The structure of a glyoxalase I inhibitor and its chemical reactivity with SH-compounds.
The structure of a glyoxalase I inhibitor (I), isolated from a cultured broth of Streptomyces griseosporeus, was found to be 2-crotonyloxymethyl-4,5,6-trihydroxy-cyclohex-2-enone by chemical studies. Stereochemistry and absolute configuration were determined to be 4R, 5R and 6R by X-ray crystallographic analysis of a bromine-containing crystalline derivative. The crotonyloxy group of I shows a surprising proclivity to be displaced by SH-compounds. This property is shown to be the basis for its biological activity.
D000903:Antibiotics, Antineoplastic / Q000302:isolation & purification / Q000494:pharmacology; D002087:Butyrates; D055598:Chemical Phenomena; D002621:Chemistry; D003437:Crotonates / Q000302:isolation & purification; D005978:Glutathione; D007791:Lactoylglutathione Lyase / Q000037:antagonists & inhibitors*; D008190:Lyases / Q000037:antagonists & inhibitors*; D008623:Mercaptoethanol; D013302:Streptomyces / Q000032:analysis; D013329:Structure-Activity Relationship; D013438:Sulfhydryl Compounds; D014961:X-Ray Diffraction
D000903:Antibiotics, Antineoplastic; D002087:Butyrates; D003437:Crotonates; D013438:Sulfhydryl Compounds; D008623:Mercaptoethanol; D008190:Lyases; D007791:Lactoylglutathione Lyase; D005978:Glutathione