A globotriaosylceramide lacking the fatty acyl group
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Lyso-Globotriaosylceramide (d18:1)

Item No. 24873

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl O-α-D-galactopyranosyl-(1→4)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
CAS Number
126550-86-5
Synonyms
  • Globotriaosylsphingosine (d18:1)
  • Lyso-Ceramide Trihexoside
  • Lyso-Gb3
Molecular Formula
C36H67NO17
Formula Weight
785.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform:Methanol:Water (2:1:0.1): SolubleChloroform:Methanol:Water (4:3:1): Soluble
SMILES
O[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@H](O[C@]3([H])[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O3)[C@H](O)[C@H]2O)[C@@H](CO)O[C@@H](OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC)[C@@H]1O
InChi Code
InChI=1S/C36H67NO17/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(41)20(37)19-49-34-30(47)27(44)32(23(17-39)51-34)54-36-31(48)28(45)33(24(18-40)52-36)53-35-29(46)26(43)25(42)22(16-38)50-35/h14-15,20-36,38-48H,2-13,16-19,37H2,1H3/b15-14+/t20-,21+,22+,23+,24+,25-,26-,27+,28+,29+,30+,31+,32+,33-,34+,35+,36-/m0/s1
InChi Key
GRGNVOCPFLXGDQ-TWHXEDJUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $754

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    Product Description

    Lyso-globotriaosylceramide is a form of globotriaosylceramide that is lacking the fatty acyl group. It binds to Shiga toxin 1 (Stx1) in the presence of cholesterol and phosphatidylcholine but does not bind Stx2.1 It also reduces viability and aggregation of human neutrophils induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) when used at concentrations of 50 and 1 μM, respectively.2 Lyso-globotriaosylceramide accumulates in the brain, heart, kidney, liver, lung, and spleen in a mouse model of Fabry disease, a lysosomal storage disorder characterized by a deficiency in the enzyme α-galactosidase A.3 It also accumulates in the urine, kidney, and plasma of patients with Fabry disease.4 Lyso-globotriaosylceramide levels decrease in response to administration of the α-galactosidase inhibitor 1-deoxygalactonojirimycin (migalastat; Item No. 17179) in a transgenic mouse model of Fabry disease. Decreases in plasma and urine concentrations of lyso-globotriaosylceramide have been used as a biomarker for efficacy of enzyme replacement therapy (ERT) and other therapies in the treatment of Fabry disease. [Matreya, LLC. Catalog No. 1520]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gallegos, K.M., Conrady, D.G., Karve, S.S., et al. Shiga toxin binding to glycolipids and glycans. PLoS One 7(2), e-30368 (2012).

    2. Fiore, S., Nicolaou, K.C., Caulfield, T., et al. Evaluation of synthetic sphingosine, lysosphingolipids and glycosphingolipids as inhibitors of functional responses of human neutrophils. Biochem. J. 266(1), 25-31 (1990).

    3. Kamani, M.A., Provençal, P., Boutin, M., et al. Glycosphingolipid storage in Fabry mice extends beyond globotriaosylceramide and is affected by ABCB1 depletion. Future Sci. OA. 2(4), FS0147 (2016).

    4. Young-Gqamana, B., Brignol, N., Chang-H.H., et al. Migalastat HCl reduces globotriaosylsphingosine (lyso-Gb3) in Fabry transgenic mice and in the plasma of Fabry patients. PLoS One 8(3), e57631 (2013).