Abstract
The conversion of readily available monosaccharides to high-value amino alcohols using a key biocatalytic step is an attractive strategy for the preparation of these chiral synthons. Here, we report a previously undescribed example of the direct amination of monosaccharides, which exist predominantly in their cyclic form at equilibrium, using amine transaminase biocatalysts, providing access to a panel of amino alcohols in moderate to high conversion and isolated yield. A recently developed high-throughput colorimetric screen, employing o-xylylenediamine, was initially used to identify amine transaminase enzymes displaying this activity towards cyclic sugars and reactions were successfully scaled-up using isopropylamine.
Highlights
The development of efficient biocatalytic routes for the synthesis of optically purechemicals and pharmaceuticals that are difficult to access using more traditional synthetic methodology remains an important challenge and has inspired the concept of biocatalytic retrosynthesis.[1]
The only report of amine transaminases (ATAs)-mediated conversion of simple sugars to amino alcohols have been with the tetroses, D-erythrose and L-erythrulose (scheme 1 (i)),[6] which do not readily form cyclic structures, and this transformation has not been reported for monosaccharides that cyclize to form hemiacetals
Biocatalysis has been successfully employed for the synthesis of valuable amino alcohols starting from simple building blocks by designing multi-enzyme cascades.6b,8 there is enormous scope for the development of a one-step strategy via direct amination from simple and accessable monosaccharides (scheme 1 (iii))
Summary
The development of efficient biocatalytic routes for the synthesis of optically pure (agro)chemicals and pharmaceuticals that are difficult to access using more traditional synthetic methodology remains an important challenge and has inspired the concept of biocatalytic retrosynthesis.[1]. Biocatalysis has been successfully employed for the synthesis of valuable amino alcohols starting from simple building blocks by designing multi-enzyme cascades.6b,8 there is enormous scope for the development of a one-step strategy via direct amination from simple and accessable monosaccharides (scheme 1 (iii)). The strategy, which exploits transaminases, allows access to a range of chiral omega-amino alcohols on a preparative-scale, starting from the corresponding aldoses.
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