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GM2 (ganglioside)

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GM2
Names
IUPAC name (2S,3R,4E)-3-Hydroxy-2-octadecanamidooctadec-4-en-1-yl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2→3)--β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
Systematic IUPAC name (2S,4S,5R,6R)-5-Acetamido-2-{oxy}-6-{oxy}oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-oxane-2-carboxylate
Other names Ganglioside GM2; Tay–Sachs ganglioside;
β-D-GalNAc-(1→4)--β-D-Gal-(1→4)-β-D-Glc-(1↔1)-N-octadecanoylsphingosine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C68H123N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-51(81)71-44(45(78)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-90-65-58(86)57(85)60(49(38-74)93-65)95-66-59(87)63(61(50(39-75)94-66)96-64-53(70-43(4)77)56(84)55(83)48(37-73)92-64)91-41-68(67(88)89)35-46(79)52(69-42(3)76)62(97-68)54(82)47(80)36-72/h31,33,44-50,52-66,72-75,78-80,82-87H,5-30,32,34-41H2,1-4H3,(H,69,76)(H,70,77)(H,71,81)(H,88,89)/b33-31+/t44-,45+,46-,47+,48+,49+,50+,52+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63+,64-,65-,66-,68-/m1/s1Key: USMMPBVNWHAJBE-YMEOXFOQSA-N
  • InChI=1/C68H123N3O26/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-51(81)71-44(45(78)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-90-65-58(86)57(85)60(49(38-74)93-65)95-66-59(87)63(61(50(39-75)94-66)96-64-53(70-43(4)77)56(84)55(83)48(37-73)92-64)91-41-68(67(88)89)35-46(79)52(69-42(3)76)62(97-68)54(82)47(80)36-72/h31,33,44-50,52-66,72-75,78-80,82-87H,5-30,32,34-41H2,1-4H3,(H,69,76)(H,70,77)(H,71,81)(H,88,89)/b33-31+/t44-,45+,46-,47+,48+,49+,50+,52+,53+,54+,55-,56+,57+,58+,59+,60+,61-,62+,63+,64-,65-,66-,68-/m1/s1Key: USMMPBVNWHAJBE-YMEOXFOQBT
SMILES
  • CCCCCCCCCCCCCCCCCC(=O)N(CO1((((O1)CO)O2((((O2)CO)O3((((O3)CO)O)O)NC(=O)C)OC4(C(((O4)((CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)(/C=C/CCCCCCCCCCCCC)O
Properties
Chemical formula C67H121N3O26
Molar mass 1384.700 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

In organic chemistry, GM2 is a type of ganglioside. G refers to ganglioside, the M is for monosialic (as in it has one sialic acid), and 2 refers to the fact that it was the second monosialic ganglioside discovered. It is associated with GM2 gangliosidoses such as Tay–Sachs disease.

See also

Additional images

  • Sphingolipidoses Sphingolipidoses
  • Structures of GM1, GM2, GM3 gangliosides Structures of GM1, GM2, GM3 gangliosides

References

  1. Guetta E, Peleg L (2008). Rapid Detection of Fetal Mendalian Disorders: Tay–Sachs Disease. Methods in Molecular Biology. Vol. 444. pp. 147–59. doi:10.1007/978-1-59745-066-9_11. ISBN 978-1-58829-803-4. PMID 18425478. {{cite book}}: |journal= ignored (help)

External links

Glycoconjugates, lipids, and glycolipids: sphingolipids and glycosphingolipids, and metabolic intermediates
Simple glycosphingolipids
Globosides
Gangliosides
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