Abstract
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.
Highlights
This review focuses on the synthetic methods of phosphonopeptides, including α, β, γ, and δ-phosphonopeptides (Figure 1), with a phosphonamidate bond, especially focuses on the synthetic strategies for the formation of the phosphonamidate bond, excluding the modification of phosphonopeptides
N-phthalylaminome triisopropyl and further treated pentachloride to give the corresponding phthalyl(Phth)aminomethylphosphonate was prepared from phthalylaminomethyl chloride and thylphosphonochloridate, which reacted with ethyl glycinate in the presence of triethylamine to isopropyl N-phthalylaminomethylphosphonochloridate, which reacted with ethyl in the triisopropyl phosphite and further treated with phosphorus pentachloride to give theglycinate corresponding give rise to protected phosphonopeptide
Subsequent reaction with amino and peptide esters generated the phosphonopeptides in good yields
Summary
They generally contain one aminoalkylphosphonic acid residue and include phosphonopeptides with C-terminal aminoalkylphosphonic acids and phosphonopeptides containing a phosphonamidate bond [1,2]. Phosphonopeptides have been used as antibacterial agents [3]. They have been widely applied as enzyme inhibitors [4,5,6,7,8]. N-chloroacetyl aminoalkylphosphonic acids [16], and the Mannich-type reactions of N-protected amino amides or aminoalkanesulfonamides, aldehydes, and phosphorus trichloride followed by hydrolysis [17,18]. Synthesis of phosphonopeptides with C-terminal aminoalkylphosphonic acids was reviewed recently [19].
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
