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MilliporeSigma

G0259

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/REAXYS Number:
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

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

11 - Combustible Solids

wgk_germany

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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Beata Liberek et al.
Carbohydrate research, 340(11), 1876-1884 (2005-06-28)
Mono- and di-N-alkylated derivatives of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucose (alkyl=methyl, ethyl, propyl, butyl, pentyl, hexyl, benzyl) were synthesised by the reductive alkylation of per-O-acetyl-d-glucosamine. (N-ethyl, N-propyl, N-butyl, N-pentyl and N-hexyl)-1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-beta-D-glucoses were deacetylated in order to attempt an enzymatic phosphorylation. All products were characterised
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
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
R L Cook et al.
The Journal of parasitology, 77(1), 21-25 (1991-02-01)
During in vitro incubation, Hymenolepsis diminuta secretes substances into the medium that inhibit DNA synthesis in the germinative region of freshly isolated, uncrowded worms. Of the many substances that are released by H. diminuta into the medium, earlier studies indicate
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