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.
beta-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, beta-d-galactosyl-O-l-tyrosine showed a 1/5 potency compared to the activity of 1.
Takahashi
Shunya
S
RIKEN (The Institute of Physical and Chemical Research), Wako-shi, Saitama 351-0198, Japan. shunyat@riken.go.jp
Hasumi
Keiko
K
Ohnishi
Atsushi
A
Koshino
Hiroyuki
H
Matsumoto
Shogo
S
D000818:Animals; D001681:Biological Assay; D012831:Bombyx / Q000737:chemistry / Q000187:drug effects* / Q000378:metabolism*; D026261:Diazepam Binding Inhibitor / Q000378:metabolism*; D005260:Female; D005786:Gene Expression Regulation / Q000187:drug effects*; D008968:Molecular Conformation; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D011679:Pupa / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
C517082:D-glucosyl-l-tyrosine; D026261:Diazepam Binding Inhibitor; D009005:Monosaccharides; D014443:Tyrosine