Highly selective cleavage of pyroglutamyl-peptide bond in concentrated hydrochloric acid.
Highly selective cleavage reaction of pGlu-peptide bond is described. Two model peptides, pGlu-X-Ala-Phe-OH (X = Ile and Ser), and dog neuromedin U-8 (d-NMU-8) (1-7)-OH (pGlu-Phe-Leu-Phe-Arg-Pro-Arg-OH) were hydrolyzed in concentrated HCl at 0 degree C for from 6 days to 6 weeks to give the predominant cleavage products of pGlu-X linkage of pGlu-X-Ala-Phe-OH and the pGlu-Phe linkage of d-NMU-8 (1-7)-OH, respectively. The ring-opening reaction of the pyrrolidone moiety of the pGlu residue occurred to a considerably lesser extent.
Hashimoto
T
T
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.
Saito
S
S
Ohki
K
K
Sakura
N
N
D000595:Amino Acid Sequence; D000818:Animals; D004285:Dogs; D006851:Hydrochloric Acid; D006868:Hydrolysis; D007700:Kinetics; D008969:Molecular Sequence Data; D010455:Peptides / Q000737:chemistry*; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry*
D010455:Peptides; D006851:Hydrochloric Acid; D011761:Pyrrolidonecarboxylic Acid