Enzymic and nonenzymic transformations of chorismic acid and related cyclohexadienes

Quantum chemical modeling of the reaction path of chorismate mutase based on the experimental substrate/product complex

“…) and is formally a Claisen rearrangement. This unimolecular reaction occurs readily both in solution and by enzyme catalysis , representing a tractable model system in many ways. In particular, the CM of Bacillus subtilis (BsCM) has been extensively studied biochemically and computationally .…”

Genetic separability of the chorismate mutase and prephenate dehydrogenase components of the Escherichia coli tyrA gene product

“…Such strains may release some prephenate into the external medium. Prephenate can be converted to phenylpyruvate (the reaction normally catalyzed by the prephenate dehydratase component of the pheA gene product) by general acid catalysis (15,16). We have previously observed that phenylpyruvate permits the growth of pheA mutants of E. coli (unpublished data), indicating that E. coli can utilize exogenous phenylpyruvate for the synthesis of phenylalanine.…”

Role ofp-Aminophenylalanine in Biosynthesis of Corynecins and Aromatic Amino Acids byCorynebacterium hydrocarboclastus

“…If 4-amino-3-enolpyruvy1cyclohexa-l, 5-dienecarboxylic acid is the precursor of p-aminobenzoic acid as proposed by Dardenne et al 14 ) and Haslam,151 transformation of this compound to PAP is considered to be a similar process as that of chorismate to tyrosine or phenylalanine where early steps are performed by enzymic and nonenzymic reactions. 16 ) In view of the data of this experiment, it seems likely that the control of Corynecin biosynthesis is exerted among the reactions following the formation of PAP, including the N-acylation, the hydroxylation at the carbon f3 to nitrogen, reduction of carboxyl group and the oxidation of aromatic amino group to nitro group.…”