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Ornithine

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Title: Ornithine  
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Subject: Urea cycle, Alkaloid, Gramicidin S, Arginine, Non-proteinogenic amino acids
Collection: Basic Amino Acids, Urea Cycle
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Ornithine

L-Ornithine
Names
IUPAC name
L-Ornithine
Other names
(+)-(S)-2,5-Diaminovaleric acid, (+)-(S)-2,5-Diaminopentanoic acid
Identifiers
 Y
ChEBI  N
ChEMBL  Y
ChemSpider  Y
DrugBank  N
EC number 200-731-7
Jmol-3D images Image
KEGG  Y
MeSH
PubChem
UNII  Y
Properties[1]
C5H12N2O2
Molar mass 132.16 g/mol
Melting point 140 °C (284 °F; 413 K)
soluble
Solubility soluble in ethanol
Acidity (pKa) 1.94
Chiral rotation ([α]D)
+11.5 (H2O, c = 6.5)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

Ornithine is a non proteinogenic amino acid that plays a role in the urea cycle. Ornithine is abnormally accumulated in the body in ornithine transcarbamylase deficiency.

Contents

  • Role in urea cycle 1
  • Other reactions 2
  • Potential medical uses 3
    • Exercise fatigue 3.1
    • Cirrhosis 3.2
    • Weightlifting supplement 3.3
  • References 4
  • External links 5

Role in urea cycle

L-Ornithine is one of the products of the action of the enzyme arginase on L-arginine, creating urea. Therefore, ornithine is a central part of the urea cycle, which allows for the disposal of excess nitrogen. Ornithine is recycled and, in a manner, is a catalyst. First, ammonia is converted into carbamoyl phosphate (phosphate-CONH2). Ornithine is converted into a urea derivative at the δ (terminal) nitrogen by carbamoyl phosphate. Another nitrogen is added from aspartate, producing the denitrogenated fumarate, and the resulting arginine (a guanidinium compound) is hydrolysed back to ornithine, producing urea. The nitrogens of urea come from the ammonia and aspartate, and the nitrogen in ornithine remains intact.

Ornithine lactamization

Ornithine is not an amino acid coded for by DNA, that is, not proteinogenic. 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.[2]

Other reactions

Ornithine, via the action of ornithine decarboxylase (E.C. 4.1.1.17), is the starting point for the synthesis of polyamines such as putrescine.

In bacteria, such as E. coli, ornithine can be synthesized from L-glutamate.[3]

Ornithine is also the starting point for cocaine biosynthesis, when decarboxylated, then modified greatly by cytochrome P450.

Potential medical uses

Exercise fatigue

L-Ornithine supplementation attenuated fatigue in subjects in a placebo-controlled study using a cycle ergometer. The results suggested that L-ornithine has an antifatigue effect in increasing the efficiency of energy consumption and promoting the excretion of ammonia.[4][5]

Cirrhosis

L-Ornithine L-aspartate (LOLA), a stable salt of ornithine and aspartic acid, has been used in the treatment of cirrhosis.[6]

Weightlifting supplement

Amino acid supplements, including L-ornithine, are frequently marketed to bodybuilders and weightlifters through the claim that it will increase levels of human growth hormone (HGH). However, clinical study has shown that these supplements do not increase levels of HGH with low dose (2 grams per day divided into two doses) supplementation.[7]

References

  1. ^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-408.  .
  2. ^ Arthur L. Weber and Stanley L. Miller (1981). "Reasons for the Occurrence of the Twenty Coded Protein Amino Acids" (PDF). J. Mol. Evol. 17 (5): 273–284.  
  3. ^ "Ornithine Biosynthesis". School of Biological and Chemical Sciences, Queen Mary, University of London. Retrieved 2007-08-17 .
  4. ^ Sugino, T; Shirai, T; Kajimoto, Y; Kajimoto, O (2008). "L-ornithine supplementation attenuates physical fatigue in healthy volunteers by modulating lipid and amino acid metabolism". Nutrition research 28 (11): 738–43.  
  5. ^ Demura, S; Yamada, T; Yamaji, S; Komatsu, M; Morishita, K (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.  
  6. ^ Sikorska, H; Cianciara, J; Wiercińska-Drapało, A (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 : organ Polskiego Towarzystwa Lekarskiego 28 (168): 490–5.  
  7. ^ Fogelholm; Näveri, HK; Kiilavuori, KT; Härkönen, MH; et al. (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): 290–297.  

External links

  • Ornithine MS Spectrum
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