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- W2921207105 abstract "Engineered myoglobins were recently shown to be effective catalysts for abiological carbene and nitrene transfer reactions. Here, we investigated the impact of substituting the conserved heme-coordinating histidine residue with both proteinogenic (Cys, Ser, Tyr, Asp) and non-proteinogenic Lewis basic amino acids (3-(3'-pyridyl)-alanine, p-aminophenylalanine, and β-(3-thienyl)-alanine), on the reactivity of this metalloprotein toward these abiotic transformations. These studies showed that mutation of the proximal histidine residue with both natural and non-natural amino acids result in stable myoglobin variants that can function as both carbene and nitrene transferases. In addition, substitution of the proximal histidine with an aspartate residue led to a myoglobin-based catalyst capable of promoting stereoselective olefin cyclopropanation under nonreducing conditions. Overall, these studies demonstrate that proximal ligand substitution provides a promising strategy to tune the reactivity of myoglobin-based carbene and nitrene transfer catalysts and provide a first, proof-of-principle demonstration of the viability of pyridine-, thiophene-, and aniline-based unnatural amino acids for metalloprotein engineering." @default.
- W2921207105 created "2019-03-22" @default.
- W2921207105 creator A5009221427 @default.
- W2921207105 creator A5070780837 @default.
- W2921207105 date "2019-04-01" @default.
- W2921207105 modified "2023-10-01" @default.
- W2921207105 title "Effect of proximal ligand substitutions on the carbene and nitrene transferase activity of myoglobin" @default.
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- W2921207105 doi "https://doi.org/10.1016/j.tet.2019.03.009" @default.
- W2921207105 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/6534480" @default.
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