title: New hydroxyl protecting groups of a safety-catch type removable by reductive acidolysis.
abstract: New hydroxyl protecting groups of a safety-catch type, i.e., 4-methylsulfinylbenzyl-oxycarbonyl (Msz) group for Tyr and 4-methylsulfinylbenzyl (Msob) ether for Thr, have been developed. O-Msz and O-Msob groups are stable under both acidic and basic conditions and can be removed by a one-pot reaction involving reductive acidolysis using tetrachlorosilane-trifluoroacetic acid (TFA)-scavengers. Using these new protecting groups, a 17 residue-peptide, gamma-endorphin, was successfully synthesized by the efficient solid phase method.
authors.affiliation: Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Kiso
authors.forename: S
authors.initials: S
authors.lastname: Tanaka
authors.forename: T
authors.initials: T
authors.lastname: Kimura
authors.forename: H
authors.initials: H
authors.lastname: Itoh
authors.forename: K
authors.initials: K
authors.lastname: Akaji
mesh_terms: D000595:Amino Acid Sequence; D001593:Benzyl Compounds / Q000138:chemical synthesis*; D004723:Endorphins / Q000138:chemical synthesis*; D006868:Hydrolysis; D008969:Molecular Sequence Data; D013440:Sulfides / Q000138:chemical synthesis*; D018823:gamma-Endorphin
chemical_list: D001593:Benzyl Compounds; D004723:Endorphins; D013440:Sulfides; D018823:gamma-Endorphin