N-Hexanoyl-biotin-monosialoganglioside GM1/N-乙酰基-生物素-单唾液酸神经节苷脂GM1

Specifications

• Catalog #:2053

• Scientific Name:N-Hexanoyl-biotin-monosialoganglioside GM₁

• Common Name:Biotin-C6:0-GM₁

• Empirical Formula:C₇₁H₁₂₂N₆O₃₃S•NH₃

• SDS:View Safety Data Sheet

• Data Sheet:View Data Sheet

• Formula Weight:1620 +NH₃

• Unit:500 µg

• Source:semisynthetic, bovine

• Purity:98+%

• Analytical Methods:TLC; identity confirmed by MS

• Solubility:chloroform/methanol/water, 2:1:0.1

• Physical Appearance:solid

• Storage:-20℃

• Dry Ice:No

• Hazardous:No

Description

Application Notes:

N-乙酰基-生物素-单唾液酸神经节苷脂GM1是神经节苷脂GM1类似物含有一个生物素单元，通过己酸连接子连接到鞘氨醇部分的胺上，非常适合用于神经节苷脂研究。 生物素结构允许神经节苷脂附着到链霉亲和素和亲和素底物，使其在结合底物和毒素检测方面非常有用。 神经节苷脂是含有一种或多种唾液酸的酸性鞘糖脂，通常在细胞膜的外层形成脂筏，特别是在中枢神经系统的神经细胞中。 它们参与许多细胞活动，包括增殖、分化、黏附、信号转导、细胞间相互作用、肿瘤发生和转移 神经节苷脂的积累与多种疾病有关，包括泰-萨克斯病和山德霍夫病，而对神经节苷脂的自身免疫反应可导致格林-巴利综合征。 神经节苷脂作为各种毒素和细菌的受体，在各种肿瘤中积累，并协助许多神经功能。 因此，它们在治疗过程中非常重要，需要进行大量的研究。 GM1通过与神经生长因子(NGF)的高亲和力酪氨酸激酶型受体Trk直接紧密结合，刺激神经元萌发，增强神经生长因子(NGF)的作用。 GM1也被鉴定为霍乱毒素的特异性细胞表面受体，使其成为治疗干预的重要靶点。  

This ganglioside GM₁ analogue contains a biotin unit attached to the amine of the sphingosine moiety via a hexanoic acid linker and is ideal for use in ganglioside studies. The biotin structure allows for attachment of the ganglioside to streptavidin and avidin substrates making it extremely useful for binding to substrates and for toxin detection.¹Gangliosides are acidic glycosphingolipids containing one or more sialic acids that generally form lipid rafts in the outer leaflet of the cell plasma membrane, especially in neuronal cells in the central nervous system.^2,3 They participate in many cellular activities including proliferation, differentiation, adhesion, signal transduction, cell-to-cell interactions, tumorigenesis, and metastasis.⁴ The accumulation of gangliosides has been linked to several diseases including Tay-Sachs and Sandhoff disease while an autoimmune response against gangliosides can lead to Guillain-Barre syndrome. Gangliosides act as receptors for various toxins and bacteria, accumulate in various tumors, and aid in many neuronal functions. They are therefore very important in therapeutic processes and have warranted much research. GM₁ stimulates neuronal sprouting and enhances the action of nerve growth factor (NGF) by directly and tightly associating with Trk, the high-affinity tyrosine kinase-type receptor for NGF. GM₁ has also been identified as the specific cell surface receptor for cholera toxin making it an important target for therapeutic interventions.5

References:
1. A. Pukin et al. Chemoenzymatic synthesis of biotin-appended analogues of gangliosides GM₂, GM₁, GD_1a and GalNAc-GD_1a for solid-phase applications and improved ELISA tests. Org. Biomol. Chem., 9(16):5809-5815, 2011
2. L. Svennerholm, et al. (eds.), Structure and Function of Gangliosides, New York, Plenum, 1980
3. T. Kolter, R. Proia, K. Sandhoff, Combinatorial Ganglioside Biosynthesis. J. Biol. Chem., July Vol. 277, No. 29, pp. 25859-25862, 2002
4. S. Birkle, G. Zeng, L. Gao, R. K. Yu, and J. Aubry. Role of tumor-associated gangliosides in cancer progression. Biochimie, 85, 455–463, 2003
5. C. E. Miller, J. Majewski, R. Faller, S. Satija, and T. L. Kuhl, Cholera Toxin Assault on Lipid Monolayers Containing Ganglioside GM₁. Biophysj., June Vol. 86(6), 3700–3708, 2004