[70a] Preparation of prephenic acid (cas 126-49-8)☆

Add time:09/10/2019    Source:sciencedirect.com

Publisher SummaryThis chapter describes the preparation of prephenic acid. In Escherichia coli and in Salmonella, chorismic acid is converted to phenylpyruvate and to 4-hydroxyphenylpyruvate, respectively, by bifunctional enzymes that catalyze as a first step, the rearrangement of chorismate to prephenate. This method uses a tyrosine auxotroph of S. typhimurium, which has chorismate mutase but no prephenate dehydrogenase activity to accumulate prephenate under resting conditions. The cells are suspended in a medium that is devoid of tyrosine but contains tryptophan and phenylalanine to inhibit anthranilate synthase and prephenate dehydratase, respectively. Under resting conditions, the tyrosine auxotrophs of Salmonella produce less acid than phenylalanine auxotrophs. Certain phenylalanine and tyrosine auxotrophs are partially blocked. They are able to carry out only the first reaction in the sequence and may, therefore, excrete prephenate. The advantages of the method considered include a shorter incubation time, smaller volume of medium to process, and accumulation under nonsterile conditions.

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