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Kinetics and mechanism of the decomposition of N,N-dihalopeptides

โœ Scribed by William D. Stanbro; Michael J. Lenkevich

Publisher
John Wiley and Sons
Year
1985
Tongue
English
Weight
547 KB
Volume
17
Category
Article
ISSN
0538-8066

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โœฆ Synopsis

The tripeptide alanylalanylalanine reacts with either HOCl or HOBr to form a N, Ndihalopeptide. These compounds decompose to the N-halo-N'-(a-iminoket0)peptides plus halide ion. The rate constants for these reactions in 0.4-M NaCl were determined to be (PH 6.7) k4 = 1.06 x 1015e 18,400'RT min-' (PH 6.6) (71: k -1.52 101je-19.600/RT 4 -Br:

where the activation energies are in cal/mol. The N-halo-N '-(a-iminoketobpeptides slowly decompose either by a two-step hydrolysis reaction to form ammonia, halide ion, and an N-(a-acylketo)peptide, or by direct decomposition to a nitrile, an isocyanopeptide, and a halide ion.

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