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- W36542972 abstract "This chapter discusses nonenzymatic cleavage of histidyl peptide bonds. Histidyl residues (I) have a double bond in the γ-δ position relative to the carbonyl group of the peptide bond. When histidyl peptides are treated with 3 moles of N-bromosuccinimide (NBS) in 50% aqueous acetic acid at room temperature, they are cleaved in 18–28% yield. However, if the reaction mixture is heated for 1 h at 100°, the yields rise to 50–65%. If the reaction with NBS is performed in a buffer of pyridine–acetic acid–water, almost no cleavage occurs at room temperature; however, on heating, 55–65% cleavage is obtained. In the pyridine acetate buffer, the water competes with the peptide bond for the bromonium ion initially formed and brings about rupture of the imidazole ring. As a result of this, α-ketoaldehyde, ammonia, and formamide are formed." @default.
- W36542972 created "2016-06-24" @default.
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- W36542972 date "1966-01-01" @default.
- W36542972 modified "2023-09-24" @default.
- W36542972 title "NON-ENZYMATIC CLEAVAGE OF HISTIDYL PEPTIDE BONDS**This investigation was supported by grants A-3171 and AM-5098 from the National Institutes of Health, United States Public Health Service." @default.
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- W36542972 doi "https://doi.org/10.1016/b978-1-4831-9851-4.50029-2" @default.
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