Department of Biomedical and Pharmaceutical Sciences, Chapman University School of Pharmacy Rinker Health Science Campus, Irvine, CA 92618, USA.
Chemistry. 2022 Apr 6;28(20):e202104614. doi: 10.1002/chem.202104614. Epub 2022 Mar 10.
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.
具有反应性基团的吲哚和色氨酸化合物的晚期功能化促进了下游的多样化，并导致其生物学性质的变化。此处描述了两种带有羟基的烯丙基焦磷酸酯的合成。展示了一种化学生物酶方法，该方法使用混杂的吲哚前体转移酶酶直接在含色氨酸的肽的吲哚环上安装带有双反应性羟基的烯丙基基团。这是首例使用该反应性基团进行晚期吲哚修饰的报道。
