Biocatalytic Synthesis of α-Amino Ketones

Abstract Stereospecific generation of α-amino ketones from common α-amino acids is difficult to achieve, often employing superstoichiometric alkylating reagents and requiring multiple protecting group manipulations. In contrast, the α-oxoamine synthase protein family performs this transformation ste...

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Bibliographic Details
Published in:Synlett 2019-07, Vol.30 (11), p.1269-1274
Main Authors: Chun, Stephanie W., Narayan, Alison R. H.
Format: Article
Language:English
Subjects:
synpacts
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Summary:Abstract Stereospecific generation of α-amino ketones from common α-amino acids is difficult to achieve, often employing superstoichiometric alkylating reagents and requiring multiple protecting group manipulations. In contrast, the α-oxoamine synthase protein family performs this transformation stereospecifically in a single step without the need for protecting groups. Herein, we detail the characterization of the 8-amino-7-oxononanoate synthase (AONS) domain of the four-domain polyketide-like synthase SxtA, which natively mediates the formation of the ethyl ketone derivative of arginine. The function of each of the four domains is elucidated, leading to a revised proposal for the initiation of saxitoxin biosynthesis, a potent neurotoxin. We also demonstrate the synthetic potential of SxtA AONS, which is applied to the synthesis of a panel of novel α-amino ketones. 1 Introduction 2 Native SxtA Module Activity 3 New Reactions with SxtA AONS 4 Conclusions and Outlook
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1611755