Skip to Content
Merck
  • Enzyme architecture: the effect of replacement and deletion mutations of loop 6 on catalysis by triosephosphate isomerase.

Enzyme architecture: the effect of replacement and deletion mutations of loop 6 on catalysis by triosephosphate isomerase.

Biochemistry (2014-05-16)
Xiang Zhai, Maybelle K Go, AnnMarie C O'Donoghue, Tina L Amyes, Scott D Pegan, Yan Wang, J Patrick Loria, Andrew D Mesecar, John P Richard
ABSTRACT

Two mutations of the phosphodianion gripper loop in chicken muscle triosephosphate isomerase (cTIM) were examined: (1) the loop deletion mutant (LDM) formed by removal of residues 170-173 [Pompliano, D. L., et al. (1990) Biochemistry 29, 3186-3194] and (2) the loop 6 replacement mutant (L6RM), in which the N-terminal hinge sequence of TIM from eukaryotes, 166-PXW-168 (X = L or V), is replaced by the sequence from archaea, 166-PPE-168. The X-ray crystal structure of the L6RM shows a large displacement of the side chain of E168 from that for W168 in wild-type cTIM. Solution nuclear magnetic resonance data show that the L6RM results in significant chemical shift changes in loop 6 and surrounding regions, and that the binding of glycerol 3-phosphate (G3P) results in chemical shift changes for nuclei at the active site of the L6RM that are smaller than those of wild-type cTIM. Interactions with loop 6 of the L6RM stabilize the enediolate intermediate toward the elimination reaction catalyzed by the LDM. The LDM and L6RM result in 800000- and 23000-fold decreases, respectively, in kcat/Km for isomerization of GAP. Saturation of the LDM, but not the L6RM, by substrate and inhibitor phosphoglycolate is detected by steady-state kinetic analyses. We propose, on the basis of a comparison of X-ray crystal structures for wild-type TIM and the L6RM, that ligands bind weakly to the L6RM because a large fraction of the ligand binding energy is utilized to overcome destabilizing electrostatic interactions between the side chains of E168 and E129 that are predicted to develop in the loop-closed enzyme. Similar normalized yields of DHAP, d-DHAP, and d-GAP are formed in LDM- and L6RM-catalyzed reactions of GAP in D2O. The smaller normalized 12-13% yield of DHAP and d-DHAP observed for the mutant cTIM-catalyzed reactions compared with the 79% yield of these products for wild-type cTIM suggests that these mutations impair the transfer of a proton from O-2 to O-1 at the initial enediolate phosphate intermediate. No products are detected for the LDM-catalyzed isomerization reactions in D2O of [1-(13)C]GA and HPi, but the L6RM-catalyzed reaction in the presence of 0.020 M dianion gives a 2% yield of the isomerization product [2-(13)C,2-(2)H]GA.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Imidazole, anhydrous, free-flowing, Redi-Dri, ACS reagent, ≥99%
Sigma-Aldrich
Imidazole, ReagentPlus®, 99%, Redi-Dri, free-flowing
Sigma-Aldrich
Imidazole, for molecular biology, ≥99% (titration), free-flowing, Redi-Dri
Imidazole, European Pharmacopoeia (EP) Reference Standard
Supelco
DL-Dithiothreitol solution, 1 M in H2O
Sigma-Aldrich
DL-Dithiothreitol solution, BioUltra, for molecular biology, ~1 M in H2O
Sigma-Aldrich
Acetaldehyde diethyl acetal, 99%
Sigma-Aldrich
Imidazole, BioUltra, for molecular biology, ≥99.5% (GC)
Sigma-Aldrich
Imidazole, puriss. p.a., ≥99.5% (GC)
Sigma-Aldrich
Imidazole, BioUltra, ≥99.5% (GC)
Sigma-Aldrich
Imidazole, ReagentPlus®, 99%
Sigma-Aldrich
Deuterium chloride solution, 1.0 M in diethyl ether, 97.5 atom % D
Sigma-Aldrich
Deuterium chloride solution, 35 wt. % in D2O, ≥99 atom % D
Sigma-Aldrich
Imidazole, ACS reagent, ≥99% (titration)
Sigma-Aldrich
Imidazole, ≥99% (titration), crystalline
Sigma-Aldrich
DL-Glyceraldehyde 3-phosphate solution, 45-55 mg/mL in H2O
Sigma-Aldrich
Imidazole, for molecular biology, ≥99% (titration)
Ondansetron impurity E, European Pharmacopoeia (EP) Reference Standard
Supelco
Imidazole, Pharmaceutical Secondary Standard; Certified Reference Material
USP
Imidazole, United States Pharmacopeia (USP) Reference Standard
Sigma-Aldrich
Acetal, natural, ≥97%, FG
Sigma-Aldrich
Deuterium oxide, filtered, 99.8 atom % D
Sigma-Aldrich
Deuterium oxide, 99.9 atom % D, contains 1 % (w/w) 3-(trimethylsilyl)-1-propanesulfonic acid, sodium salt (DSS)
Sigma-Aldrich
Sodium deuteroxide solution, 30 wt. % in D2O, 99 atom % D
Sigma-Aldrich
Barium, rod, diam. ~2 cm, ≥99% trace metals basis
Sigma-Aldrich
Barium, dendritic pieces, purified by distillation, 99.9% trace metals basis
Sigma-Aldrich
Sodium deuteroxide solution, 40 wt. % in D2O, 99 atom % D
Sigma-Aldrich
Barium, pieces, 1 cm, 99% trace metals basis
Sigma-Aldrich
Deuterium oxide, 99.9 atom % D, contains 0.05 wt. % 3-(trimethylsilyl)propionic-2,2,3,3-d4 acid, sodium salt
Sigma-Aldrich
Deuterium chloride, 99 atom % D