Abstract
Biotransformation of benzene and derivatives has been used to accumulate meta-ring fission products of several catechols, including catechol, 3- and 4- methylcatechols, and 3- (trifluoromethyl) catechol. Dilute solutions of these yellow highly absorbing products were used to examine reaction conditions that affect their facile cyclizations with nitrogen nucleophiles, principally NH3. The effects of NH4+/NH3 concentration, pH and temperature on the non-enzymic cyclizations of 2-hydroxymuconic semialdehyde to 2-picolinate and its substituted derivatives have been characterised. As expected, the enzymic product from 3-(trifluoromethyl) catechol cyclised 20 times more slowly than that from 3-methylcatechol under identical reaction conditions. Most of the biological and chemical transformations were studied in very dilute solutions for the convenience of optical absorbance measurements. Because of the known sensitivity of the spectral shifts and extinction coefficients to minor changes in pH between 4 and 8 bo...
Published Version
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