Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

G0259

Sigma-Aldrich

D-Glucosaminic acid

≥98% (TLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

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

Looking for similar products? Visit Product Comparison Guide

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
N-methyl-1-glucosaminic acid.
M L WOLFROM et al.
Journal of the American Chemical Society, 68(11), 2343-2345 (1946-11-01)
D Horton et al.
Carbohydrate research, 193, 49-60 (1989-10-31)
Acetylation of 2-amino-2-deoxy-D-gluconic acid (1) with acetyl chloride-pyridine gave 2,3-unsaturated six- and five-membered lactones (2 and 3). Their benzoylated analogs (4 and 5) were obtained by benzoylation of 1 with benzoyl chloride-pyridine. Reaction of 1 with hot acetic anhydride-sodium acetate
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service