L-DOPA

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L-DOPA
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Molar mass 197.19 g/mol

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<templatestyles src="smallcaps/styles.css"/>l-DOPA, also known as <templatestyles src="smallcaps/styles.css"/>l-3,4-dihydroxyphenylalanine and used medically as levodopa, is made and used as part of the normal biology of some plants[1] and animals, including humans. Humans, as well as a portion of the other animals that utilize <templatestyles src="smallcaps/styles.css"/>l-DOPA, make it via biosynthesis from the amino acid <templatestyles src="smallcaps/styles.css"/>l-tyrosine.

<templatestyles src="smallcaps/styles.css"/>l-DOPA is the precursor to the neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline), which are collectively known as catecholamines. Furthermore, <templatestyles src="smallcaps/styles.css"/>l-DOPA itself mediates neurotrophic factor release by the brain and central nervous system.[2][3] In some plant families (of the order Caryophyllales), <templatestyles src="smallcaps/styles.css"/>l-DOPA is the central precursor of a biosynthetic pathway that produces a class of pigments called betalains.[4]

<templatestyles src="smallcaps/styles.css"/>l-DOPA can be manufactured and in its pure form is sold as a drug with the INNTooltip International Nonproprietary Name levodopa. As a drug, it is used in the treatment of Parkinson's disease and dopamine-responsive dystonia, as well as restless leg syndrome.[5]

<templatestyles src="smallcaps/styles.css"/>l-DOPA has a counterpart with opposite chirality, <templatestyles src="smallcaps/styles.css"/>d-DOPA. As is true for many molecules, the human body produces only one of these isomers (the <templatestyles src="smallcaps/styles.css"/>l-DOPA form). The enantiomeric purity of <templatestyles src="smallcaps/styles.css"/>l-DOPA may be analyzed by determination of the optical rotation or by chiral thin-layer chromatography.[6]

Biological role

Template:Phenylalanine biosynthesis <templatestyles src="smallcaps/styles.css"/>l-DOPA is produced from the amino acid <templatestyles src="smallcaps/styles.css"/>l-tyrosine by the enzyme tyrosine hydroxylase. <templatestyles src="smallcaps/styles.css"/>l-DOPA can act as an <templatestyles src="smallcaps/styles.css"/>l-tyrosine mimetic and be incorporated into proteins by mammalian cells in place of <templatestyles src="smallcaps/styles.css"/>l-tyrosine, generating protease-resistant and aggregate-prone proteins in vitro and may contribute to neurotoxicity with chronic <templatestyles src="smallcaps/styles.css"/>l-DOPA administration.[7] It is also the precursor for the monoamine or catecholamine neurotransmitters dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline). Dopamine is formed by the decarboxylation of <templatestyles src="smallcaps/styles.css"/>l-DOPA by aromatic <templatestyles src="smallcaps/styles.css"/>l-amino acid decarboxylase (AADC).

<templatestyles src="smallcaps/styles.css"/>l-DOPA can be directly metabolized by catechol-O-methyl transferase to 3-O-methyldopa, and then further to vanillactic acid. This metabolic pathway is nonexistent in the healthy body, but becomes important after peripheral <templatestyles src="smallcaps/styles.css"/>l-DOPA administration in patients with Parkinson's disease or in the rare cases of patients with AADC enzyme deficiency.[8]

<templatestyles src="smallcaps/styles.css"/>l-Phenylalanine, <templatestyles src="smallcaps/styles.css"/>l-tyrosine, and <templatestyles src="smallcaps/styles.css"/>l-DOPA are all precursors to the biological pigment melanin. The enzyme tyrosinase catalyzes the oxidation of <templatestyles src="smallcaps/styles.css"/>l-DOPA to the reactive intermediate dopaquinone, which reacts further, eventually leading to melanin oligomers. In addition, tyrosinase can convert tyrosine directly to <templatestyles src="smallcaps/styles.css"/>l-DOPA in the presence of a reducing agent such as ascorbic acid.[9]

History

<templatestyles src="smallcaps/styles.css"/>l-DOPA was first isolated from the seeds of the Vicia faba (broad bean) plant in 1913 by Swiss biochemist Markus Guggenheim.[10]

The 2001 Nobel Prize in Chemistry was also related to <templatestyles src="smallcaps/styles.css"/>l-DOPA: the Nobel Committee awarded one-quarter 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 <templatestyles src="smallcaps/styles.css"/>l-DOPA.[11][12][13]

File:L-dopaSyn.svg
Synthesis of <templatestyles src="smallcaps/styles.css"/>l-DOPA via hydrogenation with C2-symmetric diphosphine.

Other organisms

Marine adhesion

<templatestyles src="smallcaps/styles.css"/>l-DOPA is a key compound in the formation of marine adhesive proteins, such as those found in mussels.[14][15] It is believed to be responsible for the water-resistance and rapid curing abilities of these proteins. <templatestyles src="smallcaps/styles.css"/>l-DOPA may also be used to prevent surfaces from fouling by bonding antifouling polymers to a susceptible substrate.[16] The versatile chemistry of <templatestyles src="smallcaps/styles.css"/>l-DOPA can be exploited in nanotechnology.[17] For example, DOPA-containing self-assembling peptides were found to form functional nanostructures, adhesives and gels.[18][19][20][21]

Plants and in the environment

In plants, L-DOPA functions as an allelochemical which inhibits the growth of certain species, and is produced and secreted by a few legume species such as the broad bean Vicia faba and the velvet bean Mucuna pruriens.[22] Its effect is strongly dependent on the pH and the reactivity of iron in the soil.[23] L-DOPA can also be found in cephalopod ink.[24]

Use as a medication and supplement

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L-DOPA is used medically under the name levodopa in the treatment of Parkinson's disease and certain other medical conditions. It is usually used in combination with a peripherally selective aromatic L-amino acid decarboxylase (AAAD) inhibitor such as carbidopa or benserazide. These agents increase the strength and duration of levodopa. Combination formulations include levodopa/carbidopa and levodopa/benserazide, as well as levodopa/carbidopa/entacapone.

L-DOPA is found in high amounts in Mucuna pruriens (velvet bean) and is available and used over-the-counter as a supplement.

References

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