In:
Angewandte Chemie, Wiley, Vol. 132, No. 8 ( 2020-02-17), p. 3067-3071
Abstract:
Herein, we report an engineered enzyme that can monooxygenate unprotected tryptophan into the corresponding 3a‐hydroxyhexahydropyrrolo[2,3‐b]indole‐2‐carboxylic acid (HPIC) in a single, scalable step with excellent turnover number and diastereoselectivity. Taking advantage of directed evolution, we analyzed the stepwise oxygen‐insertion mechanism of tryptophan 2,3‐dioxygenases, and transformed tryptophan 2,3‐dioxygenase from Xanthomonas campestris into a monooxygenase for oxidative cyclization of tryptophans. It was revealed that residue F51 is vital in determining the product ratio of HPIC to N ′‐formylkynurenine. Our reactions and purification procedures use no organic solvents, resulting in an eco‐friendly method to prepare HPICs for further applications.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.201911825
Language:
English
Publisher:
Wiley
Publication Date:
2020
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514305-6
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505872-7
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1479266-7
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