Regiodivergent biocatalytic hydroxylation of L-Glutamine facilitated by characterization of Non-Heme dioxygenases from Non-Ribosomal peptide biosyntheses

TETRAHEDRON

卷:90

Article

Renata, Hans¹  Shimizu, Emily¹  Zwick, Christian R.¹ 

[1] Scripps Res Inst, Dept Chem, 130 Scripps Way, Jupiter, FL 33458 USA

关键词: Amino acid hydroxylase;    Nonheme dioxygenase;    Nonribosomal peptide;    C-H oxidation;   

DOI  :  10.1016/j.tet.2021.132190

来源: Elsevier

【 摘 要 】

We report the functional characterization of two iron- and alpha-ketoglutarate-dependent dioxygenases that are capable of hydroxylating free-standing glutamine at its C3 and C4 position respectively. In particular, the C4 hydroxylase, Q4Ox, catalyzes the reaction with approximately 4300 total turnover numbers, facilitating synthesis of a solid-phase compatible building block and stereochemical elucidation at the C4 position of the hydroxylated product. This work will enable the development of novel synthetic strategies to prepare useful glutamine derivatives and stimulate further discoveries of new amino acid hydroxylases with distinct substrate specificities. (C) 2021 Elsevier Ltd. All rights reserved.

【 授权许可】

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