A7355

Sigma-Aldrich

N-Azidoacetylglucosamine, Acetylated

Synonym(s):
GlcNaz
Empirical Formula (Hill Notation):
C16H22N4O10
Molecular Weight:
430.37
PubChem Substance ID:

storage temp.

2-8°C

SMILES string

CC(=O)OC[C@H]1OC(OC(C)=O)[C@H](NC(=O)N=[N+]=[N-])[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI

1S/C15H20N4O10/c1-6(20)25-5-10-12(26-7(2)21)13(27-8(3)22)11(17-15(24)18-19-16)14(29-10)28-9(4)23/h10-14H,5H2,1-4H3,(H,17,24)/t10-,11-,12-,13-,14?/m1/s1

InChI key

MRRKYEUMMAEYHG-GNMOMJPPSA-N

Related Categories

Application

An unnatural azido sugar that can be introduced metabolically in model organisms and subsequently incorporates in glycan structures. The azide group will react with phosphines linked to agents for visualization or selective capture. To be used in conjunction with the GlycoProfile™ FLAG®-Phosphine (GPHOS1) that is compatible with many additional FLAG tools for both applications.

Legal Information

FLAG is a registered trademark of Sigma-Aldrich Co. LLC

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

null
Eiichi Hashimoto et al.
iScience, 23(7), 101299-101299 (2020-07-08)
The proteasome is a therapeutic target in cancer, but resistance to proteasome inhibitors often develops owing to the induction of compensatory pathways. Through a genome-wide siRNA screen combined with RNA sequencing analysis, we identified hexokinase and downstream O-GlcNAcylation as cell...
Sudharsana R Ande et al.
PloS one, 4(2), e4586-e4586 (2009-02-25)
Prohibitin (PHB or PHB1) is an evolutionarily conserved, multifunctional protein which is present in various cellular compartments including the plasma membrane. However, mechanisms involved in various functions of PHB are not fully explored yet. Here we report for the first...
Yubo Liu et al.
Scientific reports, 7(1), 12334-12334 (2017-09-28)
O-GlcNAc transferase (OGT) plays an important role in regulating numerous cellular processes through reversible post-translational modification of nuclear and cytoplasmic proteins. However, the function of O-GlcNAcylation is still not well understood. Cell permeable OGT inhibitors are needed to manipulate O-GlcNAcylation...
Jennifer A Prescher et al.
Nature, 430(7002), 873-877 (2004-08-20)
Cell surfaces are endowed with biological functionality designed to mediate extracellular communication. The cell-surface repertoire can be expanded to include abiotic functionality through the biosynthetic introduction of unnatural sugars into cellular glycans, a process termed metabolic oligosaccharide engineering. This technique...
Articles
Structural modifications of proteins are essential to living cells. When aberrantly regulated they are often the basis of disease. Glycans are responsible for much of the structural variation in biologic systems, and their representation on cell surfaces is commonly called the “glycome.”
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Related Content
The GlycoProfile™ Azido Sugar portfolio consists of three peracetylated azido sugars that may be incorporated into glycan structures chemically or by using existing biosynthetic pathways of mammalian cells.
Read More

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