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Reaction mechanisms

Why acetaldehyde kills the DERA aldolase

Dick M, Hartmann R, Weiergräber OH, et al. · Chemical science · 2016

Open access · cc by · source: Europe PMC

Crotonaldehyde, the acetaldehyde aldol product, covalently bridges catalytic K167 to nearby C47; a C47M mutant survives 300 mM acetaldehyde.

Key findings

After 200–300 mM acetaldehyde the enzyme is irreversibly inactivated. Crotonaldehyde forms a Schiff base at K167 and a covalent link to C47. Crotonaldehyde inhibits more than 100-fold more potently than acetaldehyde (1 mM, <1 h). C47 is conserved in 91% of orthologues. C47M keeps 60 ± 5% activity and loses none after 16 h in 300 mM acetaldehyde.

Methodology

Authors combined crystallography, 13C NMR, and a C47M mutation to learn how E. coli DERA dies in concentrated acetaldehyde and how to protect it for synthesis.

Limitations

The work does not deliver a process-scale biocatalytic plant or map every aldehyde side product; only one protective mutation is fully characterized.

How this study connects

Role on claims

Each row is a claim on a concept or method page where this paper supports, challenges, or qualifies the statement. Roles are hand-checked — not a model guess.

  • SupportsNMR Spectroscopymethod

    Mechanism papers use NMR as one reporter among several. ¹³C NMR plus crystallography showed how crotonaldehyde inactivates DERA via K167 and C47; isotope-resolved NMR with ThT and cryo-TEM showed Aβ40 and Aβ42 forming separate homomolecular fibrils after mixed nucleation; ¹H NMR Ka ≈ 75 558 M⁻¹ for DMA binding tracked allosteric opening of a Pt tweezer catalyst.

    Evidence for the claim as stated.

  • SupportsHPLCmethod

    HPLC-adjacent assays in this set also include enzyme activity workups. E. coli DERA is irreversibly inactivated after 200–300 mM acetaldehyde; crotonaldehyde inhibits more than 100-fold more potently (1 mM, <1 h) via K167/C47; C47M keeps 60 ± 5% activity and loses none after 16 h in 300 mM acetaldehyde. LIMK2 PROTAC THNAN69 has DC₅₀ = 1 nM (versus 33 nM for analogue 21b) and 10 nM depletes endogenous LIMK2 — proteomics/Western, not a simple UV chromatogram, carry that selectivity claim.

    Evidence for the claim as stated.

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