SYNTHESIS OF ISOSTERIC METHYLENE-OXY PSEUDOPEPTIDE ANALOGUES AS NOVEL AMIDE BOND SURROGATE UNITS

Article abstract of DOI:10.1016/S0040-4020(01)96090-9

The syntheses of several fully protected dipeptide isosteres which incorporate a methylene-oxy bond replacing the amide bond are described.The novel methylene-oxy modification offers a polar, flexible, proteolytically resistant peptide bond surrogate which can be easily incorporated into biologically active peptides.The standard geometries of the trans-amide, methylene-oxy and methylene-thio units are compared, showing a very close geometrical resemblance of the ψ2-O> unit to the amide bond.