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Ornithine

From Wikipedia, the free encyclopedia
l-Ornithine
Names
IUPAC name
L-Ornithine
Other names
(+)-(S)-2,5-Diaminovaleric acid
(+)-(S)-2,5-Diaminopentanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.000.665Edit this at Wikidata
EC Number
  • 200-731-7
KEGG
MeSHOrnithine
UNII
  • InChI=1S/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1 checkY
    Key: AHLPHDHHMVZTML-BYPYZUCNSA-N checkY
  • InChI=1/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
  • InChI=1/C5H12N2O2/c6-3-1-2-4(7)5(8)9/h4H,1-3,6-7H2,(H,8,9)/t4-/m0/s1
    Key: AHLPHDHHMVZTML-BYPYZUCNBZ
  • O=C(O)[C@@H](N)CCCN
Properties[1]
C5H12N2O2
Molar mass132.16 g/mol
Melting point140 °C (284 °F; 413 K)
soluble
Solubilitysoluble inethanol
Acidity (pKa)1.94
+11.5 (H2O,c = 6.5)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Ornithine is anon-proteinogenic α-amino acid that plays a role in theurea cycle. Ornithine is abnormally accumulated in the body inornithine transcarbamylase deficiency. Theradical isornithyl.[2]

Role in urea cycle

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L-Ornithine is one of the products of the action of the enzymearginase onL-arginine, creatingurea. Therefore, ornithine is a central part of the urea cycle, which allows for the disposal of excessnitrogen. Ornithine is recycled and, in a manner, is a catalyst. First, ammonia is converted intocarbamoyl phosphate (H
2
NC(O)OPO2−
3
) bycarbamoyl phosphate synthetase.Ornithine transcarbamylase catalyzes the reaction between carbamoyl phosphate and ornithine to formcitrulline and phosphate (Pi). Anotheramino group is added fromaspartate, producing arginine and denitrogenatedfumarate. The resulting arginine (aguanidinium compound) is hydrolysed back to ornithine, producing urea. The amino groups of urea come from the ammonia and aspartate, and the nitrogen in ornithine remains intact.

Reaction mechanism:. Theside-chain amino group of ornithine (Orn) attacks the carbonyl carbon of carbamoyl phosphate (CP) nucleophilically,left, to form a tetrahedral transition state,middle. Charge rearrangement releases citrulline (Cit) and phosphate (Pi),right.[3]

Ornithine is not an amino acid coded for byDNA, that is, notproteinogenic. However, in mammalian non-hepatic tissues, the main use of the urea cycle is in arginine biosynthesis, so, as an intermediate in metabolic processes, ornithine is quite important.[4]

Other reactions

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Ornithine, via the action ofornithine decarboxylase (E.C. 4.1.1.17), is the starting point for the synthesis ofpolyamines such asputrescine.

In bacteria, such asE. coli, ornithine can be synthesized fromL-glutamate.[5]

Ornithine lactamization

Research

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Exercise fatigue

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L-Ornithine supplementation attenuated fatigue in subjects in a placebo-controlled study using a cycle ergometer. The results suggested thatL-ornithine has an antifatigue effect in increasing the efficiency of energy consumption and promoting the excretion of ammonia.[6][7]

Weightlifting supplement

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Amino acid supplements, includingL-ornithine, are frequently marketed to bodybuilders and weightlifters with claims for increasing levels ofhuman growth hormone (HGH), muscle mass, and strength. A 1993 short 4-day clinical study reported thatL-ornithine in combination withL-arginine andL-lysine at 2 g/d each did not increase HGH.[8] A review from 2002 on the topic concluded "The use of specific amino acids to stimulate GH release by athletes is not recommended."[9]

Cirrhosis

[edit]

L-OrnithineL-aspartate (LOLA), a stable salt of ornithine and aspartic acid, has been used in the treatment ofcirrhosis[10] andhepatic encephalopathy.[11]

See also

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References

[edit]
  1. ^Weast, Robert C., ed. (1981).CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, Florida: CRC Press. p. C-408.ISBN 0-8493-0462-8.
  2. ^Sivashanmugam M (February 2017). "Ornithine and its role in metabolic diseases: An appraisal".Biomed Pharmacother.86:185–194.doi:10.1016/j.biopha.2016.12.024.PMID 27978498.
  3. ^Langley DB, Templeton MD, Fields BA, Mitchell RE, Collyer CA (June 2000)."Mechanism of inactivation of ornithine transcarbamoylase by Ndelta -(N'-Sulfodiaminophosphinyl)-L-ornithine, a true transition state analogue? Crystal structure and implications for catalytic mechanism".The Journal of Biological Chemistry.275 (26):20012–9.doi:10.1074/jbc.M000585200.PMID 10747936.
  4. ^Weber AL, Miller SL (1981)."Reasons for the occurrence of the twenty coded protein amino acids"(PDF).Journal of Molecular Evolution.17 (5):273–84.Bibcode:1981JMolE..17..273W.doi:10.1007/BF01795749.PMID 7277510.S2CID 27957755.
  5. ^"Ornithine Biosynthesis". School of Biological and Chemical Sciences, Queen Mary, University of London. Archived fromthe original on 2012-04-14. Retrieved2007-08-17.
  6. ^Sugino T, Shirai T, Kajimoto Y, Kajimoto O (November 2008). "L-ornithine supplementation attenuates physical fatigue in healthy volunteers by modulating lipid and amino acid metabolism".Nutrition Research.28 (11):738–43.doi:10.1016/j.nutres.2008.08.008.PMID 19083482.
  7. ^Demura S, Yamada T, Yamaji S, Komatsu M, Morishita K (October 2010)."The effect of L-ornithine hydrochloride ingestion on performance during incremental exhaustive ergometer bicycle exercise and ammonia metabolism during and after exercise".European Journal of Clinical Nutrition.64 (10):1166–71.doi:10.1038/ejcn.2010.149.hdl:2297/25434.PMID 20717126.
  8. ^Fogelholm GM, Näveri HK, Kiilavuori KT, Härkönen MH (September 1993). "Low-dose amino acid supplementation: no effects on serum human growth hormone and insulin in male weightlifters".International Journal of Sport Nutrition.3 (3):290–7.doi:10.1123/ijsn.3.3.290.PMID 8220394.
  9. ^Chromiak JA, Antonio J (2002). "Use of amino acids as growth hormone-releasing agents by athletes".Nutrition.18 (7–8):657–61.doi:10.1016/s0899-9007(02)00807-9.PMID 12093449.
  10. ^Sikorska H, Cianciara J, Wiercińska-Drapało A (June 2010)."[Physiological functions of L-ornithine and L-aspartate in the body and the efficacy of administration of L-ornithine-L-aspartate in conditions of relative deficiency]".Polski Merkuriusz Lekarski (in Polish).28 (168):490–5.PMID 20642112. Retrieved10 March 2025 – via ResearchGate.
  11. ^Butterworth R, McPhail M (February 2019)."L-Ornithine L-Aspartate (LOLA) for Hepatic Encephalopathy in Cirrhosis: Results of Randomized Controlled Trials and Meta-Analyses".Drugs.79 (Suppl 1):31–37.doi:10.1007/s40265-018-1024-1.PMC 6416237.PMID 30706425.

External links

[edit]
Wikimedia Commons has media related toL-Ornithine.
Kacetyl-CoA
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