GM1 (gangliozid)

GM1 (gangliozid)
	(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-5-hidroksi-6-(hidroksimetil)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihidroksi-6-(hidroksimetil)oksan-2-il]oksioksan-2-il]oksi-2-[(2R,3S,4R,5R,6R)-4,5-dihidroksi-6-[(E,2R,3S)-3-hidroksi-2-(ikozanoilamino)icos-4-enoksi]-2-(hidroksimetil)oksan-3-il]oksi-3-hidroksi-6-(hidroksimetil)oksan-4-il]oksi-4-hidroksi-6-[(1R,2R)-1,2,3-trihidroksipropil]oksan-2-karboksilna kiselina
Drugi nazivi	Monozialotetraheksozilgangliozid
Identifikacija
CAS registarski broj	37758-47-7
PubChem	5497107
ChemSpider	4593688
MeSH	G(M1)+Ganglioside
Jmol-3D slike	Slika 1
SMILES
	O[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H]3NC(C)=O)[C@H](O[C@@]5(C(O)=O)O[C@@]([H])([C@H](O)[C@H](O)CO)[C@H](NC(C)=O)[C@@H](O)C5)[C@H]2O)[C@@H](CO)O[C@@H](OC[C@@H]([C@@H](O)/C=C/CCCCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCCCC)=O)[C@@H]1O
InChI
	InChI=1S/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 ; Kod: QPJBWNIQKHGLAU-BVLUPYCXSA-N 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; Kod: QPJBWNIQKHGLAU-BVLUPYCXBP
Svojstva
Molekulska formula	C77H139N3O31
Molarna masa	1602.93 g mol−1
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

GM1 (monozialotetraheksozilgangliozid) je prototipni gangliozid. On je član ganglio serije gangliozida koja sadrži jedan ostatak sijalinske kiseline. GM1 ima važna fiziološka svojstava i utiče na neuronsku plastičnost i mehanizam popravke, kao i na otpuštanje neurotrofina u mozgu. Osim njegove funkcije u moždanoj fiziologiji, GM1 je mesto vezivanja kolerinog toksina i E. coli toplotno nestabilnog enterotoksina (uzročnika dijareje putnika).^[4]^[5]

Antitela za GM1 su prisutna u povišenoj koncentraciji kod obolelih od Gijen-Bareovog sindroma, demencije i lupusa, mada njihova funkcija nije jasna.^[6] Postoji evidencija koja sugeriše da su ta antitela povezana sa dijarejom kod Gijen-Bareovog sindroma.^[7]

Dodatne slike

Sfingolipidoze
Strukture GM1, GM2, GM3 gangliozida

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Mocchetti I (2005). „Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins”. Cell. Mol. Life Sci. 62 (19–20): 2283–94. DOI:10.1007/s00018-005-5188-y. PMID 16158191.
↑ Chen JC, Chang YS, Wu SL, et al. (September 2007). „Inhibition of Escherichia coli heat-labile enterotoxin-induced diarrhea by Chaenomeles speciosa”. J Ethnopharmacol 113 (2): 233–9. DOI:10.1016/j.jep.2007.05.031. PMID 17624704.
↑ Bansal AS, Abdul-Karim B, Malik RA, et al. (1994). „IgM ganglioside GM1 antibodies in patients with autoimmune disease or neuropathy, and controls”. J. Clin. Pathol. 47 (4): 300–2. DOI:10.1136/jcp.47.4.300. PMC 501930. PMID 8027366.
↑ Irie S, Saito T, Kanazawa N, et al. (1997). „Relationships between anti-ganglioside antibodies and clinical characteristics of Guillain-Barré syndrome”. Intern. Med. 36 (9): 607–12. DOI:10.2169/internalmedicine.36.607. PMID 9313102.

Spoljašnje veze

Portal Hemija

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[pmid16158191-4] Mocchetti I (2005). „Exogenous gangliosides, neuronal plasticity and repair, and the neurotrophins”. Cell. Mol. Life Sci. 62 (19–20): 2283–94. DOI:10.1007/s00018-005-5188-y. PMID 16158191.

[5] Chen JC, Chang YS, Wu SL, et al. (September 2007). „Inhibition of Escherichia coli heat-labile enterotoxin-induced diarrhea by Chaenomeles speciosa”. J Ethnopharmacol 113 (2): 233–9. DOI:10.1016/j.jep.2007.05.031. PMID 17624704.

[pmid8027366-6] Bansal AS, Abdul-Karim B, Malik RA, et al. (1994). „IgM ganglioside GM1 antibodies in patients with autoimmune disease or neuropathy, and controls”. J. Clin. Pathol. 47 (4): 300–2. DOI:10.1136/jcp.47.4.300. PMC 501930. PMID 8027366.

[pmid9313102-7] Irie S, Saito T, Kanazawa N, et al. (1997). „Relationships between anti-ganglioside antibodies and clinical characteristics of Guillain-Barré syndrome”. Intern. Med. 36 (9): 607–12. DOI:10.2169/internalmedicine.36.607. PMID 9313102.

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