Convenient synthesis of phosphonodipeptides containing C-terminal α-aminoalkylphosphonic acids

Biyun Sun, Jiaxi Xu*

*Corresponding author for this work

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 31P NMR tracing experiments. The current method is an efficient and convenient method for preparation of phosphonopeptides containing C-terminal α-aminoalkylphosphonic acids.

Original languageEnglish
Pages (from-to)615-619
Number of pages5
JournalJournal of Peptide Science
Volume21
Issue number7
DOIs
Publication statusPublished - 1 Jul 2015
Externally publishedYes

Keywords

  • Amino acid amide
  • Mannich reaction
  • phosphonopeptide
  • synthesis

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