@article{eba7398a200b42aa9a53992320bf16c2,
title = "Synthesis of Cell-Permeable N-Acetylhexosamine 1-Phosphates",
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.",
author = "Kakde, {Badrinath N.} and Emanuela Capota and Kohler, {Jennifer J.} and Tambar, {Uttam K.}",
note = "Funding Information: The authors acknowledge support from the Welch Foundation (I-1686 and I-1748), the National Institutes of Health (U01CA242115 and R01GM102604), a W. W. Caruth, Jr. Endowed Scholarship, and a Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV). The authors thank Han Wu for assistance with HPAEC-PAD analysis. The authors acknowledge the Shimadzu Center for Advanced Analytical Chemistry (SCAAC) at The University of Texas at Arlington for HRMS data. The authors also thank our diverse collection of lab members for creating an environment that supported the success of this project. Publisher Copyright: {\textcopyright} 2021 American Chemical Society",
year = "2021",
month = dec,
day = "17",
doi = "10.1021/acs.joc.1c01781",
language = "English (US)",
volume = "86",
pages = "18257--18264",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "24",
}