Asialo GM1 ganglioside | CAS# 71012-19-6 | cellular lipid raft component

MedKoo Cat#: 575053 | Name: Asialo GM1 ganglioside

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Asialo GM1 ganglioside is a component of cellular lipid rafts and can be formed by the cleavage of the sialic acid residue from ganglioside GM1 by neuraminidase. Ganglioside GM1 asialo is a glycolipid receptor for P. aeruginosa flagellin and stimulates defensive responses in host cells, including extracellular ATP release, calcium mobilization, and ERK1/2 phosphorylation when stimulated by flagellin and an anti-ganglioside GM1 asialo antibody. The percentage of ganglioside GM1 asialo-positive natural killer (NK) and CD8+ T cells in lung is increased in a mouse model of respiratory syncytial virus (RSV) infection compared with healthy animals. Depletion of ganglioside GM1 asialo-positive NK and T cells reduces IFN-γ levels in the lung, reduces weight loss, and increases lung viral load in RSV-infected mice. Ganglioside GM1 asialo mixture contains ganglioside GM1 asialo molecular species with C18:1 and C20:1 sphingoid backbones.

Chemical Structure

Asialo GM1 ganglioside

CAS#71012-19-6

Theoretical Analysis

MedKoo Cat#: 575053

Name: Asialo GM1 ganglioside

CAS#: 71012-19-6

Chemical Formula: C62H114N2O23

Exact Mass: 1254.7812

Molecular Weight: 1255.58

Elemental Analysis: C, 59.31; H, 9.15; N, 2.23; O, 29.31

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 850.00	2 Weeks

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Synonym

Asialo GM1 ganglioside; Asialo GM1 Mixture; ASGM1 Mixture; Gangliotetraosylceramide Mixture; Ganglioside GM1 Asialo Mixture

IUPAC/Chemical Name

N-((2S,3R,E)-1-(((2R,3R,4R,5S,6R)-5-(((2S,3R,4R,5R,6R)-5-(((2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-hydroxyoctadec-4-en-2-yl)stearamide

InChi Key

VELGMVLNORPMAO-HMWOVMCASA-N

InChi Code

InChI=1S/C62H114N2O23/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(71)64-40(41(70)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-80-60-54(78)51(75)57(44(36-67)83-60)86-62-55(79)52(76)56(45(37-68)84-62)85-59-47(63-39(3)69)58(49(73)43(35-66)81-59)87

SMILES Code

[H][C@](CO[C@@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O[C@@H]3O[C@@H]([C@@H]([C@@H]([C@H]3NC(C)=O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)CO)O)O)CO)([C@](O)(/C=C/CCCCCCCCCCCCC)[H])NC(CCCCCCCCCCCCCCCCC)=O

Appearance

A lyophilized powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,255.58 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Chiricozzi E, Di Biase E, Lunghi G, Fazzari M, Loberto N, Aureli M, Mauri L, Sonnino S. Turning the spotlight on the oligosaccharide chain of GM1 ganglioside. Glycoconj J. 2021 Feb;38(1):101-117. doi: 10.1007/s10719-021-09974-y. Epub 2021 Feb 23. PMID: 33620588; PMCID: PMC7917043. 2: Ogawa G, Kaida K, Kusunoki S, Ueda M, Kimura F, Kamakura K. Antibodies to ganglioside complexes consisting of asialo-GM1 and GQ1b or GT1a in Fisher and Guillain-Barré syndromes. J Neuroimmunol. 2009 Sep 29;214(1-2):125-7. doi: 10.1016/j.jneuroim.2009.06.017. Epub 2009 Jul 24. PMID: 19631994. 3: Patil PD, Jin Y, Luk YY. Chemical control over Asialo-GM1: A dual ligand for pili and Lectin A that activates swarming motility and facilitates adherence of Pseudomonas aeruginosa. Colloids Surf B Biointerfaces. 2022 Jul;215:112478. doi: 10.1016/j.colsurfb.2022.112478. Epub 2022 Mar 24. PMID: 35390596. 4: Sillerud LO, Yu RK. Comparison of the 13C-N.M.R. spectra of gangliosides GM1 with those of GM1-oligosaccharide and asialo-GM1. Carbohydr Res. 1983 Mar 1;113(2):173-88. doi: 10.1016/0008-6215(83)88234-2. PMID: 6839313. 5: Tanaka M. [Asialo GM1]. Nihon Rinsho. 2004 Dec;62 Suppl 12:797-9. Japanese. PMID: 15658453. 6: Park HJ, Jhon GJ, Han SJ, Kang YK. Conformational study of asialo-GM1 (GA1) ganglioside. Biopolymers. 1997;42(1):19-35. doi: 10.1002/(SICI)1097-0282(199707)42:1<19::AID-BIP3>3.0.CO;2-4. PMID: 9209156. 7: Nakahara K. [Asialo GM1]. Nihon Rinsho. 1995 Mar;53 Su Pt 2:195-7. Japanese. PMID: 8753215. 8: Tanaka M. [Asialo GM1]. Nihon Rinsho. 1999 Sep;57 Suppl:827-9. Japanese. PMID: 10543248. 9: de Bentzmann S, Roger P, Dupuit F, Bajolet-Laudinat O, Fuchey C, Plotkowski MC, Puchelle E. Asialo GM1 is a receptor for Pseudomonas aeruginosa adherence to regenerating respiratory epithelial cells. Infect Immun. 1996 May;64(5):1582-8. doi: 10.1128/iai.64.5.1582-1588.1996. PMID: 8613364; PMCID: PMC173965. 10: Cheshev PE, Khatuntseva EA, Tsvetkov IuE, Shashkov AS, Nifant'ev NE. Sintez aminoétilglikozidov oligosakharidnykh tsepeĭ gangliozidov GM1 i asialo-GM1 [Synthesis of aminoethylglycosides with oligosaccharide GM1 and asialo-GM1 ganglioside chains]. Bioorg Khim. 2004 Jan-Feb;30(1):68-79. Russian. doi: 10.1023/b:rubi.0000015775.24385.a0. PMID: 15040306. 11: Cossy Isasi S, Fernandez AR, Paglini P, Bronia DH. GM1 ganglioside induced myocardial restoration and survival of mice with experimental Chagas' disease. Acta Trop. 1999 Oct 15;73(3):295-302. doi: 10.1016/s0001-706x(99)00030-3. PMID: 10546847. 12: Thygesen P, Hougen HP, Christensen HB, Rygaard J, Svendsen O, Juul P. Anti- asialo GM1 antibodies prevents guanethidine-induced sympathectomy in athymic rats. Immunopharmacol Immunotoxicol. 1992;14(1-2):219-32. doi: 10.3109/08923979209009221. PMID: 1597655. 13: Karupiah G, Blanden RV. Anti-asialo-GM1 inhibits vaccinia virus infection of murine ovaries: asialo-GM1 as an additional virus receptor? Immunol Cell Biol. 1990 Oct;68 ( Pt 5):343-6. doi: 10.1038/icb.1990.46. PMID: 2083955. 14: Ahmed K, Suzuki Y, Miyamoto D, Nagatake T. Asialo-GM1 and asialo-GM2 are putative adhesion molecules for Moraxella catarrhalis. Med Microbiol Immunol. 2002 May;191(1):5-10. doi: 10.1007/s00430-002-0109-2. PMID: 12137200. 15: Rock P, Allietta M, Young WW Jr, Thompson TE, Tillack TW. Ganglioside GM1 and asialo-GM1 at low concentration are preferentially incorporated into the gel phase in two-component, two-phase phosphatidylcholine bilayers. Biochemistry. 1991 Jan 8;30(1):19-25. doi: 10.1021/bi00215a003. PMID: 1988021. 16: Maruyama T, Watanabe K, Takei I, Kasuga A, Shimada A, Yanagawa T, Kasatani T, Suzuki Y, Kataoka K, Saruta, et al. Anti-asialo GM1 antibody suppression of cyclophosphamide-induced diabetes in NOD mice. Diabetes Res. 1991 May;17(1):37-41. PMID: 1823558. 17: Baba H, Daune GC, Ilyas AA, Pestronk A, Cornblath DR, Chaudhry V, Griffin JW, Quarles RH. Anti-GM1 ganglioside antibodies with differing fine specificities in patients with multifocal motor neuropathy. J Neuroimmunol. 1989 Dec;25(2-3):143-50. doi: 10.1016/0165-5728(89)90131-8. PMID: 2584393. 18: Rodi PM, Maggio B, Bagatolli LA. Direct visualization of the lateral structure of giant vesicles composed of pseudo-binary mixtures of sulfatide, asialo-GM1 and GM1 with POPC. Biochim Biophys Acta Biomembr. 2018 Feb;1860(2):544-555. doi: 10.1016/j.bbamem.2017.10.022. Epub 2017 Nov 27. PMID: 29106974. 19: Kamata K, Mizutani K, Takahashi K, Marchetti R, Silipo A, Addy C, Park SY, Fujii Y, Fujita H, Konuma T, Ikegami T, Ozeki Y, Tame JRH. The structure of SeviL, a GM1b/asialo-GM1 binding R-type lectin from the mussel Mytilisepta virgata. Sci Rep. 2020 Dec 16;10(1):22102. doi: 10.1038/s41598-020-78926-7. PMID: 33328520; PMCID: PMC7744527. 20: Liao B, Kamiya-Matsuoka C, Fang X, Smith RG, Shanina E. Alternating ptosis associated with asialo-GM1 and GD1b antibodies. Int J Neurosci. 2016 Dec;126(12):1139-41. doi: 10.3109/00207454.2015.1136825. Epub 2016 Jan 25. PMID: 26710925.