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Enantioselective Transaminations by Dendrimeric Enzyme Mimics
Ronald Breslow1, Sujun Wei, Craig Kenesky
1Department of Chemistry, Columbia University, New York NY 10027.
Tetrahedron
|July 4, 2008
Summary
Chiral pyridoxamine dendrimers demonstrate remote induction of enantioselectivity in transamination reactions. Computer models support dendrimer chain folding, explaining this chiral influence.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Computational Chemistry
Background:
- Dendrimers are highly branched macromolecules with unique properties.
- Chiral recognition is crucial in asymmetric synthesis.
- Pyridoxamine derivatives have shown promise in catalysis.
Purpose of the Study:
- To construct pyridoxamine-cored dendrimers with chiral capping groups.
- To investigate the ability of these dendrimers to induce enantioselectivity in transamination reactions.
- To explore the structural basis for remote chiral induction using computational modeling.
Main Methods:
- Synthesis of pyridoxamine-cored dendrimers with chiral amino caps.
- Asymmetric transamination reactions of ketoacids to form phenylalanine and alanine.
- Computational modeling to predict dendrimer conformation and chiral induction mechanisms.
Main Results:
- Successful construction of novel chiral dendrimers.
- Demonstrated enantioselectivity in the formation of phenylalanine and alanine.
- Computer models indicated significant folding of dendrimer chains towards the core.
- Chiral caps remotely influenced the stereochemical outcome of the reactions.
Conclusions:
- Pyridoxamine-cored dendrimers with chiral caps can induce enantioselectivity.
- The observed enantioselectivity is attributed to the conformational folding of dendrimer chains.
- This study provides evidence for remote chiral induction in dendrimeric systems.
