ArticleActa crystallographica. Section D, Biological crystallography2014
Adherence to Bürgi-Dunitz stereochemical principles requires significant structural rearrangements in Schiff-base formation: insights from transaldolase complexes.
Article in Acta crystallographica. Section D, Biological crystallography, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed, 19 citations in OpenAlex.
- Unexpected Nucleophile Masking in Acyl Transfer to Sterically Crowded and Conformationally Restricted Galactosides.The Journal of organic chemistry · 2023Article
- Anti-Electrostatic Pi-Hole Bonding: How Covalency Conquers Coulombics.Molecules (Basel, Switzerland) · 2022Article
- An enzymatic activation of formaldehyde for nucleotide methylation.Nature communications · 2021Article
- VALD-3, a Schiff base ligand synthesized from o-vanillin derivatives, induces cell cycle arrest and apoptosis in breast cancer cells by inhibiting the Wnt/β-catenin pathway.Scientific reports · 2021Article
- Structural basis for antibiotic action of the BNature chemical biology · 2020Article
- Kinetic Optimization of Lysine-Targeting Covalent Inhibitors of HSP72.Journal of medicinal chemistry · 2019Article
- Biosynthesis of dendroketose from different carbon sources using in vitro and in vivo metabolic engineering strategies.Biotechnology for biofuels · 2018Article
- Isomer activation controls stereospecificity of class I fructose-1,6-bisphosphate aldolases.The Journal of biological chemistry · 2017Article
- Arabinose 5-phosphate covalently inhibits transaldolase.Journal of structural and functional genomics · 2014Article
- Crystal structures of type I dehydroquinate dehydratase in complex with quinate and shikimate suggest a novel mechanism of Schiff base formation.Biochemistry · 2014Article
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4 authors at 1 institution in 1 country.
Funding
Abstract
The Bürgi-Dunitz angle (αBD) describes the trajectory of approach of a nucleophile to an electrophile. The adoption of a stereoelectronically favorable αBD can necessitate significant reactive-group repositioning over the course of bond formation. In the context of enzyme catalysis, interactions with the protein constrain substrate rotation, which could necessitate structural transformations during bond formation. To probe this theoretical framework vis-à-vis biocatalysis, Schiff-base formation was analysed in Francisella tularensis transaldolase (TAL). Crystal structures of wild-type and Lys→Met mutant TAL in covalent and noncovalent complexes with fructose 6-phosphate and sedoheptulose 7-phosphate clarify the mechanism of catalysis and reveal that substrate keto moieties undergo significant conformational changes during Schiff-base formation. Structural changes compelled by the trajectory considerations discussed here bear relevance to bond formation in a variety of constrained enzymic/engineered systems and can inform the design of covalent therapeutics.
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