Synthesis of Cell-Permeable N-Acetylhexosamine 1-Phosphates
| Autor: | Emanuela Capota, Uttam K. Tambar, Badrinath N. Kakde, Jennifer J. Kohler |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
Glycoconjugate Stereochemistry Organic Chemistry Cell N acetylhexosamine Proteins Article Acetylglucosamine Phosphates chemistry.chemical_compound medicine.anatomical_structure chemistry Diazomethane Diazirine medicine Posttranslational modification Animals Stereoselectivity Glycoconjugates |
| Zdroj: | J Org Chem |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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