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Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
Author(s) -
Mishra Abhaya Kumar,
Tessier Romain,
Hari Durga Prasad,
Waser Jerome
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202106458
Subject(s) - chemistry , hydroxylamine , reagent , amphiphile , lipophilicity , cysteine , peptide , alkyl , organic chemistry , solvent , silylation , combinatorial chemistry , amino acid , iodine , biochemistry , enzyme , copolymer , catalysis , polymer
Abstract We 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 °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.