New hydroxyl protecting groups of a safety-catch type removable by reductive acidolysis.
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.
Kiso
Y
Y
Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan.
Tanaka
S
S
Kimura
T
T
Itoh
H
H
Akaji
K
K
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
D001593:Benzyl Compounds; D004723:Endorphins; D013440:Sulfides; D018823:gamma-Endorphin