bc0c00256_si_001.pdf (1.9 MB)
Chemoselective Methionine Bioconjugation: Site-Selective Fluorine-18 Labeling of Proteins and Peptides
journal contribution
posted on 2020-08-06, 11:36 authored by Daniel Lin, Michael Wallace, Alban J. Allentoff, David J. Donnelly, Erin Gomes, Kim Voronin, Sharon Gong, Richard Y.-C. Huang, Ho Kim, Janet Caceres-Cortes, Samuel BonacorsiChemoselective
methionine bioconjugation with alkyne-bearing oxaziridine
and alkyne-bearing iodonium salts was investigated as a new platform
for site-selective radiolabeling of proteins and peptides with fluorine-18.
Alkyne-bearing sulfimide conjugates, resulting from oxaziridine modification,
underwent copper-assisted alkyne–azide cycloaddition (CuAAC)
with an 18F-labeled PEGylated azide to afford 18F-labeled triazoles in excellent radiochemical yields. Diazoester
sulfonium salt bioconjugates, formed from alkyne-bearing 2-diazoiodonium
salts, gave low yields of 18F-labeled triazoles and were
shown to be unstable to CuAAC conditions. Photolytic removal of the
diazo group, however, afforded the trialkylsulfonium salt which smoothly
underwent CuAAC with the 18F-labeled PEGylated azide to
afford high radiochemical yields of the desired 18F-labeled
click product. Overall, the results establish the viability of chemoselective
methionine bioconjugation as a method for preparing site-selective 18F-labeled PET radioligands.
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radiochemical yieldsfluorine -18. Alkyne-bearing sulfim...CuAACalkyne-bearing iodonium salts18 F-labeled click productPeptides Chemoselective methionine ...Chemoselective Methionine Bioconjug...Site-Selective Fluorine -18chemoselective methionine bioconjug...alkyne-bearing 2- diazoiodonium salts18 F-labeled triazoles18 F-labeled PEGylated azideDiazoester sulfonium salt bioconjugatessite-selective 18 F-labeled PET rad...
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