Levodopa (Molecule of the Month for October 2016)
L-DOPA
Levodopa or L-DOPA is an intermediate in dopamine biosynthesis. Clinically, levodopa is used in the management of Parkinson's disease.
Levodopa is used as a prodrug to increase dopamine levels for the treatment of Parkinson's disease, since it is able to cross the blood-brain barrier whereas dopamine itself cannot. Once levodopa has entered the central nervous system (CNS), it is metabolized to dopamine by aromatic-L-amino-acid decarboxylase. However, conversion to dopamine also occurs in the peripheral tissues, causing adverse effects and decreasing the available dopamine to the CNS, so it is standard practice to co-administer a peripheral DOPA decarboxylase inhibitor.
In work that earned him a Nobel Prize in 2000, Swedish scientist Arvid Carlsson first showed in the 1950s that administering levodopa to animals with Parkinsonian symptoms would cause a reduction of the symptoms. The 2001 Nobel Prize in Chemistry was also related to L-DOPA: the Nobel Committee awarded one-fourth of the prize to William S. Knowles for his work on chirally catalysed hydrogenation reactions, the most noted example of which was used for the synthesis of L-DOPA.
Formal Chemical Name (IUPAC)
(S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
References
click on the picture of Levodopa above to interact
with the 3D model of the
Levodopa structure
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C9H11NO4
Update by Karl Harrison
(Molecule of the Month for
October 2016
)
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