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Enzymatic amide bond formation: synthesis of aminooxo-acids through a Mycobacterium smegmatis acyltransferase†
Michael S. Christodoulou,Martina Letizia Contente,Sabrina Dallavalle,Andrea Pinto
Green Chemistry Pub Date : 05/25/2022 00:00:00 , DOI:10.1039/D2GC00655C
Abstract

A highly-productive strategy based on the use of an acyltransferase from Mycobacterium smegmatis (MsAcT), for the preparation of aminooxo-acids in water was developed. 1 M-scale biotransformations were carried out with excellent yields (68–94%) and rapid reactions (0.5–5 h) starting from anilines and a range of different anhydrides. The high substrate-to-catalyst ratio (Msubstrate/Mcatalyst: 25 000), enzymatic stability (one month without any activity loss), and excellent protein purification yields (130 mg from 2 g of wet cell paste) made this process a green and cost-efficient approach, which was successfully applied for the preparation of a key intermediate of SAHA synthesis.

Graphical abstract: Enzymatic amide bond formation: synthesis of aminooxo-acids through a Mycobacterium smegmatis acyltransferase
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