Pentapeptide Nanoreactor as a Platform for Halogenations, Diels-Alder Reaction, and Morita-Baylis-Hillman Reaction.

ABSTRACT: A pentapeptide nanoreactor has been designed and synthesized as a platform to carry out the traditional organic reactions such as bromination, iodination, cycloaddition, and condensation reactions. The pentapeptide Boc-Phe-Phe-Aib-Phe-Phe-OMe with a supramolecular helical structure and π-rich channel provides nanoconfinements and thus facilitates the organic reactions. Bromination and iodination of aniline take place without any halogen carrier (Lewis acid) in the pentapeptide platform. Iodination produced p-iodoaniline only. The Diels-Alder reaction between furan and maleic anhydride increased 2-fold in the pentapeptide platform and the Morita-Baylis-Hillman reaction of benzaldehyde and ethyl acrylate in methanol enhanced 1.5-fold.

SUBMITTER: Debnath M 

PROVIDER: S-EPMC6714524 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature