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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

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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.
E T Zavras et al.
The Journal of parasitology, 70(6), 937-944 (1984-12-01)
It was shown previously that worm-conditioned saline (WCS) prepared from crowded 10-day-old H. diminuta inhibited the incorporation of 3H-thymidine into DNA in the anterior regions of uncrowded worms and that the inhibition was partially accounted for by succinate and acetate
Kenji Sasaki et al.
Bioorganic & medicinal chemistry, 12(6), 1367-1375 (2004-03-17)
Biological activity of N-acetyl-6-sulfo-beta-d-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/1/71 H3N2). pNP 6-Sulfo-GlcNAc 1a was proved to
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
U R Bhat et al.
The Journal of biological chemistry, 269(20), 14402-14410 (1994-05-20)
The structure of lipid A from the lipopolysaccharide of Rhizobium leguminosarum bv. phaseoli (wild type strain CE3) was investigated by alkylation analysis, nuclear magnetic resonance spectroscopy, and electrospray and fast atom bombardment mass spectrometry of the de-O-acylated lipid A. The
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