Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water.

摘要: We report the functionalization of cysteine residues with lipophilic alkynes bearing silyl groups and alkyl chains using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co-solvent or removal oxygen, either at 37 °C room temperature. transformation led a significant increase peptide lipophilicity worked for aromatic thiols, homocysteine, peptides containing 4 18 amino acids. His -Cys-Ubiquitin was also alkynylated under physiological conditions. Under acidic conditions, thioalkynes converted into thioesters, which could be cleaved presence hydroxylamine.