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A7355

Sigma-Aldrich

N-Azidoacetylglucosamine, Acetylated

Synonym(s):

GlcNaz

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About This Item

Empirical Formula (Hill Notation):
C16H22N4O10
Molecular Weight:
430.37
UNSPSC Code:
12352200
PubChem Substance ID:
329770926

form

solid

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

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 Merck KGaA, Darmstadt, Germany

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Wenshuang Wang et al.
Nature communications, 11(1), 5915-5915 (2020-11-22)
Proteoglycans (PGs) are composed of a core protein and one or more chains of glycosaminoglycans (GAGs). The highly heterogeneous GAG chains play an irreplaceable role in the functions of PGs. However, the lack of an approach to control the exact
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
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
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
C R Bertozzi et al.
Science (New York, N.Y.), 291(5512), 2357-2364 (2001-03-28)
Chemical tools have proven indispensable for studies in glycobiology. Synthetic oligosaccharides and glycoconjugates provide materials for correlating structure with function. Synthetic mimics of the complex assemblies found on cell surfaces can modulate cellular interactions and are under development as therapeutic
View All Related Papers

Articles

GlycoProfile™ Azido Sugars

GlycoProfile™ Azido Sugar portfolio offers peracetylated azido sugars for glycan structure modification via chemical or biosynthetic pathways.

Glycan Labeling

Glycans play a key role in protein structure and disease; representation on cell surfaces is the glycome.

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