Anthranilate synthase steric course

Fig. 7.4. Steric course of the anthranilic synthase reaction (adapted with permission from Asano et al., copyright 1985 American Chemical Society).

Having chorismic acid available with a stereospecific label in the side chain methylene group we then proceeded to determine the steric course of the anthranilate synthase reaction. The pyruvate generated in the reaction in the presence of H2O (Fig. 19) was oxidized to acetate and analyzed for its chirality. An F value of 44.5 (19% e.e. indicated that the protonation had occurred on the face. This stereochemistry is probably of no mechanistic significance, but it contrasts with that seen in virtually all the reactions in which a proton or other electrophile is added at the methylene carbon of PEP. 

Fig. 19. Steric course of the anthranilate synthase reaction. Reprinted from Reference 37 with permission of the American Chemical Society.

KOWAL, H.G. FLOSS. 1985. Steric course of the reactions catalyzed by 5-enolpyruvylshikimate-3-phosphate synthase, chorismate mutase and anthranilate synthase. J. Amer. Chem. Soc. 107, 4314-4320. 

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See also in sourсe #XX -- [ ]

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