New hydroxyl protecting groups of a safety-catch type removable by reductive acidolysis. |
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Authors: | Y Kiso S Tanaka T Kimura H Itoh K Akaji |
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Affiliation: | Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan. |
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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. |
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