Sun Biyun, Xu Jiaxi
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing, 100029, China.
J Pept Sci. 2015 Jul;21(7):615-9. doi: 10.1002/psc.2785. Epub 2015 May 21.
Phosphonopeptides are important phosphorus analogs of natural peptides and have been widely applied as enzyme inhibitors and antibacterial agents. A series of phosphonodipeptides containing C-terminal α-aminoalkylphosphonic acids was synthesized in satisfactory to good yields conveniently from 2-(N-benzyloxycarbonylamino)alkanamides, aldehydes, and phosphorus trichloride via Mannich-type reaction and subsequent sequential hydrolysis. The reaction mechanism was proposed and verified by (31)P NMR tracing experiments. The current method is an efficient and convenient method for preparation of phosphonopeptides containing C-terminal α-aminoalkylphosphonic acids.
膦肽是天然肽的重要磷类似物，已被广泛用作酶抑制剂和抗菌剂。通过曼尼希型反应及随后的顺序水解，以2-(N-苄氧羰基氨基)链烷酰胺、醛和三氯化磷为原料，方便地合成了一系列含有C端α-氨基烷基膦酸的膦二肽，产率令人满意至良好。通过(31)P NMR追踪实验提出并验证了反应机理。该方法是制备含有C端α-氨基烷基膦酸的膦肽的一种高效便捷的方法。
