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Merck
CN

G0259

Sigma-Aldrich

D-Glucosaminic acid

≥98% (TLC)

Synonym(s):

2-Amino-2-deoxy-D-gluconic acid

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About This Item

Empirical Formula (Hill Notation):
C6H13NO6
CAS Number:
3646-68-2
Molecular Weight:
195.17
Beilstein:
1726033
EC Number:
222-879-1
MDL number:
MFCD00037764
UNSPSC Code:
12352201
PubChem Substance ID:
24895011
NACRES:
NA.25

Key Documents

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Quality Level

100

Assay

≥98% (TLC)

form

powder

optical activity

[α]20/D -15.0 to -14.0 °, c = 2.5% (w/v) in hydrochloric acid

technique(s)

thin layer chromatography (TLC): suitable

color

white to off-white

mp

235 °C

solubility

0.5 M HCl: 50 mg/mL, clear, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

N[C@H]([C@@H](O)[C@H](O)[C@H](O)CO)C(O)=O

InChI

1S/C6H13NO6/c7-3(6(12)13)5(11)4(10)2(9)1-8/h2-5,8-11H,1,7H2,(H,12,13)/t2-,3-,4-,5-/m1/s1

InChI key

UFYKDFXCZBTLOO-TXICZTDVSA-N

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Other Notes

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Storage Class Code

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
MKCP7082
MKCT4718
MKCV2954
MKCT4719
MKCJ4819

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Nanette L S Que-Gewirth et al.
The Journal of biological chemistry, 278(14), 12120-12129 (2003-01-18)
An unusual feature of the lipid A from the plant endosymbionts Rhizobium etli and Rhizobium leguminosarum is the presence of a proximal sugar unit consisting of a 2-amino-2-deoxy-gluconate moiety in place of glucosamine. An outer membrane oxidase that generates the
Fabio Pezzotti et al.
Carbohydrate research, 340(1), 139-141 (2004-12-29)
D-glucosaminic acid (2-amino-2-deoxy-D-gluconic acid), a component of bacterial lipopolysaccharides and a chiral synthon, is easily prepared on a multigram scale by air oxidation of D-glucosamine (2-amino-2-deoxy-D-glucose) catalysed by glucose oxidase.
Nanette L S Que-Gewirth et al.
The Journal of biological chemistry, 278(14), 12109-12119 (2003-01-18)
The structures of Rhizobium leguminosarum and Rhizobium etli lipid A are distinct from those found in other Gram-negative bacteria. Whereas the more typical Escherichia coli lipid A is a hexa-acylated disaccharide of glucosamine that is phosphorylated at positions 1 and
N-methyl-1-glucosaminic acid.
M L WOLFROM et al.
Journal of the American Chemical Society, 68(11), 2343-2345 (1946-11-01)
Laurent Azema et al.
Biochemical pharmacology, 67(3), 459-467 (2004-03-24)
Glucose metabolism is essential for survival of bloodstream form Trypanosoma brucei subspecies which cause human African trypanosomiasis (sleeping sickness). Hexose analogues may represent good compounds to inhibit glucose metabolism in these cells. Delivery of such compounds to the parasite is
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