SOLID-PHASE SYNTHESIS USING A NEW POLYACRYLIC RESIN - SYNTHESIS OF THE FRAGMENT 14-21 OF THE AMINO-ACID SEQUENCE OF HISTONE H-4

The solid-phase synthesis of the octapeptide 1 AcGly-Ala-Lys-Arg-His-Arg-Lys-ValOMe, which represents the fragment 14-21 of the amino acid sequence of the chromosomal histone H4, as well as of the structurally related nonapeptide 2 AcGly-Ala-Lys-Leu-Arg-His-Arg-Lys-ValOMe, is described using a new polyacrylic resin containing a glycolamide ester linkage (resin-NHCO-CH2-OCO-peptide) acting as a labile anchoring moiety between the resin and the peptide. After elongation of the polypeptide chain using classical protecting groups, i.e. butyloxycarbonyl for the .alpha.-NH2 function, benzyloxycarbonyl, nitro and 2,4-dinitrophenyl groups for the side-chains of Lys,Arg and His respectively, both peptides 1 and 2 were obtained in good yields and with a high purity as shown by high-pressure liquid chromatography, by amino-acid analysis by high-field proton NMR spectroscopy. This work demonstrates the ability of the newly introduced polyacrylic resin to act as a convenient support for solid-phase peptide synthesis.