N-HYDROXY AMIDES. II. N-BENZYLOXY alpha -AMINO ACID N-HYDROXYSUCCINIMIDE ESTERS AND SYNTHESIS OF A HEXAPEPTIDE HAVING AN ALTERNATING N-HYDROXY AMIDE-AMIDE SEQUENCE.

Article abstract of DOI:10.1246/bcsj.57.2456

Acylation of a series of N-benzyloxy alpha -amino acid derivatives with N,N-phthaloyloglycine shows that the yield decreases with increasing bulkiness of the substituent even by the acyl chloride or mixed anhydride procedure, and that the use of an excess reagent or a double acylation technique is needed to attain a good yield. The low reactivity of the benzyloxyamino group enables the authors to utilize N-benzyloxy alpha -amino acid N-hydroxysuccinimide esters without N-protection in the acylation of the usual amino group. In an an attempt to lengthen the chain of an N-hydroxy peptide, a hexapeptide anilide having an N-hydroxy-DL-alanylglycyl sequence was synthesized via N-benzyloxy peptides.