540770-50-1Relevant articles and documents
De novo Biosynthesis of “Non-Natural” Thaxtomin Phytotoxins
Winn, Michael,Francis, Daniel,Micklefield, Jason
supporting information, p. 6830 - 6833 (2018/06/04)
Thaxtomins are diketopiperazine phytotoxins produced by Streptomyces scabies and other actinobacterial plant pathogens that inhibit cellulose biosynthesis in plants. Due to their potent bioactivity and novel mode of action there has been considerable interest in developing thaxtomins as herbicides for crop protection. To address the need for more stable derivatives, we have developed a new approach for structural diversification of thaxtomins. Genes encoding the thaxtomin NRPS from S. scabies, along with genes encoding a promiscuous tryptophan synthase (TrpS) from Salmonella typhimurium, were assembled in a heterologous host Streptomyces albus. Upon feeding indole derivatives to the engineered S. albus strain, tryptophan intermediates with alternative substituents are biosynthesized and incorporated by the NRPS to deliver a series of thaxtomins with different functionalities in place of the nitro group. The approach described herein, demonstrates how genes from different pathways and different bacterial origins can be combined in a heterologous host to create a de novo biosynthetic pathway to “non-natural” product target compounds.
A convenient one-step synthesis of l-aminotryptophans and improved synthesis of 5-fluorotryptophan
Winn, Michael,Roy, Abhijeet Deb,Grueschow, Sabine,Parameswaran, Raj S.,Goss, Rebecca J.M.
body text, p. 4508 - 4510 (2009/04/08)
A one-pot biotransformation for the generation of a series of l-aminotryptophans using a readily prepared protein extract containing tryptophan synthase is reported. The extract exhibits remarkable stability upon freeze-drying, and may be stored and used for long periods after its preparation without significant loss of activity.
