The use of 6-(difluoromethyl)indole to study the activation of indole by tryptophan synthase

Add time:08/22/2019    Source:sciencedirect.com

6-(difluoromethyl)indole (cas 127956-27-8) has been characterized and developed as a probe for the turnover of indole by the bifunctional enzyme, tryptophan synthase (α2β2). The neutral form of the indolyl species undergoes a slow and spontaneous hydrolysis to produce 6-formylindole with a rate constant (k1) of 0.0089 ± 0.0001 min−1. The overall rate is independent of pH in the range of 3.5–10.5. Above pH 10.5, the observed rate increases are due to the high reactivity of the anionic form of the indole; deprotonation at N-1 accelerates hydrolysis by 104-fold (k2, 97 ± 2 min−1). The magnitude of this effect provides a technique for detecting the formation or stabilization of the anionic form of indole. 6-(Difluoromethyl)indole is recognized and processed by the β subunit of tryptophan synthase. Selective inactivation of the β subunit prevents enzymatic processing of 6-(difluoromethyl)indole. Chromatographic isolation and mass spectral analysis has identified 6-(difluoromethyl)tryptophan as the sole turnover product of the indolyl substrate. The lack of enzyme-promoted dehalogenation does not exclude the formation of an indole anion during turnover but rather the data suggest that rapid carbon-carbon bond formation (>5300 min−1) prevents the accumulation of this anion.

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