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Combined approach of backbone amide linking and on-resin n-methylation for the synthesis of bioactive and metabolically stable peptides

Wesche, Frank and Adihou, Hélène and Kaiser, Astrid and Wurglics, Mario and Schubert-Zsilavecz, Manfred and Kaiser, Marcel and Bode, Helge B.. (2018) Combined approach of backbone amide linking and on-resin n-methylation for the synthesis of bioactive and metabolically stable peptides. Journal of medicinal chemistry, 61 (9). pp. 3930-3938.

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Official URL: https://edoc.unibas.ch/64899/

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Abstract

Rhabdopeptides are a large class of nonribosomal peptides from the bacteria Xenorhabdus and Photorhabdus with low micromolar activity against different protozoa, which are the causative agents of several tropical diseases. The development of a facile and flexible synthesis combining backbone amide linking with on-resin peralkylation for the synthesis of permethylated rhabdopeptides is described. This strategy allows the fast generation of permethylated naturally occurring and artificial rhabdopeptides for a structure-activity study. Furthermore, in vitro experiments revealed their superior properties regarding their stability and passive membrane diffusion.
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 (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:0022-2623
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:04 Jul 2018 08:59
Deposited On:04 Jul 2018 08:59

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