Synthesis of C-Protected 2,2-Dideutero β³-Amino Acids

Abstract

A simple three-step procedure for the preparation of C-protected 2,2-²H-β³-amino acids has been developed starting from the natural α-amino acids. Our synthetic path is based on the homologation reaction of α-amino acids through the formation of dideuterated alcohol intermediates obtained by heavy isotope reduction (NaBD₄) of the carboxylic function.

Key words

β³-amino acids - deuterated amino acids - isotopically labeled compounds

References

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11

Unpublished results.

12

β-Amino acids can be subdivided into β³, β², and β^2,3 amino acids, depending upon the position of the side chain(s) on the aminoalkanoic acid skeleton.

16

Ph₃P-iodine complex showed the same reactivity of the polymer bound/iodine complex towards all the tested amino acids.