Synthesis of an actinomycin-related peptide lactone from the corresponding cyclic pentapeptide by NO-acyl shift
- 12 January 2009
- journal article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 34 (3) , 196-199
- https://doi.org/10.1111/j.1399-3011.1989.tb00230.x
Abstract
The N,O-acyl shift was investigated as a method for the synthesis of an O-peptide or peptide lactone from a linear or cyclic peptide respectively. Protected derivatives of glycyl-L-threonine could be converted to O-peptides by the action of HCl/dioxane at room temperature and N-acylated under conditions which precluded a reverse O,N-acyl shift. For effecting N,O-acyl shift in cyclo(Thr-D-Val-Pro-Sar-MeAla) this reagent was unsatisfactory and p-toluenesulfonic acid in dioxane at 80 degrees was used instead. The resulting crystalline peptide lactone p-toluenesulfonate salt was N-acylated with 3-benzyloxy-4-methyl-2-nitrobenzoyl chloride to afford a known intermediate in the synthesis of 5,5'-MeAla actinomycin D. This approach constitutes a novel synthetic route to actinomycins and potentially to other peptide lactone antibiotics.Keywords
This publication has 12 references indexed in Scilit:
- The remarkable sensitivity to acid‐catalyzed peptolysis of peptide chains (endopeptolysis) having a succession of three N‐alkylated amino acid residuesInternational Journal of Peptide and Protein Research, 1988
- Conformation and dimerization of actinomycin-related peptide lactones in solution and in the solid stateJournal of the American Chemical Society, 1985
- Synthesis of an actinomycin-related peptide, cyclo-(Thr-D-Val-Pro-Sar-MeAla), and conformational studies by nuclear magnetic resonance and x-ray crystallographyJournal of the American Chemical Society, 1982
- Rapid chromatographic technique for preparative separations with moderate resolutionThe Journal of Organic Chemistry, 1978
- Insulin methyl ester. Specific cleavage of a peptide chain resulting from a nitrogen to oxygen acyl shift at a threonine residueBiochemistry, 1970
- Formic Acid Saturated with Boron Trifluoride as a Reagent for Acyl Rearrangement of ProteinsNippon kagaku zassi, 1970
- An Approach to the Specific Cleavage of Peptide Bonds. I. The Acyl Migration in Dipeptides Containing Hydroxyamino Acids in Anhydrous Hydrogen FluorideJournal of the American Chemical Society, 1962
- The Determination of S equence Containing Hydroxyamino Acid in Clupeine and Salmine Molecules by Making Use of N→O Peptidyl Shift.Nippon kagaku zassi, 1961
- Acyl N → O Shift in Poly-DL-SerineScience, 1960
- A search for specific chemical methods for fission of peptide bonds. 1. The N-acyl to O-acyl transformation in the degradation of silk fibroinBiochemical Journal, 1952