Effects of chirality and substituents at carbon 3 in dihydroxyacetone-phosphate analogues on their binding to rabbit muscle aldolase.
A series of dihydroxyacetone-phosphate (DHAP) analogues has been synthesized, differing in their stereochemistry and functionality at C-3. The kinetic effects of these compounds on the enzyme aldolase (EC 4.1.2.13) have been studied and differing modes of action observed. Competitive and time dependent reversible inhibition have been shown to take place both with and without borohydride detected formation of an immonium ion.
Blonski
C
C
Groupe de Chimie Organique Biologique, URA au CNRS 470, Université Paul Sabatier, Toulouse, France.
Gefflaut
T
T
Perie
J
J
D000818:Animals; D001665:Binding Sites; D001667:Binding, Competitive; D004099:Dihydroxyacetone Phosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism* / Q000494:pharmacology; D005634:Fructose-Bisphosphate Aldolase / Q000037:antagonists & inhibitors / Q000378:metabolism*; D007700:Kinetics; D009132:Muscles / Q000201:enzymology*; D010755:Organophosphates / Q000378:metabolism / Q000494:pharmacology; D011409:Propylene Glycols / Q000378:metabolism / Q000494:pharmacology; D011817:Rabbits; D012545:Schiff Bases / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D010755:Organophosphates; D011409:Propylene Glycols; D012545:Schiff Bases; C097930:3-hydroxypropane-1-phosphate; D004099:Dihydroxyacetone Phosphate; D005634:Fructose-Bisphosphate Aldolase