Amide Bond Cleavage: Acceleration Due to a 1,3-Diaxial Interaction with a Carboxylic Acid
The Journal of Organic Chemistry2006Vol. 72(2), pp. 654–657
Citations Over Time
Abstract
To independently assess the contribution of ground-state pseudoallylic strain to the enormous rates of amide bond cleavage in tertiary amide derivatives of Kemp's triacid, we have studied four amide derivatives of (1alpha-3alpha-5beta)-5-tert-butyl-1,3-cyclohexanedicarboxylic acid. Our results demonstrate that absent pseudoallylic strain, a 1,3-diaxial interaction of an amide with a carboxylic acid leads to only a 2400-fold increase in the rate of amide bond cleavage as compared with the rate of hydrolysis of an unactivated peptide bond.
Related Papers
- → Fast Amide Bond Cleavage Assisted by a Secondary Amino and a Carboxyl Group—A Model for yet Unknown Peptidases?(2019)13 cited
- → 4-[(4-Chlorophenyl)carbamoyl]butanoic Acid(2021)3 cited
- [Study on the amide of 2-chlorobornan-4-carboxylic acid].(1977)
- [Synthesis of virostatically acting N[adamantyl-(1)]-carbonic acid amides].(1975)
- → Lignin Linkages Cleavage Beginning with C α O–H/ArO–H or C α –OH Bond Heterolysis(2022)