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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.


This article was originally published in Chemistry in 2022.

chem202104614-sup-0001-misc_information.pdf (8847 kB)
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This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.



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