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Synfacts 2025; 21(01): 51
DOI: 10.1055/a-2467-6165
Metals in Synthesis

Dehydrogenation of Apolar Amino Acids to Access Versatile Non-Canonical Amino Acids

Contributor(s):
Mark Lautens 
,
Colton E. Johnson
Gu X, Zhang Y-A, Zhang S, Wang L, Ye X, Occhialini G, Barbour J, Pentelute BL, Wendlandt AE *. Massachusetts Institute of Technology, Boston, USA
Synthesis of Non-Canonical Amino Acids Through Dehydrogenative Tailoring.

Nature 2024;
634: 352-358
DOI: 10.1038/s41586-024-07988-8
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Keywords

non-canonical amino acids - dehydrogenation - cobalt catalysis - base-metal catalysis

Significance

Wendlandt, Pentelute and co-workers report efficient access to dehydrogenated non-canonical amino acids (NCAAs) utilizing a decatungstate/cobaloxime catalyst system. These dehydrogenated residues can be easily diversified into a wide range of synthetically useful NCAAs via functionalization of the resulting alkene.


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Comment

This was inspired by the work of Sorenson (Nat. Commun. 2015, 6, 10093) which demonstrated that this dual catalytic system can be used to dehydrogenate small molecules. In this case, the initial HAA by NaDT dictates the selectivity to the γ-position of the amino acid.


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Publication History

Article published online:
20 December 2024

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