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{{Short description|Biochemical compound important in the brain and intestines}} |
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{{Context|date=October 2009}} |
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{{About|the neural compound|the engine boosting compound|GM-1}} |
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{{About|the neural compound|the engine boosting compound|GM-1|the MIDI standard|General MIDI}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 421946867 |
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| verifiedrevid = 455199468 |
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| ImageFile = GM1 ganglioside.png |
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| ImageFile = GM1 ganglioside.png |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| IUPACName = (2''S'',4''S'',5''R'',6''R'')-5-acetamido-2-oxyoxan-2-yl]oxy-2--2-(hydroxymethyl)oxan-3-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-oxane-2-carboxylic acid |
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| IUPACName = (2''S'',4''S'',5''R'',6''R'')-5-acetamido-2-oxyoxan-2-yl]oxy-2--2-(hydroxymethyl)oxan-3-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-oxane-2-carboxylic acid |
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| IUPACName_hidden = yes |
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| OtherNames = Monosialotetrahexosylganglioside |
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| OtherNames = Monosialotetrahexosylganglioside |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4593688 |
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| ChemSpiderID = 4593688 |
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| InChI = 1/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b33-31+/t44?,45?,46-,47?,48+,49+,50+,51+,53+,54+,55?,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66-,67+,68-,69+,70-,71-,73-/m0/s1 |
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| InChI = 1/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(87)76-44(45(84)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-98-69-61(94)59(92)63(50(39-80)101-69)103-71-62(95)67(107-73(72(96)97)35-46(85)53(74-42(3)82)66(106-73)55(88)47(86)36-77)64(51(40-81)102-71)104-68-54(75-43(4)83)65(57(90)49(38-79)99-68)105-70-60(93)58(91)56(89)48(37-78)100-70/h31,33,44-51,53-71,77-81,84-86,88-95H,5-30,32,34-41H2,1-4H3,(H,74,82)(H,75,83)(H,76,87)(H,96,97)/b33-31+/t44?,45?,46-,47?,48+,49+,50+,51+,53+,54+,55?,56-,57-,58-,59+,60+,61+,62+,63+,64-,65+,66-,67+,68-,69+,70-,71-,73-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QPJBWNIQKHGLAU-BVLUPYCXSA-N |
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| StdInChIKey = QPJBWNIQKHGLAU-BVLUPYCXSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 37758-47-7 |
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| CASNo = 37758-47-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 5497107 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES = O1(O2O(CO)(O3O(CO)(O)(O4O(CO)(O)(O)4O)3NC(C)=O)(O5(C(O)=O)O()((O)(O)CO)(NC(C)=O)(O)C5)2O)(CO)O(OC((O)/C=C/CCCCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCCCC)=O)1O |
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| UNII = A763JQ77KX |
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| MeSHName = G(M1)+Ganglioside |
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| PubChem = 5497107 |
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| SMILES = O1(O2O(CO)(O3O(CO)(O)(O4O(CO)(O)(O)4O)3NC(C)=O)(O5(C(O)=O)O()((O)(O)CO)(NC(C)=O)(O)C5)2O)(CO)O(OC((O)/C=C/CCCCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCCCC)=O)1O |
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| MeSHName = G(M1)+Ganglioside |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=77|H=139|N=3|O=31 |
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| C=77 | H=139 | N=3 | O=31 |
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| Appearance = |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| Solubility = |
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'''GM1''' (monosialotetrahexosylganglioside) the "prototype" ], is a member of the ganglio series of gangliosides which contain one ] residue. GM1 has important ] properties and impacts ] and repair mechanisms, and the release of ] in the ]. Besides its function in the physiology of the brain, GM1 acts as the site of binding for both ] and ] ] (]).<ref name="pmid16158191">{{cite journal | author = Mocchetti I | title = Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins | journal = Cell. Mol. Life Sci. | volume = 62 | issue = 19–20 | pages = 2283–94 | year = 2005 | pmid = 16158191 | doi = 10.1007/s00018-005-5188-y}}</ref><ref>{{cite journal |author=Chen JC, Chang YS, Wu SL, ''et al.'' |title=Inhibition of Escherichia coli heat-labile enterotoxin-induced diarrhea by Chaenomeles speciosa |journal=J Ethnopharmacol |volume=113 |issue=2 |pages=233–9 |year=2007 |month=September |pmid=17624704 |doi=10.1016/j.jep.2007.05.031 }}</ref> |
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'''GM1''' ('''monosialotetrahexosylganglioside''') the "prototype" ], is a member of the ganglio series of gangliosides which contain one ] residue. GM1 has important ] properties and impacts ] and repair mechanisms, and the release of ] in the ]. Besides its function in the physiology of the brain, GM1 acts as the site of binding for both ] and ] ] (]).<ref name="pmid16158191">{{cite journal | author = Mocchetti I | title = Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins | journal = Cell. Mol. Life Sci. | volume = 62 | issue = 19–20 | pages = 2283–94 | year = 2005 | pmid = 16158191 | doi = 10.1007/s00018-005-5188-y| pmc = 11139125 }}</ref><ref>{{cite journal |vauthors=Chen JC, Chang YS, Wu SL |title=Inhibition of Escherichia coli heat-labile enterotoxin-induced diarrhea by Chaenomeles speciosa |journal=J Ethnopharmacol |volume=113 |issue=2 |pages=233–9 |date=September 2007 |pmid=17624704 |doi=10.1016/j.jep.2007.05.031 |display-authors=etal}}</ref> |
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==GM1 and inherited disease== |
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] are increased in ], ] and ] but their function is not clear.<ref name="pmid8027366">{{cite journal | author = Bansal AS, Abdul-Karim B, Malik RA, ''et al.'' | title = IgM ganglioside GM1 antibodies in patients with autoimmune disease or neuropathy, and controls | journal = J. Clin. Pathol. | volume = 47 | issue = 4 | pages = 300–2 | year = 1994 | pmid = 8027366 | doi =10.1136/jcp.47.4.300 | pmc = 501930 }}</ref> There is some evidence to suggest these antibodies are associated with ] in ].<ref name="pmid9313102">{{cite journal | author = Irie S, Saito T, Kanazawa N, ''et al.'' | title = Relationships between anti-ganglioside antibodies and clinical characteristics of Guillain-Barré syndrome | journal = Intern. Med. | volume = 36 | issue = 9 | pages = 607–12 | year = 1997 | pmid = 9313102 | doi =10.2169/internalmedicine.36.607 }}</ref> |
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Galactosidases are enzymes that break down GM1, and the failure to remove GM1 results in GM1 gangliosidosis.<ref>{{cite web|last=U.S. National Library of Medicine|title=GM1 gangliosidosis|url=http://ghr.nlm.nih.gov/condition/gm1-gangliosidosis|publisher=Genetic Home Reference|accessdate=26 October 2013}}</ref> GM1 gangliosidosis are inherited disorders that progressively destroy neurons in the brain and spinal cord as GM1 accumulates. Without treatment, this results in developmental decline and muscle weakness, eventually leading to severe retardation and death. |
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==GM1 and acquired disease== |
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] are increased in ], ] and ] but their function is not clear.<ref name="pmid8027366">{{cite journal |vauthors=Bansal AS, Abdul-Karim B, Malik RA | title = IgM ganglioside GM1 antibodies in patients with autoimmune disease or neuropathy, and controls | journal = J. Clin. Pathol. | volume = 47 | issue = 4 | pages = 300–2 | year = 1994 | pmid = 8027366 | doi =10.1136/jcp.47.4.300 | pmc = 501930 |display-authors=etal}}</ref> There is some evidence to suggest antibodies against GM1 are associated with ] in Guillain–Barré syndrome.<ref name="pmid9313102">{{cite journal |vauthors=Irie S, Saito T, Kanazawa N | title = Relationships between anti-ganglioside antibodies and clinical characteristics of Guillain–Barré syndrome | journal = Intern. Med. | volume = 36 | issue = 9 | pages = 607–12 | year = 1997 | pmid = 9313102 | doi =10.2169/internalmedicine.36.607 |display-authors=etal| doi-access = free }}</ref> |
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GM1 antibodies are also seen in ], a rare antibody-mediated inflammatory neuropathy. |
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==GM1 and the cholera toxin== |
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==GM1 and the cholera toxin== |
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The bacteria ] produces a multimeric toxin called the ]. The A1 subunit of this toxin will gain entry to intestinal epithelial cells with the assistance of the B subunit via the GM1 ganglioside receptor. Once inside, the A1 subunit will ADP ribosylate the ] Alpha subunit which will prevent its ] activity. This will lock it in the active state and it will continuously stimulate adenylate cyclase. The sustained adenylate cyclase activity will lead to a sustained increase of ] which will cause electrolyte and water loss, causing ].{{Citation needed|date=September 2007}} |
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The bacteria ] produces a multimeric toxin called the ]. The secreted toxin attaches to the surface of the host mucosa cell by binding to GM1 gangliosides. GM1 consists of a sialic acid-containing oligosaccharide covalently attached to a ceramide lipid. The A1 subunit of this toxin will gain entry to intestinal epithelial cells with the assistance of the B subunit via the GM1 ganglioside receptor. Once inside, the A1 subunit will ADP ribosylate the ], which will prevent its ] activity. This will lock it in the active state and it will continuously stimulate adenylate cyclase. The sustained adenylate cyclase activity will lead to a sustained increase of ] which will cause electrolyte and water loss, causing ].{{Citation needed|date=September 2007}} |
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Fortunately, the ] receptor is present in the small intestine. When the cholera patient is given a solution containing water, ] and ], the SGLT1 receptor will reabsorb sodium and glucose, while water will be passively absorbed with the sodium. This will replace the water and ] loss in the cholera induced diarrhea. |
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The ] receptor is present in the small intestine. When the cholera patient is given a solution containing water, ] and ], the SGLT1 receptor will reabsorb sodium and glucose, while water will be passively absorbed with the sodium. This will replace the water and ] loss in the cholera-induced diarrhea. |
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==Therapeutic applications== |
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Because of GM1's close role in neuron repair mechanisms, it has been investigated as a possible drug to slow or even reverse the progression of a wide range of ]. Controlled ] studies have indicated that GM1 can ease the symptoms of ], presumably by countering degeneration of the ],<ref>{{cite web|last=Thomas Jefferson University|title=GM1 Ganglioside Effects on Parkinson's Disease|url=http://clinicaltrials.gov/show/NCT00037830|publisher=Clinical Trials.gov|date=December 2012}}</ref> and a similar methodology has been pursued to try and limit cellular damage from ] and ] occurring after acute ].<ref>{{cite journal|last=McDonald|first=John|title=Repairing the Damaged Spinal Cord|journal=Scientific American|date=September 1999|page=69}}</ref> |
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==Additional images== |
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==Additional images== |
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<gallery> |
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<gallery> |
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Image:Sphingolipidoses.svg|Sphingolipidoses |
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Image:Sphingolipidoses.svg|Sphingolipidoses |
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Image:Structure of GM1, GM2, GM3.png|Structures of GM1, GM2, GM3 ]s |
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</gallery> |
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</gallery> |
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{{Sphingolipids}} |
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{{biochem-stub}} |
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