Phosphinyl- and Phosphinothioylamino Acids and Peptides. IV. Further Examples of Use of the Diphenylphosphinothioyl Group for the Protection of Amino Acids
- 1 May 1979
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 52 (5), 1431-1436
- https://doi.org/10.1246/bcsj.52.1431
Abstract
The preparation and purification of diphenylphosphinothioyl(Ppt)-amino acids were studied. The side-chain functional groups of tyrosine and cysteine were found to react also with diphenylphosphinothioyl chloride to form O-Ppt and S-Ppt derivatives. Acidic reagents for the removal of N-Ppt group were examined by using N,O-bis-Ppt-tyrosine ethyl ester (III) as the most difficult model, HCl in HCO2H–CH2Cl2 being found to be most preferable. The O- and S-Ppt bonds were stable during the course of acidic treatments, but could be removed by alkaline hydrolysis. An application of Ppt-amino acids to the solid phase peptide synthesis is given.Keywords
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