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49130

Sigma-Aldrich

D-(+)-Glucosamine hydrochloride

≥99.0% (HPLC)

Synonym(s):

2-Amino-2-deoxy-D-glucose hydrochloride, Chitosamine hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C6H13NO5 · HCl
CAS Number:
66-84-2
Molecular Weight:
215.63
Beilstein:
4157370
EC Number:
200-638-1
MDL number:
MFCD00135831
UNSPSC Code:
12352201

Assay

≥99.0% (HPLC)

optical activity

[α]20/D +72.5±2°, 24 hr, c = 2% in H2O

ign. residue

≤0.05%

mp

190-194 °C (dec.) (lit.)
≥300 °C

solubility

H2O: 0.1 g/mL, clear, colorless

SMILES string

Cl.N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI

1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6?;/m1./s1

InChI key

QKPLRMLTKYXDST-NSEZLWDYSA-N

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Biochem/physiol Actions

Glucosamine, an amino sugar, is the precursor of the hexosamine biosynthetic pathway leading to the formation of UDP-N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids. D-(+)-Glucosamine inhibits the coaggregation of Candida yeast species with the bacterial strain S. salivarius.

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Oshra Betzer et al.
ACS nano, 8(9), 9274-9285 (2014-08-19)
A critical problem in the development and implementation of stem cell-based therapy is the lack of reliable, noninvasive means to image and trace the cells post-transplantation and evaluate their biodistribution, final fate, and functionality. In this study, we developed a
Ji-Sun Hwang et al.
Metabolism: clinical and experimental, 64(3), 368-379 (2014-12-18)
This study investigated the potential of glucosamine (GlcN) to affect body weight gain and insulin sensitivity in mice normal and at risk for developing diabetes. Male C57BL/6J mice were fed either chow diet (CD) or a high fat diet (HFD)
Khadijeh Jamialahmadi et al.
Environmental toxicology and pharmacology, 38(1), 212-219 (2014-06-25)
Glucosamine (GlcN) is an important precursor in the biochemical synthesis of glycosylated proteins and lipids in human body. It gains importance because of its contribution to human health and its multiple biological and therapeutic effects. In this study, the in
Tali Ilovitsh et al.
Biomedical optics express, 6(4), 1262-1272 (2015-04-25)
Localization microscopy provides valuable insights into cellular structures and is a rapidly developing field. The precision is mainly limited by additive noise and the requirement for single molecule imaging that dictates a low density of activated emitters in the field
Han Na Suh et al.
Journal of cellular physiology, 229(10), 1557-1568 (2014-03-05)
The aim of this study is to determine whether GlcN could recover the endoplasmic reticulum (ER) stress-induced dysfunction of Na(+) /glucose cotransporter (SGLT) in renal proximal tubule cells (PTCs) under hypoxia. With the rabbit model, the renal ischemia induced tubulointerstitial
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