Mishra, Abhaya KumarTessier, RomainHari, Durga PrasadWaser, Jerome2021-07-172021-07-172021-07-172021-07-1210.1002/anie.202106458https://infoscience.epfl.ch/handle/20.500.14299/179974WOS:000671878200001We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co-solvent or removal of oxygen, either at 37 degrees C or room temperature. The transformation led to a significant increase of peptide lipophilicity and worked for aromatic thiols, homocysteine, cysteine, and peptides containing 4 to 18 amino acids. His(6)-Cys-Ubiquitin was also alkynylated under physiological conditions. Under acidic conditions, the thioalkynes were converted into thioesters, which could be cleaved in the presence of hydroxylamine.Chemistry, MultidisciplinaryChemistryamphiphilic reagentshypervalent iodinelipidationlipopeptideubiquitincysteinelipophilicityacidoxidationalkynylationacylationproteinsbehaviorprobestext::journal::journal article::research article