FORMATION AND SYNTHESIS OF 3‘‐t‐BUTYLTYROSINE
- 1 October 1979
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 14 (4) , 344-346
- https://doi.org/10.1111/j.1399-3011.1979.tb01942.x
Abstract
During acidolysis by trifluoroacetic acid of the tert-butyl (But) protecting group from Z[benzyloxycarbonyl]-Tyr(But) or from Ser(But) in the presence of tyrosine, C-tert-butylation occurred in the aromatic nucleus in Z-Tyr or tyrosine, respectively, to an extent of 0.5-1.0%. CF3COOBut formed during the acidolysis slowly C-tert-butylates tyrosine. Tyr(3''But) is formed. The synthesis of Tyr(3''But) .cntdot. HCl is described.Keywords
This publication has 9 references indexed in Scilit:
- REMOVAL OF t‐BUTYL AND t‐BUTOXYCARBONYL PROTECTING GROUPS WITH TRIFLUOROACETIC ACIDInternational Journal of Peptide and Protein Research, 1978
- SIDE REACTIONS IN PEPTIDE SYNTHESIS. VI.International Journal of Peptide and Protein Research, 1978
- Tyrosine protecting groups: minimization of rearrangement to 3-alkyltyrosine during acidolysisJournal of the American Chemical Society, 1978
- SIDE REACTIONS IN PEPTIDE-SYNTHESIS .6. RE-EXAMINATION OF BENZYL GROUP IN PROTECTION OF SIDE-CHAINS OF TYROSINE AND ASPARTIC-ACID1978
- Acid stability of several benzylic protecting groups used in solid-phase peptide synthesis. Rearrangement of O-benzyltyrosine to 3-benzyltyrosineJournal of the American Chemical Society, 1973
- Alkyl exchange reactions in trifluoroacetic acid. t-Butyl trifluoroacetate, an efficient alkylation agent for aromatic compoundsJournal of the Chemical Society, Perkin Transactions 1, 1973
- Butylation of the tryptophan indole ring: a side reaction during the removal of t-butyloxycarbonyl and t-butyl protecting groups in peptide synthesisJournal of the Chemical Society D: Chemical Communications, 1970
- Exchange of Carbon-Bound Hydrogen Atoms ortho to the Hydroxyl Group in TyrosineScience, 1965
- Chromatography of Amino Acids on Sulfonated Polystyrene Resins. An Improved SystemAnalytical Chemistry, 1958