ArticleNature2017
Stereodivergent synthesis with a programmable molecular machine.
Article in Nature, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 47 papers.
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Who cites it
47 citing papers in PubMed, 177 citations in OpenAlex.
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- The Influence of Strain on the Rotation of an Artificial Molecular Motor.Angewandte Chemie (International ed. in English) · 2022Article
- Controlling catalyst activity, chemoselectivity and stereoselectivity with the mechanical bond.Nature reviews. Chemistry · 2022Review
- A Chiral Molecular Cage Comprising Diethynylallenes and N-Heterotriangulenes for Enantioselective Recognition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Complex molecular logic gates from simple molecules.RSC advances · 2021Article
- Pressure-driven, solvation-directed planar chirality switching of cyclophano-pillar[5]arenes (molecular universal joints).Chemical science · 2021Article
- Site-to-site peptide transport on a molecular platform using a small-molecule robotic arm.Chemical science · 2020Article
- Configurational and Constitutional Dynamics of Enamine Molecular Switches.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Study on the Influence of Chirality in the Threading of Calix[6]arene Hosts with Dialkylammonium Axles.Molecules (Basel, Switzerland) · 2020Article
- Cyclization of interlocked fumaramides into β-lactams: experimental and computational mechanistic assessment of the key intercomponent proton transfer and the stereocontrolling active pocket.Chemical science · 2020Article
- Engineering control circuits for molecular robots using synthetic biology.APL materials · 2020Article
- A molecular assembler that produces polymers.Nature communications · 2020Article
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Authors and funding
6 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
It has been convincingly argued that molecular machines that manipulate individual atoms, or highly reactive clusters of atoms, with Ångström precision are unlikely to be realized. However, biological molecular machines routinely position rather less reactive substrates in order to direct chemical reaction sequences, from sequence-specific synthesis by the ribosome to polyketide synthases, where tethered molecules are passed from active site to active site in multi-enzyme complexes. Artificial molecular machines have been developed for tasks that include sequence-specific oligomer synthesis and the switching of product chirality, a photo-responsive host molecule has been described that is able to mechanically twist a bound molecular guest, and molecular fragments have been selectively transported in either direction between sites on a molecular platform through a ratchet mechanism. Here we detail an artificial molecular machine that moves a substrate between different activating sites to achieve different product outcomes from chemical synthesis. This molecular robot can be programmed to stereoselectively produce, in a sequential one-pot operation, an excess of any one of four possible diastereoisomers from the addition of a thiol and an alkene to an α,β-unsaturated aldehyde in a tandem reaction process. The stereodivergent synthesis includes diastereoisomers that cannot be selectively synthesized through conventional iminium-enamine organocatalysis. We anticipate that future generations of programmable molecular machines may have significant roles in chemical synthesis and molecular manufacturing.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.