91061-47-1

Upstream product

• 116130-27-9 1-((S)-2-Carboxy-1-methyl-2-oxo-ethyl)-4-hydroxy-cyclohexa-2,5-dienecarboxylic acid 
• 151-50-8 potassium cyanide 

Downstream Products

• 68258-25-3 3-Phenyl-1,2-butanediol 
• 28645-07-0 (S)-methyl 2-phenylpropanoate 
• 7782-24-3 (S)-2-Phenylpropionic acid 
• 91828-70-5 (S)-2-Hydroxy-3-phenyl-butyric acid methyl ester 

Relevant academic research and scientific papers

Uncatalyzed and Chorismate Mutase Catalyzed Claisen Rearrangement of (Z)-9-Methylchorismic Acid

A synthesis of (-)- and (+/-)-(Z)-9-methylchorismic acid (3) is reported.The half-life for the uncatalyzed Claisen rearrangement of (+/-)-3 in H2O (pH 7.5, 30 deg C) is 5.7 h.Chorismate analogue (-)-3 was a modest substrate for chorismate mutase (chorismate mutase-prephenate dehydrogenase from E. coli): Km = 4.0 mM, kcat./kuncat. = 4.2*104.It was established that the enzyme-catalyzed Claisen rearrangement of (-)-3 proceeds through a chairlike transition state in similar fashion to the chorismate mutase catalyzed rearrangement of (-)-chorismic acid (1).