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.
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
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.
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