Chemo‐Enzymatic Dynamic Kinetic Resolution of Amino Acid Thioesters

Dario Arosio, Antonio Caligiuri, Paola D’Arrigo, Giuseppe Pedrocchi‐Fantoni, Cristina Rossi, C. Saraceno, Stefano De Servi, Davide Tessaro

Advanced Synthesis & Catalysis · 2007 · 27 citations · 11 references

Concepts

Abstract

Abstract The L ‐forms of racemic‐ N‐ protected‐β,γ‐unsaturated α‐amino acid thioesters were found to be substrates for the subtilisin‐catalysed hydrolysis to the corresponding acids. The D ‐enantiomer was continuously racemised in the presence of an organic base. The combined reactions in a biphasic system allowed the deracemisation of the amino acid derivatives based on a dynamic kinetic resolution. Excellent yields and enantioselectivities were achieved.

References

11