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43659

Sigma-Aldrich

Glucosylsphingosine

≥98.0% (TLC)

Synonym(s):

(2S,3R,4E)-2-Amino-3-hydroxy-4-octadecen-1-yl β-D-glucopyranoside, 1-β-D-Glucosylsphingosine, Glucosyl-C18-sphingosine

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About This Item

Empirical Formula (Hill Notation):
C24H47NO7
CAS Number:
52050-17-6
Molecular Weight:
461.63
Beilstein/REAXYS Number:
4333674
UNSPSC Code:
12352211
PubChem Substance ID:
329756364
NACRES:
NA.85

Quality Level

100

assay

≥98.0% (TLC)

form

powder

lipid type

sphingolipids

Storage temp.

−20°C

SMILES string

O[C@@H]1[C@@H](O)[C@H](OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC)O[C@H](CO)[C@H]1O

InChI

1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20?,21+,22+,23?,24+/m0/s1

Inchi Key

HHJTWTPUPVQKNA-JLRUQHRASA-N

Biochem/physiol Actions

Glucosylsphingosine is a cytotoxic compound. Accumulation of glucosylsphingosine in brain and other tissues occurs in patients with Gaucher disease, which is an inherited deficiency of lysosomal glucocerebrosidase, which converts glucosylsphingosine to glucose and sphingosine.

Storage Class

11 - Combustible Solids

wgk_germany

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’.

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Wujuan Zhang et al.
The Analyst, 142(18), 3380-3387 (2017-08-16)
Gaucher disease (GD) is caused by mutations on the GBA1 gene leading to deficiency in acid β-glucosidase (GCase) and subsequent accumulation of its substrates, glucosylceramide (GlcC) and glucosylsphingosine (GlcS). GlcS in plasma has been proposed as a highly sensitive and
Chengfang Tang et al.
Clinical biochemistry, 87, 79-84 (2020-11-15)
Gaucher disease (GD) is caused by a deficiency of β-glucosidase (GCase), leading to accumulation of glucosylceramide (GlcC) and glucosylsphingosine (Lyso-Gb1). Lyso-Gb1 is a reliable biomarker for GD. This study aims to develop a simple, effective and accurate method for the
Jingwen Hu et al.
Mikrochimica acta, 187(7), 373-373 (2020-06-07)
A new series of 9-plex chemical isotope-labeling reagents, levofloxacin-based mass tags (LMTs) named as LMT359, 360, 361, 362, 363, 373, 375, 376, and 378, was firstly designed and synthesized for the high-throughput labeling of globotriaosylsphingosine (lyso-Gb3), a disease biomarker of
E Beutler
Blood reviews, 2(1), 59-70 (1988-03-01)
Gaucher disease is a glycolipid storage disorder characterized by accumulation of glucocerebroside in the liver, spleen, and bones, and caused by a deficiency of glucocerebrosidase. Glucocerebrosidase cDNA has been cloned and sequenced, and much has been learned about the synthesis
Ellen Sidransky
Molecular genetics and metabolism, 83(1-2), 6-15 (2004-10-07)
Gaucher disease, the recessively inherited deficiency of the enzyme glucocerebrosidase and the most common sphingolipidosis, has both non-neurological and neuronopathic forms and a continuum of diverse clinical manifestations. Studies of genotype-phenotype correlations reveal significant genotypic heterogeneity among clinically similar patients
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