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Information about Ornithine

Ornithine
IUPAC name2,5-diaminopentanoic acid
Identifiers
CAS number70-26-8
PubChem389
MeSHOrnithine
SMILESC(CC(C(=O)O)N)CN
Properties
Molecular formulaC5H12N2O2
Molar mass132.161
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)
Ornithine is an amino acid, whose structure is:

NH2-CH2-CH2-CH2-CHNH2-COOH

Role in urea cycle

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 not an amino acid coded for by DNA, and in that sense, is not involved in protein synthesis. 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.

Lactamization

Enlarge picture
Ornithine lactamization
It is believed to not be a part of genetic code because polypeptides containing unprotected ornithines undergo spontaneous lactamization. This proved to be a problem when ornithine was artificially incorporated in 21st amino acid systems.

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.[1]

References

1. ^ Ornithine Biosynthesis. Retrieved on 2007-08-17.
IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. It is developed and kept up to date under the auspices of the International Union of Pure and Applied Chemistry (IUPAC).
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CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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PubChem is a database of chemical molecules. The system is maintained by the National Center for Biotechnology Information (NCBI), a component of the National Library of Medicine, which is part of the United States National Institutes of Health (NIH).
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Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. Created and updated by the United States National Library of Medicine (NLM), it is used by the MEDLINE/PubMed
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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standard state of a material is its state at 1 bar (100 kilopascals exactly). This pressure was changed from 1 atm (101.325 kilopascals) by IUPAC in 1990.[1] The standard state of a material can be defined at any given temperature, most commonly 25 degrees Celsius,
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amino acid is a molecule that contains both amine and carboxyl functional groups. In biochemistry, this term refers to alpha-amino acids with the general formula H2NCHRCOOH, where R is an organic substituent.
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3, 5, 4, 2
(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1

Atomic radius 65 pm
Atomic radius (calc.
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1, −1
(amphoteric oxide)
Electronegativity 2.20 (Pauling scale) More

Atomic radius 25 pm
Atomic radius (calc.) 53 pm
Covalent radius 37 pm
Van der Waals radius 120 pm
Miscellaneous

Thermal conductivity (300 K) 180.
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4, 2
(mildly acidic oxide)
Electronegativity 2.55 (Pauling scale)
Ionization energies
(more) 1st: 1086.5 kJmol−1
2nd: 2352.6 kJmol−1
3rd: 4620.5 kJmol−1

Atomic radius 70 pm
Atomic radius (calc.
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2, −1
(neutral oxide)
Electronegativity 3.44 (Pauling scale)
Ionization energies
(more) 1st: 1313.9 kJmol−1
2nd: 3388.3 kJmol−1
3rd: 5300.5 kJmol−1

Atomic radius 60 pm
Atomic radius (calc.
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Identifiers
Symbol ARG2

Entrez 384
HUGO 664
OMIM 107830

RefSeq NM_001172
UniProt P78540
Other data
EC number 3.5.3.1
Locus Chr. 14 q24.1 Arginase is a manganese-containing enzyme.
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Arginine (abbreviated as Arg or R)[1] is an α-amino acid. The L -form is one of the 20 most common natural amino acids. Its codons are CGU, CGC, CGA and CGG.
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Urea is an organic compound with the chemical formula (NH2)2CO.

Urea is also known as carbamide, especially in the recommended International Nonproprietary Names (rINN) in use in Europe.
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The urea cycle (also known as the ornithine cycle) is a cycle of biochemical reactions occurring in many animals that produces urea from ammonia (NH3). This cycle was the first metabolic cycle discovered (Krebs and Kurt Henseleit, 1932).
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3, 5, 4, 2
(strongly acidic oxide)
Electronegativity 3.04 (Pauling scale)
Ionization energies
(more) 1st: 1402.3 kJmol−1
2nd: 2856 kJmol−1
3rd: 4578.1 kJmol−1

Atomic radius 65 pm
Atomic radius (calc.
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Protein biosynthesis (synthesis) is the process in which cells build proteins. The term is sometimes used to refer only to protein translation but more often it refers to a multi-step process, beginning with amino acid synthesis and transcription which are then used for translation.
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lactam (the noun is a portmanteau of the words lactone + amide) is a cyclic amide. Prefixes may indicate the ring size: β-lactam (4-membered), γ-lactam (5-membered), δ-lactam (6-membered ring).
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The enzyme ornithine decarboxylase (ODC) is a homodimer of 461 amino acids (in humans, at least).

Reaction

It catalyzes the decarboxylation of ornithine producing, as a result, diamine putrescine:

ornithine

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polyamines are organic compounds having two or more primary amino groups - such as putrescine, cadaverine, spermidine, and spermine - that are growth factors in both eucaryotic and procaryotic cells.

Cyclen is the main representative of a class of cyclic polyamines.
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Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound NH2(CH2)4NH2 (1,4-diaminobutane or butanediamine).
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E. coli

Binomial name
Escherichia coli
(Migula 1895)
Castellani and Chalmers 1919

Escherichia coli (IPA: [ˌɛ.
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Glutamic acid or glutamate (abbreviated as Glu or E; Glx or Z represents either glutamic acid or glutamine), is the protonated form of glutamate (the anion). Glutamate is one of the 20 proteinogenic amino acids.
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