ReviewCurrent opinion in chemical biology2009
Pyridoxal 5'-phosphate: electrophilic catalyst extraordinaire.
Review in Current opinion in chemical biology, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 31 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
31 citing papers in PubMed, 65 citations in OpenAlex.
- Conversion of pyridoxal to pyridoxamine with NHThe FEBS journal · 2025Article
- Key structural features to favour imines over hydrates in water: pyridoxal phosphate as a muse.Chemical science · 2024Article
- Neutron diffraction from a microgravity-grown crystal reveals the active site hydrogens of the internal aldimine form of tryptophan synthase.Cell reports. Physical science · 2024Article
- MpADC, an L-aspartate-α-decarboxylase, from Myzus persicae, that enables production of β-alanine with high yield by whole-cell enzymatic catalysis.Biotechnology for biofuels and bioproducts · 2023Article
- Revealing protonation states and tracking substrate in serine hydroxymethyltransferase with room-temperature X-ray and neutron crystallography.Communications chemistry · 2023Article
- Alkylcysteine Sulfoxide C-S Monooxygenase Uses a Flavin-Dependent Pummerer Rearrangement.Journal of the American Chemical Society · 2023Article
- An N⋯H⋯N low-barrier hydrogen bond preorganizes the catalytic site of aspartate aminotransferase to facilitate the second half-reaction.Chemical science · 2022Article
- Follicular Fluid: A Powerful Tool for the Understanding and Diagnosis of Polycystic Ovary Syndrome.Biomedicines · 2022Review
- Peculiarities of promiscuous L-threonine transaldolases for enantioselective synthesis of β-hydroxy-α-amino acids.Applied microbiology and biotechnology · 2021Review
- Theoretical and Mechanistic Validation of Global Kinetic Parameters of the Inactivation of GABA Aminotransferase by OV329 and CPP-115.ACS chemical biology · 2021Article
- Biocatalytic, Stereoselective Deuteration of α-Amino Acids and Methyl Esters.ACS catalysis · 2020Article
- Engineering of a Red Fluorogenic Protein/Merocyanine Complex for Live-Cell Imaging.Chembiochem : a European journal of chemical biology · 2020Article
- Carbon Acidity in Enzyme Active Sites.Frontiers in bioengineering and biotechnology · 2019Article
- Direct visualization of critical hydrogen atoms in a pyridoxal 5'-phosphate enzyme.Nature communications · 2017Article
- Versatility of Pyridoxal Phosphate as a Coating of Iron Oxide Nanoparticles.Nanomaterials (Basel, Switzerland) · 2017Article
- Substituent Effects on Carbon Acidity in Aqueous Solution and at Enzyme Active Sites.Synlett : accounts and rapid communications in synthetic organic chemistry · 2017Article
- Direct evidence that an extended hydrogen-bonding network influences activation of pyridoxal 5'-phosphate in aspartate aminotransferase.The Journal of biological chemistry · 2017Article
- NMR Crystallography of a Carbanionic Intermediate in Tryptophan Synthase: Chemical Structure, Tautomerization, and Reaction Specificity.Journal of the American Chemical Society · 2016Article
- Aspartate aminotransferase: an old dog teaches new tricks.Archives of biochemistry and biophysics · 2014Review
- Structural basis for the broad specificity of a new family of amino-acid racemases.Acta crystallographica. Section D, Biological crystallography · 2014Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
Abstract
Studies of nonenzymatic electrophilic catalysis of carbon deprotonation of glycine show that pyridoxal 5'-phosphate (PLP) strongly enhances the carbon acidity of alpha-amino acids, but that this is not the overriding mechanistic imperative for cofactor catalysis. Although the fully protonated PLP-glycine iminium ion adduct exhibits an extraordinary low alpha-imino carbon acidity (pK(a)=6), the more weakly acidic zwitterionic iminium ion adduct (pK(a)=17) is selected for use in enzymatic reactions. The similar alpha-imino carbon acidities of the iminium ion adducts of glycine with 5'-deoxypyridoxal and with phenylglyoxylate show that the cofactor pyridine nitrogen plays a relatively minor role in carbanion stabilization. The 5'-phosphodianion group of PLP likely plays an important role in catalysis by providing up to 12 kcal/mol of binding energy that may be utilized for transition state stabilization.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.