Synthesis and biological activities of analogs of D-glucosyl-L-tyrosine, a humoral factor that stimulates transcription of the acyl-CoA binding protein in the pheromone gland of the Silkmoth, Bombyx mori

摘要

β-D-Glucosyl-O-L-tyrosine (1) is a humoral factor that stimulates transcription of the acyl-CoA binding protein (ACBP) in the pheromone gland of the Silkmoth, Bombyx mori. This paper describes stereoselective synthesis of five analogs that changed the sugar and/or amino acid part in 1 and their stimulatory activities on the ACBP transcription in the pheromone gland of B. mori. Among the analogs tested, β-D-galactosyl-O-L-tyrosine showed a 1/5 potency compared to the activity of 1.