Peptidic thiacyclols. Synthesis and structural studies
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1153-1157
- https://doi.org/10.1039/p19840001153
Abstract
Deprotection with tri-n-butylphosphine in aqueous medium of 2-t-butyldithiopropionyl-L-phenylalanyl-L-proline p-nitrophenyl ester gives stable thiacyclols. These compounds are isomeric with nine-membered peptidic thiolactones and possess the same stereochemistry at the phenylalanine and proline chiral centres as found in natural oxacyclols (ergot alkaloids). Spectroscopic properties and an X-ray crystallographic analysis are reported. Crystals of the thiacyclol (14) are orthorhombic with a= 16.462(7), b= 15.763(7), c= 6.487(4)Å, Z= 4, space group P212121.This publication has 1 reference indexed in Scilit:
- Flexibility of the pyrrolidine ring in proline peptidesBiopolymers, 1977