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• W1858684328 endingPage "540" @default.
• W1858684328 startingPage "531" @default.
• W1858684328 abstract "When lactose was incubated with G794A-β-galactosidase (a variant with a closed active site loop that binds transition state analogs well) an allolactose was trapped with its Gal moiety in a (4)H3 conformation, similar to the oxocarbenium ion-like conformation expected of the transition state. The numerous interactions formed between the (4)H3 structure and β-galactosidase indicate that this structure is representative of the transition state. This conformation is also very similar to that of d-galactono-1,5-lactone, a good transition state analog. Evidence indicates that substrates take up the (4)H3 conformation during migration from the shallow to the deep mode. Steric forces utilizing His418 and other residues are important for positioning the O1 leaving group into a quasi-axial position. An electrostatic interaction between the O5 of the distorted Gal and Tyr503 as well as C-H-π bonds with Trp568 are also significant. Computational studies of the energy of sugar ring distortion show that the β-galactosidase reaction itinerary is driven by energetic considerations in utilization of a (4)H3 transition state with a novel (4)C1-(4)H3-(4)C1 conformation itinerary. To our knowledge, this is the first X-ray crystallographic structural demonstration that the transition state of a natural substrate of a glycosidase has a (4)H3 conformation." @default.
• W1858684328 created "2016-06-24" @default.
• W1858684328 creator A5024247276 @default.
• W1858684328 creator A5055506413 @default.
• W1858684328 date "2015-12-01" @default.
• W1858684328 modified "2023-10-16" @default.
• W1858684328 title "An allolactose trapped at the <i>lacZ</i> β-galactosidase active site with its galactosyl moiety in a ⁴H₃ conformation provides insights into the formation, conformation, and stabilization of the transition state" @default.
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• W1858684328 doi "https://doi.org/10.1139/bcb-2015-0037" @default.
• W1858684328 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/26291713" @default.
• W1858684328 hasPublicationYear "2015" @default.
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