Misplaced Pages

GM2 (ganglioside): Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
Revision as of 13:59, 31 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit Latest revision as of 17:41, 5 July 2023 edit undoHeadbomb (talk | contribs)Edit filter managers, Autopatrolled, Extended confirmed users, Page movers, File movers, New page reviewers, Pending changes reviewers, Rollbackers, Template editors453,868 edits ce 
(18 intermediate revisions by 16 users not shown)
Line 1: Line 1:
{{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 = <!-- blanked - oldvalue: 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==
Line 44: Line 50:
<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>


Line 52: Line 59:
* {{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: