Triptofan
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| Imena | |
|---|---|
| IUPAC ime
triptofan
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| Druga imena
2-amino-3-(1H-indol-3-il)propanojska kislina
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| Identifikatorji | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.000.723 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Lastnosti | |
| C11H12N2O2 | |
| Molska masa | 204,23 g·mol−1 |
| 0,23 g/L pri 0 °C, 11,4 g/L pri 25 °C, | |
| Topnost | Topen v vročem alkoholu, alkalnih hidroksidih, netopen v kloroformu. |
| Kislost (pKa) | 2,38 (karboksil), 9,39 (amino)[1] |
| Farmakologija | |
| N06AX02 (WHO) | |
Če ni navedeno drugače, podatki veljajo za material v standardnem stanju pri 25 °C, 100 kPa). | |
| Sklici infopolja | |
Triptofan (skrajšano Trp ali W) je nepolarna in aromatska aminokislina s formulo C11H12N2O2. Sodi med esencialne aminokisline, torej je človek ne more sam sintetizirati, zato jo lahko dobimo samo s prehrano. Je tudi proteinogena aminokislina, ki jo kodira le en kodon, UGG.
Triptofan je prekurzor za nevrotransmitorja serotonin in melatonin.[2]
Zgodovina
Prvi je triptofan izoliral in opisal Frederick Hopkins leta 1901.[3] Iz 600 g kazeina je po hidrolizi pridobil 4-8 g triptofana.[4]
Biosinteza
Mikroorganizmi in rastline so sposobni sami sintetizirati triptofan, medtem ko ga živali dobijo s prehrano, običajno v obliki proteinov. Običajni poti sinteze sta iz šikimske ali iz antranilne kisline.[5] V zadnjem koraku sinteze encim triptofan sintaza katalizira reakcijo med indolom in serinom.
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Viri
- ↑ Dawson, RMC; in sod. (1969). Data for Biochemical Research. Oxford: Clarendon Press. ISBN 0-19-855338-2.
- ↑ Slominski, Andrzej; Semak, Igor; Pisarchik, Alexander; Sweatman, Trevor; Szczesniewski, Andre; Wortsman, Jacobo. »Conversion of L-tryptophan to serotonin and melatonin in human melanoma cells«. FEBS Letters. 511 (1–3): 102–106. doi:10.1016/s0014-5793(01)03319-1.
- ↑ Hopkins FG; Cole SW (december 1901). »A contribution to the chemistry of proteids: Part I. A preliminary study of a hitherto undescribed product of tryptic digestion«. The Journal of Physiology. 27 (4–5): 418–28. doi:10.1113/jphysiol.1901.sp000880. PMC 1540554. PMID 16992614.
{{navedi časopis}}: Vzdrževanje CS1: samodejni prevod datuma (povezava) - ↑ Cox GJ, King H (1943). »L-Tryptophane«. Org. Synth. 2: 612–616. doi:10.15227/orgsyn.010.0100.
- ↑ Radwanski ER; Last RL (Julij 1995). »Tryptophan biosynthesis and metabolism: biochemical and molecular genetics«. The Plant Cell. 7 (7): 921–34. doi:10.1105/tpc.7.7.921. PMC 160888. PMID 7640526.
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