Synthesis of Cell-Permeable N-Acetylhexosamine 1-Phosphates

Badrinath N. Kakde, Emanuela Capota, Jennifer J. Kohler, Uttam K. Tambar

Research output: Contribution to journalArticlepeer-review

Abstract

We recently reported the incorporation of diazirine photo-cross-linkers onto the O-GlcNAc posttranslational modification in mammalian cells, enabling the identification of binding partners of O-GlcNAcylated proteins. Unfortunately, the syntheses of the diazirine-functionalized substrates have exhibited inconsistent yields. We report a robust and stereoselective synthesis of cell-permeable GlcNAc-1-phosphate esters based on the use of commercially available bis(diisopropylamino)chlorophosphine. We demonstrate this approach for two diazirine-containing GlcNAc analogues, and we report the cellular incorporation of these compounds into glycoconjugates to support photo-cross-linking applications.

Original languageEnglish (US)
Pages (from-to)18257-18264
Number of pages8
JournalJournal of Organic Chemistry
Volume86
Issue number24
DOIs
StatePublished - Dec 17 2021

ASJC Scopus subject areas

  • Organic Chemistry

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