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Merck
CN

900915

N-Azidoacetylgalactosamine-tetraacylated

Synonym(s):

Ac4GalNAz

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About This Item

Empirical Formula (Hill Notation):
C16H22N4O10
CAS Number:
653600-56-7
Molecular Weight:
430.37
MDL number:
MFCD26961128
UNSPSC Code:
12352116
NACRES:
NA.22

Key Documents

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InChI key

HGMISDAXLUIXKM-SROHTVIFSA-N

InChI

1S/C16H22N4O10/c1-7(21)26-6-11-14(27-8(2)22)15(28-9(3)23)13(16(30-11)29-10(4)24)19-12(25)5-18-20-17/h11,13-16H,5-6H2,1-4H3,(H,19,25)/t11?,13?,14-,15?,16+/m0/s1

SMILES string

[N+](=[N-])=NCC(=O)NC1[C@@H](OC([C@@H](C1OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C

form

powder or crystals

reaction suitability

reaction type: click chemistry

storage temp.

−20°C

Quality Level

100

Related Categories

Application

N-Azidoacetylgalactosamine-tetraacylated (Ac4GalNAz) provides the first part of a simple and robust two-step technique that helps identify and characterize cell surface sialic acid-containing glycoproteins. The azide-modified protein can be detected by reaction with alkynes. For example alkynes labeled with a fluorescent probe or a biotin can be used. The acetyl groups increase cell permeability and allow the unnatural sugars to easily pass through the cell membrane. Carboxyesterases remove the acetyl groups once the monosaccharide is in the cell.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ6347
MKCX3275
MKCV7844
MKCQ4248
MKCL3860

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Monitoring protein O-linked β-N-acetylglucosamine status via metabolic labeling and copper-free click chemistry.
Teo C F and Wells L
Analytical Biochemistry, 464, 70-72 (2014)
Probing glycosyltransferase activities with the Staudinger ligation.
Hang H C, et al.
Journal of the American Chemical Society, 126(1), 6-7 (2004)
A chemoenzymatic approach toward the preparation of site-specific antibody?drug conjugates.
Cai X and Janda K D
Tetrahedron Letters, 56(23), 3172-3175 (2015)

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