オキシム樹脂固相合成およびセグメント縮合法によるペプチド・タンパク質の合成

抄録

In 1980, E. T. Kaiser developed a 4-nitrobenzophenone oxime resin which is useful for the preparation of protected peptides by solid-phase synthesis followed by cleavage from the resin. Standing on this merit, he has also proposed “segment synthesis and condensation” strategy for the synthesis of long chain polypeptides. In past 10 years, several improvements have been achieved by various his successors for the practical application of his strategy for the synthesis of proteins. To increase the applicability, the introduction of various starting amino acids, coupling reagents and protecting groups were examined and selected. Now Kaiser's oxime resin finds special advantages in the synthesis of artificial proteins by de novo design, in which peptides are hybridized with various non-peptidyl compounds such as porphyrins and organic metal complexes. In addition, extreme usefulness was discovered for the convenient synthesis of cyclic peptides by solid-phase synthesis and cyclization-cleavage with the oxime resin. Since increasing contribution of Kaiser's oxime resin is expected for the variously designed syntheses of polypeptide-related compounds, we review here the recent progress in the peptide synthesis based on the oxime resin to provide a manual for a number of young synthetic organic chemists.