Synthesis of fluorine substituted oligosaccharide analogues of monoglucosylated glycan chain, a proposed ligand of lectin-chaperone calreticulin and calnexin.
As a part of a exploring the N-glycan-mediated glycoprotein quality control in endoplasmic reticulum, 2-fluorinated derivative Glcalpha1 --> 3Man(F) 1, Glcalpha1 --> 3Man(F)alpha1 --> 2Man2, and Glcalpha1 --> 3Man(F)alpha1 --> 2Manalpha1 --> 2Man 3 were synthesized in a concise manner. These oligosaccharides were subjected to binding studies with calreticulin by using isothermal titration calorimetry. It was revealed that disaccharide 1 was a poor ligand, while tri- (2) and tetrasaccharide (3) had observable affinity.
Ito
Yukishige
Y
RIKEN, The Institute of Physical and Chemical Research, 2-1 Hirosawa, Wako-shi, Saitama, 351-0198 Japan. yukito@postman.riken.go.jp
Hagihara
Shinya
S
Arai
Midori A
MA
Matsuo
Ichiro
I
Takatani
Maki
M
D037281:Calnexin / Q000737:chemistry / Q000378:metabolism*; D002151:Calorimetry; D037282:Calreticulin / Q000737:chemistry / Q000378:metabolism*; D002240:Carbohydrate Sequence; D005461:Fluorine / Q000737:chemistry; D006801:Humans; D037102:Lectins / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D018832:Molecular Chaperones / Q000737:chemistry / Q000378:metabolism*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D011993:Recombinant Fusion Proteins / Q000737:chemistry / Q000378:metabolism
D037282:Calreticulin; D037102:Lectins; D008024:Ligands; D018832:Molecular Chaperones; D009844:Oligosaccharides; D011993:Recombinant Fusion Proteins; D037281:Calnexin; D005461:Fluorine