For research use only. Not for therapeutic Use.
Gangliosides are formed from a glycosphingolipid combined with one or more sialic acids at the oligosaccharide chain. They are anchored at the outer surface of the plasma membrane where they pack densely with cholesterol to form lipid microdomains that modulate both intra-<wbr></wbr> and inter-<wbr></wbr>cellular signaling events. Ganglioside G<sub>Q1b</sub> is a tetrasialoganglioside that is characterized by having two sialic residues linked to the inner galactose unit. At 5 nM, it can stimulate an ecto-<wbr></wbr>type (cell-<wbr></wbr>surface) protein phosphorylation system in the human neuroblastoma cell line GOTO. Ganglioside G<sub>Q1b</sub> has been reported to promote neurite outgrowth during early neuronal differentiation by activating the ERK1/2 MAP kinase pathway. It has also been shown to initiate keratinocyte differentiation through phophoinositide turnover.
| Catalog Number | R065082 |
| CAS Number | 68652-37-9 |
| Synonyms | ganglioside GQ1b, tetrasodium salt |
| Molecular Formula | C106H194N10O56 |
| Purity | ≥95% |
| Storage | -20°C |
| IUPAC Name | (2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4R,5R,6R)-3-acetamido-5-[(2S,3R,4S,5S,6R)-4-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-6-[(1S,2R)-2-[(2S,4S,5R,6R)-2-carboxy-4-hydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-4-hydroxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2R,3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-4-hydroxyoxane-2-carboxylic acid;azane |
| InChI | InChI=1S/C106H182N6O56.4H3N/c1-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-69(133)111-55(56(126)35-33-31-29-27-25-23-20-18-16-14-12-10-8-2)50-153-96-83(142)81(140)87(66(46-118)156-96)159-97-84(143)82(141)86(67(47-119)157-97)158-95-75(110-54(6)125)93(167-105(101(149)150)39-58(128)72(108-52(4)123)91(165-105)79(138)64(44-116)161-103(99(145)146)37-57(127)71(107-51(3)122)89(163-103)76(135)61(131)41-113)88(68(48-120)155-95)160-98-85(144)94(78(137)63(43-115)154-98)168-106(102(151)152)40-59(129)73(109-53(5)124)92(166-106)80(139)65(45-117)162-104(100(147)148)38-60(130)74(112-70(134)49-121)90(164-104)77(136)62(132)42-114;;;;/h33,35,55-68,71-98,113-121,126-132,135-144H,7-32,34,36-50H2,1-6H3,(H,107,122)(H,108,123)(H,109,124)(H,110,125)(H,111,133)(H,112,134)(H,145,146)(H,147,148)(H,149,150)(H,151,152);4*1H3/b35-33+;;;;/t55-,56+,57-,58-,59-,60-,61+,62+,63+,64+,65+,66+,67+,68+,71+,72+,73+,74+,75+,76+,77+,78-,79+,80+,81+,82+,83+,84+,85+,86-,87+,88-,89+,90+,91+,92+,93+,94-,95-,96+,97-,98-,103+,104+,105-,106-;;;;/m0..../s1 |
| InChIKey | IOULOLQJODJAEM-BSALKOQBSA-N |
| SMILES | CCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)OC5(CC(C(C(O5)C(C(CO)OC6(CC(C(C(O6)C(C(CO)O)O)NC(=O)CO)O)C(=O)O)O)NC(=O)C)O)C(=O)O)O)OC7(CC(C(C(O7)C(C(CO)OC8(CC(C(C(O8)C(C(CO)O)O)NC(=O)C)O)C(=O)O)O)NC(=O)C)O)C(=O)O)NC(=O)C)O)O)O)O)C(C=CCCCCCCCCCCCCC)O.N.N.N.N |
| Reference | 1.Tsuji, S.,Yamashita, T., and Nagai, Y. A novel, carbohydrate signal-mediated cell surface protein phosphorylation: Ganglioside GQ1b stimulates ecto-protein kinase activity on the cell surface of a human neuroblastoma cell line, GOTO. Journal of Biochemi |
