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Literature summary for 2.4.1.1 extracted from

  • Cheng, K.; Liu, J.; Liu, X.; Li, H.; Sun, H.; Xie, J.
    Synthesis of glucoconjugates of oleanolic acid as inhibitors of glycogen phosphorylase (2009), Carbohydr. Res., 344, 841-850.
    View publication on PubMed
Search for more literature for 2.4.1.1

Inhibitors

Inhibitors Comment Organism Structure
3-O-[1-(methyl 6-deoxy-alpha-D-glucopyranosid-6-yl)-1H-1,2,3-triazol-4-yl]methyl 3b-hydroxyolean-12-en-28-oate inhibitor is predicted to bind at the T-state allosteric site exclusively. The binding position of the oleanolic acid moiety occupies the same location as the T-state allosteric site of asiatic acid in the crystal structure. The newly attached sugar moiety shields the carboxyl group of oleanolic acid from forming the salt bridge with Arg310, and consequently reverses the orientation of the oleanolic acid as well as propelled the sugar moiety to extend more deeply into the alloteric dimer interface. As a result, a new hydrogen-bonding network forms between the sugar hydroxyls and the carboxyl of Asp227 plus the guanidino of Arg193, respectively, enhancing their contribution to the stability of the complex Oryctolagus cuniculus
6-[4-(methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranosiduronylmethyl)-1H-1,2,3-triazol-1-yl]hexyl 3beta-hydroxyolean-12-en-28-oate
-
 Oryctolagus cuniculus
benzyl 3-O-propargyl-3beta-hydroxyolean-12-en-28-oate
-
 Oryctolagus cuniculus

Organism

Organism UniProt Comment Textmining
Oryctolagus cuniculus P00489 glycogen phosphorylase a
-

Source Tissue

Source Tissue Comment Organism Textmining
muscle
-
 Oryctolagus cuniculus
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
starch + phosphate
-
 Oryctolagus cuniculus starch + D-glucose 1-phosphate
-
 ?

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00114
-
 pH 6.0, 37°C Oryctolagus cuniculus 3-O-[1-(methyl 6-deoxy-alpha-D-glucopyranosid-6-yl)-1H-1,2,3-triazol-4-yl]methyl 3b-hydroxyolean-12-en-28-oate
0.0116
-
 pH 6.0, 37°C Oryctolagus cuniculus 6-[4-(methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranosiduronylmethyl)-1H-1,2,3-triazol-1-yl]hexyl 3beta-hydroxyolean-12-en-28-oate
0.0265
-
 pH 6.0, 37°C Oryctolagus cuniculus benzyl 3-O-propargyl-3beta-hydroxyolean-12-en-28-oate