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{{Chembox {{Chembox
| Name = GM2
⚫ | verifiedrevid = 457965828
| Verifiedfields = changed
⚫ | verifiedrevid = 458296360
| ImageFile = GM2 ganglioside.png | ImageFile = GM2 ganglioside.png
| ImageSize = 250px | ImageSize = 250px
| ImageAlt = | ImageAlt =
| IUPACName = (2''S'',3''R'',4''E'')-3-Hydroxy-2-(octadecanoylamino)octadec-4-en-1-yl 2-acetamido-2-deoxy-β-<small>D</small>-galactopyranosyl-(1→4)--β-<small>D</small>-galactopyranosyl-(1→4)-β-<small>D</small>-glucopyranoside | IUPACName = (2''S'',3''R'',4''E'')-3-Hydroxy-2-octadecanamidooctadec-4-en-1-yl (5-acetamido-3,5-dideoxy-<small>D</small>-''glycero''-α-<small>D</small>-''galacto''-non-2-ulopyranosylonic acid)-(2→3)--β-<small>D</small>-galactopyranosyl-(1→4)-β-<small>D</small>-glucopyranoside
| SystematicName = (2''S'',4''S'',5''R'',6''R'')-5-Acetamido-2-{oxy}-6-{oxy}oxan-3-yl]oxy}-5-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-oxane-2-carboxylate
| IUPACName_hidden=yes
| OtherNames = Ganglioside GM2; Tay-Sachs ganglioside; β-<small>D</small>-GalNAc-(1→4)--β-<small>D</small>-Gal-(1→4)-β-<small>D</small>-Glc-(1↔1)-''N''-octadecanoylsphingosine | OtherNames = Ganglioside GM2; Tay–Sachs ganglioside;<br/>β-<small>D</small>-GalNAc-(1→4)--β-<small>D</small>-Gal-(1→4)-β-<small>D</small>-Glc-(1↔1)-''N''-octadecanoylsphingosine
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 19600-01-2 | CASNo = 19600-01-2
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem =
| UNII = X8HRQ6G9HF
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | PubChem = 71308211
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 26286730 | ChemSpiderID = 26286730
| 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 | 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
| 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/s1 | 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/s1
| InChIKey = USMMPBVNWHAJBE-YMEOXFOQBT | InChIKey = USMMPBVNWHAJBE-YMEOXFOQBT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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/s1 | StdInChI = 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/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = USMMPBVNWHAJBE-YMEOXFOQSA-N | StdInChIKey = USMMPBVNWHAJBE-YMEOXFOQSA-N
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 60327}} | ChEBI = 60327
}}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=67|H=121|N=3|O=26 | C=67|H=121|N=3|O=26
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility =
}}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| AutoignitionPt =
| Autoignition = }}
}}
}} }}


'''GM2''' is a type of ]. It is associated with ] such as ].<ref name="pmid18425478">{{cite journal |author=Guetta E, Peleg L |title=Rapid Detection of Fetal Mendalian Disorders: Tay-Sachs Disease |journal=] |volume=444 |issue= |pages=147–59 |year=2008 |pmid=18425478 |doi=10.1007/978-1-59745-066-9_11}}</ref> In ], '''GM2''' is a type of ]. G refers to ], the M is for monosialic (as in it has one ]), and 2 refers to the fact that it was the second monosialic ganglioside discovered. It is associated with ] such as ].<ref name="pmid18425478">{{cite book |vauthors=Guetta E, Peleg L |title=Rapid Detection of Fetal Mendalian Disorders: Tay–Sachs Disease |series=Methods in Molecular Biology |volume=444 |pages=147–59 |year=2008 |pmid=18425478 |doi=10.1007/978-1-59745-066-9_11|isbn=978-1-58829-803-4 }}</ref>


==See also== ==See also==
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<gallery> <gallery>
Image:Sphingolipidoses.svg|Sphingolipidoses Image:Sphingolipidoses.svg|Sphingolipidoses
Image:Structure of GM1, GM2, GM3.png|Structures of GM1, GM2, GM3 gangliosides
</gallery> </gallery>


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* {{MeshName|Ganglioside+GM2}} * {{MeshName|Ganglioside+GM2}}


{{biochem-stub}}
{{Sphingolipids}} {{Sphingolipids}}


Latest revision as of 17:41, 5 July 2023

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.

External links

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