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Late‐Stage Chemoenzymatic Installation of Hydroxy‐Bearing Allyl Moiety on the Indole Ring of Tryptophan‐Containing Peptides
Author(s) -
Mupparapu Nagaraju,
Brewster Lauren,
Ostrom Katrina F.,
Elshahawi Sherif I.
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202104614
Subject(s) - indole test , moiety , tryptophan , chemistry , ring (chemistry) , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , amino acid
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.