L-DOPA is the best drug we have for Parkinson’s disease, but its molecular mirror image, D-DOPA, causes dangerous side effects. Making L-DOPA without also making D-DOPA is surprisingly hard and requires a specific kind of molecule to pull off. But that specific molecule must be made from a different and equally specific molecule. In this video, our host George explains how one of the winners of the 2001 Nobel Prize in Chemistry pulled it off, and why "chiral synthesis," as it's called, is really just turtles all the way down.
Sources:
- The twists and turns of chiral chemistry | Nature Chemistry
- Nature through the looking glass | symmetry magazine
- Bioinspired chiral inorganic nanomaterials | Nature Reviews Bioengineering
- Double vision | Nature Chemistry
- Why are all proteins ‘left-handed’? New theory could solve origin of life mystery | Science | AAAS
- Ketamine: A tale of two enantiomers - Luke A Jelen, Allan H Young, James M Stone, 2021
- Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers | Scientific Reports
- Chiral Drugs: An Overview - PMC
- Stereoselective Crystallization as a Basis for Single‐Enantiomer Drug Production - Bredikhin - 2017 - Chemical Engineering & Technology - Wiley Online Library
- A brief history of levodopa | Journal of Neurology
- Classics in Chemical Neuroscience: Levodopa | ACS Chemical Neuroscience
- L-DOPA - PMC
- Stereoselective Crystallization as a Basis for Single‐Enantiomer Drug Production - Bredikhin - 2017 - Chemical Engineering & Technology - Wiley Online Library
- Carbidopa And Levodopa (Oral Route) Proper Use - Mayo Clinic
- Levodopa: History and Therapeutic Applications - PMC
- Levodopa: the story so far | Nature
- Advanced Information - The Nobel Prize in Chemistry 2001
- The Nobel Prize in Chemistry 2001 - Popular information - NobelPrize.org
- Introduction to provocative questions in left–right asymmetry | Philosophical Transactions of the Royal Society B: Biological Sciences
- Cell chirality: its origin and roles in left–right asymmetric development - PMC
- Left–Right Determination: Involvement of Molecular Motor KIF3, Cilia, and Nodal Flow - PMC
- Symmetry Breaking in Biology - PMC
- Asymmetric Synthesis of Active Pharmaceutical Ingredients | Chemical Reviews
- Catalytic Asymmetric Synthesis of α-Amino Acids | Chemical Reviews
- Chemical asymmetric synthesis | Nature
- Modification of Parkinsonism — Chronic Treatment with L-Dopa | New England Journal of Medicine
- L-DOPA: From a biologically inactive amino acid to a successful therapeutic agent | Amino Acids
- LXV.—Synthesis of dl-3 : 4-dihydroxyphenylalanine - Journal of the Chemical Society, Transactions (RSC Publishing)
- New route to the preparation and configurational correlation of optically active phosphine oxides | Journal of the American Chemical Society
- Phosphororganische verbindungen optisch aktive tertiäre phosphine aus optisch aktiven quartären phosphoniumsalzen - ScienceDirect
- Conformation of Organophosphorus Compounds. II. Proton Magnetic Resonance Studies of Some Phosphites, Phosphonites, Phosphates, Phosphonates and Additional Phosphinates | Journal of the American Chemical Society
- Structural effects on the complexing ability of alkyl diphenylphosphinates with magnesium iodide - Chemical Communications (London) (RSC Publishing)
- Nucleophilic displacement reactions on organophosphorus esters by Grignard reagents. III. The reaction of alkyl diphenylphosphinates with alkyl Grignards | The Journal of Organic Chemistry
- Observing chirality and the ‘handedness’ of sugar | The Mole | RSC Education
- ‘Breakthrough’ could explain why life molecules are left- or right-handed | Science | AAAS
- Privileged Chiral Catalysts | Science
- Application of organometallic catalysis to the commercial production of L-DOPA | Journal of Chemical Education
- Stereoselective Crystallization as a Basis for Single‐Enantiomer Drug Production - Bredikhin - 2017 - Chemical Engineering & Technology - Wiley Online Library
- Stereoselective Crystallization as a Basis for Single‐Enantiomer Drug Production - Bredikhin - 2017 - Chemical Engineering & Technology - Wiley Online Library
- Monsanto | History, Products, Acquisition, & Facts
- Chirality of New Drug Approvals (2013–2022): Trends and Perspectives | Journal of Medicinal Chemistry
- Enzymatic strategies for asymmetric synthesis - RSC Chemical Biology (RSC Publishing)
- Enzymes useful for chiral compound synthesis: structural biology, directed evolution, and protein engineering for industrial use - PubMed
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