l-DOPA, also known as l-3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants and animals, including humans. Humans, as well as a portion of the other animals that utilize l-DOPA, make it via biosynthesis from the amino acid l-tyrosine.
l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, l-DOPA itself mediates neurotrophic factor release by the brain and CNS. In some plant families (of the order Caryophyllales), l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains.
l-DOPA can be manufactured and in its pure form is sold as a drug with the INNTooltip International Nonproprietary Name levodopa. Trade names include Sinemet, Pharmacopa, Atamet, and Stalevo. As a drug, it is used in the treatment of Parkinson's disease and dopamine-responsive dystonia, as well as restless leg syndrome.
l-DOPA has a counterpart with opposite chirality, d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the l-DOPA form). The enantiomeric purity of l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography. |
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InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10) |
ZDXPYRJPNDTMRX-UHFFFAOYSA-N |
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Daphnia magna
(NCBI:txid35525)
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See:
PubMed
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Arabidopsis thaliana
(NCBI:txid3702)
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See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
PubMed
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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fundamental metabolite
Any metabolite produced by all living cells.
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View more via ChEBI Ontology
2,5-diamino-5-oxopentanoic acid
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IUPAC
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2-amino-4-carbamoylbutanoic acid
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JCBN
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2-Aminoglutaramic acid
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KEGG COMPOUND
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glutamic acid γ-amide
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ChEBI
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Glutamin
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ChEBI
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Glutamine
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KEGG COMPOUND
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Glutaminsäure-5-amid
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ChEBI
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Hgln
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IUPAC
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1723795
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Reaxys Registry Number
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Reaxys
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27318
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Gmelin Registry Number
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Gmelin
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585-21-7
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CAS Registry Number
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ChemIDplus
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6899-04-3
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CAS Registry Number
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ChemIDplus
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