Synthesis of new Cα-tetrasubstituted α-amino acids
2009
Synthesis of New Cα-Tetrasubstituted α-Amino Acids
publication
Evidence: moderate
Author Information
Author(s): Grauer Andreas A, König Burkhard, Clayden Jonathan
Primary Institution: Institute for Organic Chemistry, University of Regensburg
Hypothesis
Can Cα-tetrasubstituted tetrahydrofuran α-amino acids be synthesized from aliphatic aldehydes?
Conclusion
Cα-tetrasubstituted tetrahydrofuran α-amino acids can be obtained from aliphatic aldehydes in low to moderate yields.
Supporting Evidence
- Cα-tetrasubstituted α-amino acids are important for stabilizing peptide structures.
- The study shows that these amino acids can be synthesized from aliphatic aldehydes.
- The diastereoselectivity of the reaction varies with the steric demand of the aldehyde.
Takeaway
Scientists found a way to make special amino acids from certain types of chemicals called aldehydes, which can help create stronger proteins.
Methodology
The synthesis involved an aldol-type reaction between a sulfonium salt and aliphatic aldehydes under basic conditions.
Limitations
The scope of the reported reaction is limited to selected aliphatic aldehydes.
Digital Object Identifier (DOI)
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