State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, China.
Molecules. 2020 Dec 12;25(24):5894. doi: 10.3390/molecules25245894.
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.
膦肽是肽的磷类似物，已被广泛用作酶抑制剂和抗原，以诱导催化抗体。膦肽通常含有一个氨基烷基膦酸残基，包括 C 末端氨基烷基膦酸的膦肽和具有膦酰胺键的膦肽。膦肽中的膦酰胺键通常通过膦酰氯与膦酰化、与偶联试剂和酶的缩合以及磷酰化后氧化形成。酰胺、醛、二烷基二氯膦酸和氨基/肽酯的拟四组分缩合反应是通过同时构建氨基烷基膦酸和形成膦酰胺键来合成膦肽的一种替代、收敛和有效的策略。本文重点介绍了含有膦酰胺键的膦肽的合成方法。
