Cyclol formation from tripeptides containing β-alanine
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 1311-1316
- https://doi.org/10.1039/p19820001311
Abstract
Attempts to synthesize stable tetrahedral intermediates (cyclols) from β-alanine containing precursors are described. Cyclization of N-(N-benzyloxycarbonyl-β-alanyl)-Phe-Pro-ONp gave N-(N-benzyloxycarbonyl-β-alanyl)cyclo-(Phe-D-Pro). Cyclization of N-(N-benzyloxycarbonyl-Ala)-βAla-Pro-ONp and of N[N-(R)-(α-hydroxyisovaleryl)-βAla]-Pro-ONp afforded the corresponding anhydrocyclols. The first example of an oxa-cyclol related to a ten-membered cyclodepsitripeptide was synthesized by acylating cyclo-(βAla-Pro) with α-benzyloxypropionyl chloride followed by hydrogenolytic removal of the O-benzyl protecting group.This publication has 3 references indexed in Scilit:
- Peptidic cyclols. Synthesis, and crystal and molecular structure of a tricyclic thia-cyclolJournal of the Chemical Society, Perkin Transactions 1, 1980
- Activation of the amide group by acylationTetrahedron, 1965
- The stereospecific cyclolization of N-(α-hydroxyacyl)-phenylalanyl-proline lactamsTetrahedron, 1963