Sfingozin

Sfingozin
	(2S,3R)-2-aminooktadek-4-en-1,3-diol
Identifikacija
CAS registarski broj	123-78-4
PubChem	1104
ChemSpider	4444047
ChEBI	16393
ChEMBL	CHEMBL67166
Jmol-3D slike	Slika 1
SMILES
	CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
InChI
	InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14 /t17-,18 /m0/s1 ; Kod: WWUZIQQURGPMPG-KRWOKUGFSA-N InChI=1/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14 /t17-,18 /m0/s1; Kod: WWUZIQQURGPMPG-KRWOKUGFBW
Svojstva
Molekulska formula	C18H37NO2
Molarna masa	299.49 g mol−1
	(šta je ovo?) (verifikuj) ; Ukoliko nije drugačije napomenuto, podaci se odnose na standardno stanje (25 °C, 100 kPa) materijala
	Infobox references

Sfingozin (2-amino-4-oktadecen-1,3-diol) je 18-ugljenika dug amino alkohol sa nezasićenim ugljovodoničnim lancom, koji formira primarni deo sfingolipida, klase lipida ćelijske membrane koja obuhvata fosfolipid sfingomijelin.^[5]^[6]^[7]

Funkcije

Sfingozin može da bude fosforilisan in vivo putem dve kinaze, sfingozin kinaza tipa 1 i 2. To dovodi do formiranja sfingozin-1-fosfata, potentnog signalnog lipida.

Sfingolipidni metaboliti, kao što su keramid, sfingozin i sfingozin-1-fosfat, su lipidni signalni molekuli koji učestvuju u raznim ćelijskim procesima.

Sinteza

Sfingozin se sintetiše iz palmitoil CoA i serina u kondenzaciji sa intermedijerom dehidrosfingozinom.

Dehidrosfingozin se zatim redukuje NADPH-om do dihidrosfingozina (sfinganina), i zatim oksiduje FAD-om do sfingozina. Ne postoji direktan put za sintezu od sfinganina do sfingozina

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
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948863. edit
↑ Donald Voet, Judith G. Voet (2005). Biochemistry (3 izd.). Wiley. ISBN 978-0-471-19350-0.
↑ Charles Chalfant, Maurizio Del Poeta (2010). Sphingolipids as signaling and regulatory molecules (1st Ed izd.). Springer. ISBN 1441967400.
↑ Guido Tettamanti, Gianfrancesco Goracci, Abel Lajtha (2009). Handbook of Neurochemistry and Molecular Neurobiology: Neural Lipids (3rd ed izd.). Springer. 0387303456.

Spoljašnje veze

Portal Hemija

MeSH Sphingosine

[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

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948863. edit

[5] Donald Voet, Judith G. Voet (2005). Biochemistry (3 izd.). Wiley. ISBN 978-0-471-19350-0.

[6] Charles Chalfant, Maurizio Del Poeta (2010). Sphingolipids as signaling and regulatory molecules (1st Ed izd.). Springer. ISBN 1441967400.

[7] Guido Tettamanti, Gianfrancesco Goracci, Abel Lajtha (2009). Handbook of Neurochemistry and Molecular Neurobiology: Neural Lipids (3rd ed izd.). Springer. 0387303456.

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