Ac4ManNDAz

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Description: Photo-crosslinking probe for studying glycoproteins and glycolipids
Chemical Name: 2-Deoxy-2-[[3-(3-methyl-3H-diazirin-3-yl)-1-oxopropyl]amino]-D-mannopyranose-1,3,4,6-tetraacetate
Purity: ≥98% (HPLC)
Datasheet
Citations
Reviews

Biological Activity for Ac4ManNDAz

Ac4ManNDAz is a cell-permeable photo-crosslinking probe for studying glycoprotein or glycolipid interactions. The compound is an unnatural diazirine-containing monosaccharide building block, which acts as a photo-crosslinker. Once inside the cell, Ac4ManNDAz is metabolized and incorporated into cell surface glycoproteins as a photo-crosslinking sialic acid analog. Upon UV irradiation, the diazirine group is activated to a reactive carbene that covalently crosslinks to nearby molecules.

Technical Data for Ac4ManNDAz

M. Wt 457.44
Formula C19H27N3O10
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 1015698-39-1
PubChem ID 122400676
InChI Key UZYLHDJBFVVKBM-GAMQSXCYSA-N
Smiles CC(OC[C@H]1OC([C@H]([C@H]([C@@H]1OC(C)=O)OC(C)=O)NC(CCC2(N=N2)C)=O)OC(C)=O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for Ac4ManNDAz

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
ethanol 45.74 100
DMSO 45.74 100

Preparing Stock Solutions for Ac4ManNDAz

The following data is based on the product molecular weight 457.44. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.19 mL 10.93 mL 21.86 mL
5 mM 0.44 mL 2.19 mL 4.37 mL
10 mM 0.22 mL 1.09 mL 2.19 mL
50 mM 0.04 mL 0.22 mL 0.44 mL

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References for Ac4ManNDAz

References are publications that support the biological activity of the product.

Tanaka et al (2008) Photoactivatable crosslinking sugars for capturing glycoprotein interactions. J.Am.Chem.Soc. 130 3278 PMID: 18293988

Bond et al (2009) Photocrosslinking of glycoconjugates using metabolically incorporated diazirine-containing sugars. Nat.Protoc. 4 1044 PMID: 19536272

Bond et al (2011) Metabolism of diazirine-modified N-acetylmannosamine analogues to photo-cross-linking sialosides. Bioconjug.Chem. 22 1811 PMID: 21838313

Cervin et al (2018) GM1 ganglioside-independent intoxication by Cholera toxin. PLoS.Pathog. 14 e1006862 PMID: 29432456


If you know of a relevant reference for Ac4ManNDAz, please let us know.

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Citations for Ac4ManNDAz

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