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49746

Sigma-Aldrich

Anthrose

≥98.0% (TLC)

Synonym(s):

4,6-Dideoxy-4-(3-hydroxy-3-methylbutanamido)-2-O-methyl-D-glucopyranose

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About This Item

Empirical Formula (Hill Notation):
C12H23NO6
CAS Number:
769959-88-8
Molecular Weight:
277.31
UNSPSC Code:
12352201
PubChem Substance ID:
329757517
NACRES:
NA.25

assay

≥98.0% (TLC)

form

solid

storage temp.

−20°C

SMILES string

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

InChI

1S/C11H21NO6/c1-5-7(8(14)9(15)10(16)18-5)12-6(13)4-11(2,3)17/h5,7-10,14-17H,4H2,1-3H3,(H,12,13)/t5-,7-,8+,9-,10?/m1/s1

InChI key

UUVASJJCLBEXCO-QNRYFBKSSA-N

Application

Anthrose, a nonreducing dideoxy-glucopyranose, has recently been identified as a unique component of the bacillus anthracis exosporium and Bacillus cereus endospores. Anthrose is used in anthrax research.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

To gain a comprehensive understanding of our extensive range of Oligosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCBC0738
BCBC0738V
1387410

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Rina Saksena et al.
Carbohydrate research, 340(9), 1591-1600 (2005-06-01)
The key step in the first chemical synthesis of anthrose (16) and its methyl alpha- (6) and beta-glycoside (22) was inversion of configuration at C-2 in triflates 10, 2, and 18, respectively, obtained from the common intermediate, methyl 4-azido-3-O-benzyl-4,6-dideoxy-alpha-D-mannopyranoside (1).
Rachel L Kubiak et al.
Biochemistry, 51(4), 867-878 (2012-01-10)
The unusual dideoxy sugar d-anthrose has been identified as an important component in the endospores of infectious agents such as Bacillus anthracis and Bacillus cereus. Specifically, it is the terminal sugar on the bacterium's exosporium, and it provides a point
James M Daubenspeck et al.
The Journal of biological chemistry, 279(30), 30945-30953 (2004-05-21)
Spores of Bacillus anthracis, the causative agent of anthrax, are enclosed by a prominent loose fitting layer called the exosporium. The exosporium consists of a basal layer and an external hairlike nap. The filaments of the nap are composed of
John G Bruno et al.
Journal of fluorescence, 22(3), 915-924 (2012-01-06)
A library of 92 DNA aptamer sequences was developed against Bacillus anthracis (nonpathogenic Sterne strain) spores and anthrose sugar immobilized on magnetic beads. The selected DNA sequences were studied for similarities and potential binding pockets between the B. anthracis spore
Michael H Norris et al.
PLoS biology, 18(12), e3001052-e3001052 (2020-12-29)
Bacillus anthracis, a spore-forming gram-positive bacterium, causes anthrax. The external surface of the exosporium is coated with glycosylated proteins. The sugar additions are capped with the unique monosaccharide anthrose. The West African Group (WAG) B. anthracis have mutations rendering them
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