Sulfonylcarbamates as Amino Protecting Groups in Peptide Chemistry
- 1 January 1976
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 6 (1) , 17-20
- https://doi.org/10.1080/00397917608062127
Abstract
In a search for new peptide coupling agents N-acetyl-L-phenylalanine and methyl L-alaninate were treated with p-tosylisocyanate in the hope of obtaining the model racemization peptide methyl N-acetyl-L-phenylalanyl-L-alaninate and benzenesulfonamide.1 Instead, the reaction gave in moderate yield alanyl tosylhydantoin, identified by an independent synthesis and spectral data. This result suggested that the treatment of an amino acid (1) with p-tosyliso-cyanate (2) would yield the corresponding p-tosyl-aminocarbonyl derivative (3) or Tac-Amino acid.Keywords
This publication has 3 references indexed in Scilit:
- Zur Verwendung des Tosylaminocarbonyl‐Restes als Amino‐Schutzgruppe in der PeptidchemieHelvetica Chimica Acta, 1975
- Amino-acids and peptides. Part XXVIII. Determination of racemization in peptide synthesis by nuclear magnetic resonance spectroscopyJournal of the Chemical Society, Perkin Transactions 1, 1972
- N-[(4-Tolysulfonyl)carbamoyl]amino AcidsJournal of Medicinal Chemistry, 1966