Ontology highlight
ABSTRACT:
SUBMITTER: Lam YH
PROVIDER: S-EPMC3325492 | biostudies-literature | 2012 Apr
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20120329 14
Quantum mechanical calculations reveal the origin of diastereo- and enantioselectivities of aldol reactions between aldehydes catalyzed by histidine, and differences between related reactions catalyzed by proline. A stereochemical model that explains both the sense and the high levels of the experimentally observed stereoselectivity is proposed. The computations suggest that both the imidazolium and the carboxylic acid functionalities of histidine are viable hydrogen-bond donors that can stabili ...[more]