Hydrolytic cleavage of pyroglutamyl-peptide bond. III. A highly selective cleavage in 70% methanesulfonic acid

Article abstract of DOI:10.1248/cpb.44.2033

A method for highly selective cleavage of pGlu-peptide linkages in 70% methanesulfonic acid (MSA) is described. When pGlu-Ala-Phe-OH, pGlu-His-Pro- OH and dog neuromedin U-8 (d-NMU-8) (1-7)-OH (pGlu-Phe-Leu-Phe-Arg-Pro-Arg- OH) were hydrolyzed in 70% MSA at 60°C for 3 h or at 25°C for 3 d, the pGlu-peptide linkage was predominantly cleaved to give H-Ala-Phe-OH, H-His- Pro-OH and H-Phe-Leu-Phe-Arg-Pro-Arg-OH, in high yields. The results indicated that pGlu-peptide linkages are highly susceptible to 70% MSA, whereas the amide bond of the pyrrolidone moiety of the pGlu residue and other internal peptide bonds are extremely resistant.

Full text of DOI:10.1248/cpb.44.2033

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