ArticleBiochemistry2010
A thiolate anion buried within the hydrocarbon ruler perturbs PagP lipid acyl chain selection.
Article in Biochemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Distinct enzymatic strategies forCritical reviews in biochemistry and molecular biology · 2023Article
- Hydrophobic Characteristic Is Energetically Preferred for Cysteine in a Model Membrane Protein.Biophysical journal · 2019Article
- Salvaging the Thermodynamic Destabilization of Interface Histidine in Transmembrane β-Barrels.Biochemistry · 2018Article
- A divergent Pseudomonas aeruginosa palmitoyltransferase essential for cystic fibrosis-specific lipid A.Molecular microbiology · 2014Article
- Structures of an intramembrane vitamin K epoxide reductase homolog reveal control mechanisms for electron transfer.Nature communications · 2014Article
- Detergent-mediated protein aggregation.Chemistry and physics of lipids · 2013Review
- Amphipathic polymers enable the study of functional membrane proteins in the gas phase.Analytical chemistry · 2012Article
- Inscribing the perimeter of the PagP hydrocarbon ruler by site-specific chemical alkylation.Biochemistry · 2010Article
- PagP crystallized from SDS/cosolvent reveals the route for phospholipid access to the hydrocarbon ruler.Structure (London, England : 1993) · 2010Article
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4 authors.
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Abstract
The Escherichia coli outer membrane phospholipid:lipid A palmitoyltransferase PagP exhibits remarkable selectivity because its binding pocket for lipid acyl chains excludes those differing in length from palmitate by a solitary methylene unit. This narrow detergent-binding hydrophobic pocket buried within the eight-strand antiparallel beta-barrel is known as the hydrocarbon ruler. Gly88 lines the acyl chain binding pocket floor, and its substitution can raise the floor to correspondingly shorten the selected acyl chain. An aromatic exciton interaction between Tyr26 and Trp66 provides an intrinsic spectroscopic probe located immediately adjacent to Gly88. The Gly88Cys PagP enzyme was engineered to function as a dedicated myristoyltransferase, but the mutant enzyme instead selected both myristoyl and pentadecanoyl groups, was devoid of the exciton, and displayed a 21 degrees C reduction in thermal stability. We now demonstrate that the structural perturbation results from a buried thiolate anion attributed to suppression of the Cys sulfhydryl group pK(a) from 9.4 in aqueous solvent to 7.5 in the hydrocarbon ruler microenvironment. The Cys thiol is sandwiched at the interface between a nonpolar and a polar beta-barrel interior milieu, suggesting that local electrostatics near the otherwise hydrophobic hydrocarbon ruler pocket serve to perturb the thiol pK(a). Neutralization of the Cys thiolate anion by protonation restores wild-type exciton and thermal stability signatures to Gly88Cys PagP, which then functions as a dedicated myristoyltransferase at pH 7. Gly88Cys PagP assembled in bacterial membranes recapitulates lipid A myristoylation in vivo. Hydrocarbon ruler-exciton coupling in PagP thus reveals a thiol-thiolate ionization mechanism for modulating lipid acyl chain selection.
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