Document Type
Article
Publication Date
2-17-2022
Abstract
The late-stage functionalization of indole- and tryptophan-containing compounds with reactive moieties facilitates downstream diversification and leads to changes in their biological properties. Here, the synthesis of two hydroxy-bearing allyl pyrophosphates is described. A chemoenzymatic method is demonstrated which uses a promiscuous indole prenyltransferase enzyme to install a dual reactive hydroxy-bearing allyl moiety directly on the indole ring of tryptophan-containing peptides. This is the first report of late-stage indole modifications with this reactive group.
Recommended Citation
Mupparapu N, Brewster L, Ostrom KF, Elshahawi SI. Late-stage chemoenzymatic installation of hydroxy-bearing allyl moiety on the indole ring of tryptophan-containing peptides. Chemistry. 2022. https://doi.org/10.1002/chem.202104614
Supporting Information
Copyright
The authors
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.
Included in
Amino Acids, Peptides, and Proteins Commons, Chemical and Pharmacologic Phenomena Commons, Enzymes and Coenzymes Commons, Medicinal and Pharmaceutical Chemistry Commons, Other Pharmacy and Pharmaceutical Sciences Commons
Comments
This article was originally published in Chemistry in 2022.https://doi.org/10.1002/chem.202104614