A convenient procedure for the solid-phase synthesis of hydroxamic acids on PEGA resins

Nitin Subhash Nandurkar, Rico Petersen, Katrine Qvortrup, Vitaly V. Komnatnyy, Kennedy Taveras, Sebastian Thordal Le Quement, Robin Frauenlob, Michael Givskov, Thomas Eiland Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

An efficient method for the solid-phase synthesis of hydroxamic acids is described. The method comprises the nucleophilic displacement of esters immobilized on PEGA resins with hydroxylamine/sodium hydroxide in isopropanol. The hydroxyaminolysis protocol is compatible with a broad range of PEGA-supported peptide and peptidomimetic esters. The methodology was found to be compatible with two new strategies for the synthesis of solid-supported lactams and diketopiperazines, respectively, both relying on the high inter- and intramolecular reactivity of cyclic N-acyliminium ions with electron-rich aromatics and heteroaromatics, ultimately affording hydroxamic acid derivatives in high purities.
Original languageEnglish
JournalTetrahedron Letters
Volume52
Issue number52
Pages (from-to)7121-7124
ISSN0040-4039
DOIs
Publication statusPublished - 2011

Keywords

  • Hydroxylamine
  • PEGA resin
  • Solid-phase synthesis
  • HDAC inhibitor
  • Hydroxamic acids

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