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Structure and biosynthesis of isatropolones, bioactive amine-scavenging fluorescent natural products from streptomyces Go66

Cai, Xiaofeng and Shi, Yi-Ming and Pöhlmann, Nicole and Revermann, Ole and Bahner, Isabel and Pidot, Sacha J. and Wesche, Frank and Lackner, Helmut and Büchel, Claudia and Kaiser, Marcel and Richter, Christian and Schwalbe, Harald and Stinear, Timothy P. and Zeeck, Axel and Bode, Helge B.. (2017) Structure and biosynthesis of isatropolones, bioactive amine-scavenging fluorescent natural products from streptomyces Go66. Angewandte Chemie International Edition, 56 (18). pp. 4945-4949.

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Official URL: http://edoc.unibas.ch/55119/

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Abstract

The natural products isatropolone A-C (1-3) were reisolated from Streptomyces Gö66, with 1 and 3 showing potent activity against Leishmania donovani. They contain a rare tropolone ring derived from a type II polyketide biosynthesis pathway. Their biosynthesis was elucidated by labeling experiments, analysis of the biosynthesis gene cluster, its partial heterologous expression, and structural characterization of various intermediates. Owing to their 1,5-diketone moiety, they can react with ammonia, amines, lysine, and lysine-containing peptides and proteins, which results in the formation of a covalent bond and subsequent pyridine ring formation. Their fluorescence properties change upon amine binding, enabling the simple visualization of reacted amines including proteins.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel
Item Type:Article, refereed
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:06 Jun 2017 12:10
Deposited On:06 Jun 2017 12:10

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