Density Functional Studies on Secondary Amides: Role of Steric Factors in Cis/Trans Isomerization.

ABSTRACT: Cis/trans isomerization of amide bonds is a key step in a wide range of biological and synthetic processes. Occurring through C-N amide bond rotation, it also coincides with the activation of amides in enzymatic hydrolysis. In recently described QM studies of cis/trans isomerization in secondary amides using density functional methods, we highlighted that a peptidic prototype, such as glycylglycine methyl ester, can suitably represent the isomerization and complexities arising out of a larger molecular backbone, and can serve as the primary scaffold for model structures with different substitution patterns in order to assess and compare the steric effect of the substitution patterns. Here, we describe our theoretical assessment of such steric effects using tert-butyl as a representative bu

SUBMITTER: Thakkar BS 

PROVIDER: S-EPMC6222500 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature