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  • Catalog #:2085

  • Scientific Name:N-Hexanoyl-biotin-glucosylceramide

  • Common Name:N-C6:0-Biotin-beta-D-glucosylsphingosine; N-C6:0-Biotin-glucosylceramide

  • Empirical Formula:C40H72N4O10S

  • SDS:View Safety Data Sheet

  • Data Sheet:View Data Sheet

  • Formula Weight:801

  • Unit:5 mg

  • Solvent:none

  • Source:semisynthetic

  • Purity:98+%

  • Analytical Methods:TLC,  identity confirmed by MS

  • Natural Source:plant

  • Solubility:chloroform/methanol 2:1, methanol, DMF

  • Physical Appearance:solid

  • Storage:-20℃

  • Dry Ice:No

  • Hazardous:No


Application Notes:

N-乙酰基-生物素-葡糖神经酰胺这种葡萄糖酰基神经酰胺类似物包含一个生物素单元,通过己酸连接器连接到鞘苷部分的胺上,非常适合用于鞘脂研究。 生物素结构允许糖基神经酰胺附着在链霉亲和素上,亲和素使其在结合底物和毒素检测方面非常有用1。 糖基神经酰胺是皮肤脂质的主要成分,在层状体的形成和维持水的渗透性屏障中起重要作用。 1 .糖脑苷是非常重要的,因为它是乳糖酰胺的生物合成前体,并由此产生了大多数中性低糖脂质和神经节苷脂 脑糖苷倾向于集中在脂筏质膜的外层。 据报道,脑苷糖对酪氨酸酶(黑素生物合成的关键酶)的活性至关重要,可以引起植物的防御反应,帮助植物的质膜抵御寒冷和干旱带来的胁迫。 在戈谢氏病中,由于糖脑苷脂酶缺乏,糖脑苷脂在脾、肝、肺、骨髓和大脑中积聚 这种葡萄糖脑苷的积累与化疗耐药性有关。 葡萄糖脑苷也被证明能够调节沿内吞途径的膜运输。  

This glucosylceramide analogue contains a biotin unit attached to the amine of the sphingosine moiety via a hexanoic acid linker and is ideal for use in sphingolipid studies. The biotin structure allows for attachment of the glucosylceramide to streptavidin and avidin making it extremely useful for binding to substrates and for toxin detection1. Glucosylceramide is a major constituent of skin lipids where it has an important role in lamellar body formation and in maintaining the water permeability barrier. Glucocerebroside is very important due to its function as the biosynthetic precursor of lactosylceramide and from there of most of the neutral oligoglycolipids and gangliosides.2 Glucocerebrosides tend to be concentrated in the outer leaflet of the plasma membrane in lipid rafts. It has been reported that glucocerebrosides are essential for the activity of tyrosinase (a key enzyme in melanin biosynthesis), to elicit defense responses in plants, and to help the plasma membrane in plants to withstand stresses brought about by cold and drought. In Gaucher’s disease glucocerebrosides accumulate in the spleen, liver, lungs, bone marrow, and brain due to a deficiency of the enzyme glucocerebrosidase.3 This accumulation of glucocerebroside has been associated with chemotherapy resistance. Glucocerebroside has also been shown to be able to modulate membrane traffic along the endocytic pathway.4

1. A. Mukhopadhyay et al. “Direct interaction between the inhibitor 2 and ceramide via sphingolipid-protein binding is involved in the regulation of protein phosphatase 2A activity and signaling” FASEB, Vol. 23(3) pp. 751-763, 2009
2. D. Sillence et al. “Assay for the transbilayer distribution of glycolipids: selective oxidation of glucosylceramide to glucuronylceramide by TEMPO nitroxyl radicals” Journal of Lipid Research, Vol. 41(8) pp. 1252-1260, 2000
3. C. Walden et al. “Accumulation of Glucosylceramide in Murine Testis, Caused by Inhibition of beta-Glucosidase 2: IMPLICATIONS FOR SPERMATOGENESIS” The Journal of Biological Chemistry, Vol. 282 pp. 32655-32664, 2007
4. D. Sillence et al. “Glucosylceramide modulates membrane traffic along the endocytic pathway” Journal of Lipid Research, Vol. 43(11) pp. 1837-1845, 2002