Synthetic Methods of Phosphonopeptides

Phosphonopeptides are phosphorus analogues of peptides and have been widely applied as enzyme inhibitors and antigens to induce catalytic antibodies. Phosphonopeptides generally contain one aminoalkylphosphonic acid residue and include phosphonopeptides with C-terminal aminoalkylphosphonic acids and...

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Published in:Molecules (Basel, Switzerland) Switzerland), 2020-12, Vol.25 (24), p.5894
Main Author: Xu, Jiaxi
Format: Article
Language:English
Subjects:
Acids
Aldehydes
Amides
Antigens
Chemistry Techniques, Synthetic
Chloride
Chlorides - chemistry
Enzyme inhibitors
Enzymes
Esters
Halogenation
Methods
Organophosphorus Compounds - chemistry
Oxalates - chemistry
Oxidation
peptide
Peptides
Peptides - chemical synthesis
Peptides - chemistry
phosphonamidate
phosphonopeptide
Phosphoproteins - chemical synthesis
Phosphoproteins - chemistry
Phosphorus
Reagents
Review
β-phosphonopeptide
γ-phosphonopeptide
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description Phosphonopeptides are phosphorus analogues of peptides and have been widely applied as enzyme inhibitors and antigens to induce catalytic antibodies. Phosphonopeptides generally contain one aminoalkylphosphonic acid residue and include phosphonopeptides with C-terminal aminoalkylphosphonic acids and phosphonopeptides with a phosphonamidate bond. The phosphonamidate bond in the phosphonopeptides is generally formed via phosphonylation with phosphonochloridates, condensation with coupling reagents and enzymes, and phosphinylation followed by oxidation. Pseudo four-component condensation reaction of amides, aldehydes, alkyl dichlorophosphites, and amino/peptide esters is an alternative, convergent, and efficient strategy for synthesis of phosphonopeptides through simultaneous construction of aminoalkylphosphonic acids and formation of the phosphonamidate bond. This review focuses on the synthetic methods of phosphonopeptides containing a phosphonamidate bond.
doi_str_mv 10.3390/molecules25245894
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source Publicly Available Content Database (Proquest) (PQ_SDU_P3); PubMed Central
subjects Acids
Aldehydes
Amides
Antigens
Chemistry Techniques, Synthetic
Chloride
Chlorides - chemistry
Enzyme inhibitors
Enzymes
Esters
Halogenation
Methods
Organophosphorus Compounds - chemistry
Oxalates - chemistry
Oxidation
peptide
Peptides
Peptides - chemical synthesis
Peptides - chemistry
phosphonamidate
phosphonopeptide
Phosphoproteins - chemical synthesis
Phosphoproteins - chemistry
Phosphorus
Reagents
Review
β-phosphonopeptide
γ-phosphonopeptide
title Synthetic Methods of Phosphonopeptides
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