NDLI: Investigation of a general base mechanism for ester hydrolysis in C–C hydrolase enzymes of the α/β-hydrolase superfamily: a novel mechanism for the serine catalytic triad

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Molecular springs, muscles, rheostats, and precessing gyroscopes: from review to preview

Self-assembled multivalent carbohydrate ligands

Recent approaches towards the asymmetric synthesis of α,α-disubstituted α-amino acids

An unusual stereoselectivity in the anomeric substitution with carbamates promoted by HNTf₂

Efficient ruthenium and copper cocatalzyed five-component coupling to form dipropargyl amines under mild conditions in water

Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium

Chemo-enzymatic synthesis and biological evaluation of photolabile nicotinic acid adenine dinuclotide phosphate (NAADP⁺)

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Selective intercalation of six ligand molecules in a self-assembled triple helix

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Ring expansion reactions of 4-amino-1,1-dioxo-[1,2,3,5]-thiatriazoles

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The aminolysis of N-aroyl β-lactams occurs by a concerted mechanism

Synthesis and evaluation of caged Garcinia xanthones

On the enantioselective olefin epoxidation by doubly bridged biphenyl azepine derivatives – mixed tropos/atropos chiral biaryls

Investigation of a general base mechanism for ester hydrolysis in C–C hydrolase enzymes of the α/β-hydrolase superfamily: a novel mechanism for the serine catalytic triad

Chemoenzymatic synthesis of trans-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-dihydrodiol isomers

Structural and theoretical investigation of 2-iminoimidazolines – carbene analogues of iminophosphoranes

Synthetic ansamycins prepared by a ring-expanding Claisen rearrangement. Synthesis and biological evaluation of ring and conformational analogues of the Hsp90 molecular chaperone inhibitor geldanamycin

Density functional study of the conformations and intramolecular proton transfer in thiohydroxamic acids

Tetraurea calix[4]arenes with sulfur functions: synthesis, dimerization to capsules, and self-assembly on gold

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Investigation of a general base mechanism for ester hydrolysis in C–C hydrolase enzymes of the α/β-hydrolase superfamily: a novel mechanism for the serine catalytic triad

Content Provider	Royal Society of Chemistry (RSC)
Author	Bugg, Timothy D. H. Li, Jian-Jun
Copyright Year	2007
Abstract	Previous mechanistic and crystallographic studies on two C–C hydrolase enzymes, Escherichia coli MhpC and Burkholderia xenovorans BphD, support a general base mechanism for C–C hydrolytic cleavage, rather than the nucleophilic mechanism expected for a serine hydrolase. The role of the active site serine residue could be to form a hydrogen bond with a gem-diolate intermediate, or to protonate such an intermediate. Hydrolase BphD is able to catalyse the hydrolysis of p-nitrophenyl benzoate ester substrates, which has enabled an investigation of these mechanisms using a Hammett analysis, and comparative studies upon five serine esterases and lipases from the α/β-hydrolase family. A reaction parameter (ρ) value of +0.98 was measured for BphD-catalysed ester hydrolysis, implying a build-up of negative charge in the transition state, consistent with a general base mechanism. Values of +0.31–0.61 were measured for other serine esterases and lipases, for the same series of esterase substrates. Pre-steady state kinetic studies of ester hydrolysis, using p-nitrophenyl acetate as the substrate, revealed a single step kinetic mechanism for BphD-catalysed ester hydrolysis, with no burst kinetics. A general base mechanism for BphD-catalysed ester hydrolysis is proposed, in which Ser-112 stabilises an oxyanion intermediate through hydrogen bonding, and assists the rotation of this oxyanion intermediate via proton transfer, a novel reaction mechanism for the serine catalytic triad.
Starting Page	507
Ending Page	513
Page Count	7
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	5
Issue Number	3
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/b615605c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Benzoic acid Escherichia Hydrolase Escherichia coli Active site Serine Oxyanion Serine hydrolase Hydrolysis Ester Esterase Catalytic triad Proton Reaction mechanism Hammett equation Burkholderia Hydrogen bond
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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