Synfacts 2009(1): 0093-0093  
DOI: 10.1055/s-0028-1087426
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Formal Enzymatic Reductive Amination with Ammonia

Contributor(s):Benjamin List, Lars Ratjen
D. Koszelewski, I. Levandera, D. Clay, G. M. Guebitz, D. Rozzell, W. Kroutil*
University of Graz and University of Technology, Graz, Austria; Codexis, Inc., Redwood City, USA
Formal Asymmetric Biocatalytic Reductive Amination
Angew. Chem. Int. Ed.  2008,  47:  9337-9340  
Further Information

Publication History

Publication Date:
18 December 2008 (online)


Significance

The authors report a biocatalytic reductive amination of ketones. The transformation is catalyzed by a combination of three different enzymes, a transaminase, an alanine dehydrogenase and a formate dehydrogenase. Under consumption of alanine to pyruvate, the products are formed with high yields and outstanding enantioselectivities. The recycling of alanine and the co-factor NAD(P)H is effected by ammonium ­formate in two independent enzymatic operations, producing water and CO2 as only by-products.

Comment

Reductive amination is one of the most powerful and versatile methods for the ­preparation of amines from simple carbonyl ­compounds. The reported mild and efficient procedure shows the high potential of enzymes. Further investigations can give rise to more sophisticated and complex molecules involving biocatalysis. Beside several metal- and organocatalytic methods, this procedure represents a complementary and green approach towards ­nitrogen-containing molecules.