Chemical and Chemoenzymatic Synthesis of UDP‐ N ‐Acetyl Glucosamine Probes
Abstract only Uridine‐diphosphate‐ N ‐acetylglucosamine (UDP‐GlcNAc) is a ubiquitously used nucleotide sugar involved in bacterial cell wall biosynthesis and the posttranslational modification GlcNAcylation. If functionalized versions of UDP‐GlcNAc were more easily accessible, these chemical probes...
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| Published in: | The FASEB journal Vol. 30; no. S1 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
01-04-2016
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| Online Access: | Get full text |
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| Summary: | Abstract only
Uridine‐diphosphate‐
N
‐acetylglucosamine (UDP‐GlcNAc) is a ubiquitously used nucleotide sugar involved in bacterial cell wall biosynthesis and the posttranslational modification GlcNAcylation. If functionalized versions of UDP‐GlcNAc were more easily accessible, these chemical probes could be used to rapidly investigate biological systems. However, current chemical strategies for synthesizing UDP‐GlcNAc derivatives are difficult and lengthy. Herein we describe the chemoenzymatic synthesis of strategically functionalized UDP‐GlcNAc chemical probes from Glucosamine‐1‐Phosphate (GlcN‐1‐P) and synthetic acetyl donors known as
N
‐acetylcysteamine thioesters (SNAcs) using the bacterial cell wall biosynthesis enzyme GlmU.
Hypothesis
: If GlmU is shown to use GlcN‐1‐P and derivatized SNAcs to produce modified UDP‐GlcNAc's, then these altered building blocks will be used to investigate bacterial cell wall biosynthesis and O‐GlcNAc transferase (OGT) activity.
Support or Funding Information
We would like to thank the Koh Lab and the rest of the Grimes Group for their continuing help and support. We also thank the Howard Hughes Medical Institue (HHMI), the University of Delaware's Summer Scholars program, and the Pew Foundation for funding my work. |
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| ISSN: | 0892-6638 1530-6860 |
| DOI: | 10.1096/fasebj.30.1_supplement.612.3 |