Preparation of dehydropeptides
AssigneeResearch Corporation
InventorCharles H. Stammer
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Abstract
A preparation of azlactones represented by the formula ##STR1## wherein R is a substituted or unsubstituted alkyl, aryl or nitrogen containing heterocyclic group, and R.sup.1 is an N-blocked amino acid residue or peptide chain, and stereoisomers thereof, by oxidizing the corresponding saturated azlactone with a benzoquinone oxidizing agent in the presence of a base is disclosed. The unsaturated azlactones, some of which are novel, can be converted to dehydro peptides, which are useful as intermediates for preparing novel biologically active compounds, or themselves have biological activity.
Claims3
A method of stabilizing peptides to enzymatic degradation comprising introducing a dehydrophenylalanine group into the peptide chain so as to produce a dehydropeptide selected from the group consisting of:
- aspartyl-dehydrophenylalanine methyl ester;
- tyrosyl-D-alanyl-glycyl-dehydrophenylalanine methionine amide;
- arginyl-prolyl-prolyl-glycyl-dehydrophenylalanylseryl-prolyl-phenylalanyl-a rginine;
- N-carbobenzoxy-prolyl-dehydrophenylalanylhistidyl-leucine, and its stereoisomers;
- leucyl-dehydrophenylalanyl-valyl-phenylalanine methyl ester;
- --N-t-butoxy carboxyl-D-alanyl-glycyldehydrophenylalanyl-methionine amide;
- and
- tyrosyl-D-alanyl-glycyl-dehydrophenylalanylmethionine amide acetate.
Dependencies are inferred from the claim text.