Ontology highlight
ABSTRACT:
SUBMITTER: Zou Y
PROVIDER: S-EPMC9328771 | biostudies-literature | 2020 Nov
REPOSITORIES: biostudies-literature
Zou Yike Y Yang Song S Sanders Jacob N JN Li Wei W Yu Peiyuan P Wang Hongbo H Tang Zhijun Z Liu Wen W Houk K N KN
Journal of the American Chemical Society 20201114 47
We studied the mechanisms of activation and stereoselectivity of a monofunctional Diels-Alderase (PyrI4)-catalyzed intramolecular Diels-Alder reaction that leads to formation of the key spiro-tetramate moiety in the biosynthesis of the pyrroindomycin family of natural products. Key activation effects of PyrI4 include acid catalysis and an induced-fit mechanism that cooperate with the unique "lid" feature of PyrI4 to stabilize the Diels-Alder transition state. PyrI4 enhances the intrinsic Diels-A ...[more]