title: Convenient synthesis of phosphonodipeptides containing C-terminal α-aminoalkylphosphonic acids.
abstract: 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.
authors.affiliation: State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing, 100029, China.
authors.forename: Biyun
authors.initials: B
authors.lastname: Sun
authors.affiliation: State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing, 100029, China.
authors.forename: Jiaxi
authors.initials: J
authors.lastname: Xu
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D002712:Chlorides / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D006801:Humans; D006868:Hydrolysis; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D057786:Peptidomimetics / Q000138:chemical synthesis*; D010757:Phosphorous Acids / Q000737:chemistry*; D017553:Phosphorus Compounds / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000577:Amides; D000900:Anti-Bacterial Agents; D002712:Chlorides; D004791:Enzyme Inhibitors; D010455:Peptides; D057786:Peptidomimetics; D010757:Phosphorous Acids; D017553:Phosphorus Compounds; C043693:phosphorus chloride
keywords: Amino acid amide; Mannich reaction; phosphonopeptide; synthesis