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Title

Combining aldolases and transaminases for the synthesis of 2‑amino-4-hydroxybutanoic acid

AuthorsHernández Sánchez, Karel ; Bujons, Jordi; Joglar, Jesús; Charnock, Simon J.; Domínguez de María, Pablo; Fessner, Wolf Dieter; Clapés Saborit, Pere
KeywordsAldolases
Biocatalysis
Green chemistry
Substrate cycling
Transaminases
Issue DateFeb-2017
PublisherAmerican Chemical Society
CitationACS Catalysis 7(3): 1707–1711(2017)
AbstractAmino acids are of paramount importance as chiral building blocks of life, for drug development in modern medicinal chemistry, and for the manufacture of industrial products. In this work, the stereoselective synthesis of (S)- and (R)-2-amino-4-hydroxybutanoic acid was accomplished using a systems biocatalysis approach comprising a biocatalytic one-pot cyclic cascade by coupling of an aldol reaction with an ensuing stereoselective transamination. A class II pyruvate aldolase from E. coli, expressed as a soluble fusion protein, in tandem with either an S- or R-selective, pyridoxal phosphate dependent transaminase was used as a catalyst to realize the conversion, with formaldehyde and alanine being the sole starting materials. Interestingly, the class II pyruvate aldolase was found to tolerate formaldehyde concentrations of up to 1.4 M. The cascade system was found to reach product concentrations for (S)- or (R)-2-amino-4-hydroxybutanoic acid of at least 0.4 M, rendering yields between 86% and >95%, respectively, productivities of >80 g L–1 d–1, and ee values of >99%.
Publisher version (URL)https://doi.org/10.1021/acscatal.6b03181
URIhttp://hdl.handle.net/10261/149131
DOI10.1021/acscatal.6b03181
E-ISSN2155-5435
Appears in Collections:(IQAC) Artículos
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