrate on peptides holding free, unsubstituted phosphonic acid moiety. There are two groups of such mimetics: (i) peptides in which aminophosphonic acid is located at C-terminus of the peptide chain with most of them (including antibiotics isolated from bacteria and fungi) exhibiting antimicrobial activity; (ii) non-hydrolysable analogues of phosphonoamino acids, which are useful tools to study physiologic effects of phosphorylations.Keywords
Funding Information
- Narodowe Centrum Nauki (2016/21/B/ST5/00115)
This publication has 95 references indexed in Scilit:
- Synthesis and Modifications of Phosphinic Dipeptide AnaloguesMolecules, 2012
- Synthesis of a Phosphoserine Mimetic Prodrug with Potent 14-3-3 Protein Inhibitory ActivityChemistry & Biology, 2012
- Peptoid–Peptide Hybrid Ligands Targeting the Polo Box Domain of Polo‐Like Kinase 1ChemBioChem, 2012
- Reaction of diethyl 1-acylamino-2,2-dichloroethenylphosphonates with amino acids estersRussian Journal of General Chemistry, 2012
- Identification of High Affinity Polo-like Kinase 1 (Plk1) Polo-box Domain Binding Peptides Using Oxime-Based DiversificationACS Chemical Biology, 2012
- Facile synthesis of hybrid sulfonophosphinodipeptides composing of taurines and 1-aminoalkylphosphinic acidsAmino Acids, 2011
- The Antibiotic Dehydrophos Is Converted to a Toxic Pyruvate Analog by Peptide Bond Cleavage in Salmonella entericaAntimicrobial Agents and Chemotherapy, 2011
- Development of Stable Phosphohistidine AnaloguesJournal of the American Chemical Society, 2010
- Structural basis for the inhibition of the essential Plasmodium falciparum M1 neutral aminopeptidaseProceedings of the National Academy of Sciences, 2009
- Stoffwechselprodukte von Mikroorganismen. 98. Mitteilung. Phosphinothricin und Phosphinothricyl‐Alanyl‐AlaninHelvetica Chimica Acta, 1972