ArticleThe Journal of organic chemistry2018
A Synthetic Isoprenoid Lipoquinone, Menaquinone-2, Adopts a Folded Conformation in Solution and at a Model Membrane Interface.
Article in The Journal of organic chemistry, 2018. 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, 20 citations in OpenAlex.
- Vitamin K (Menaquinone) from marine Kocuria sp. RAM1: optimization, characterization and potential in vitro biological activities.Microbial cell factories · 2025Article
- Chemistry of Lipoquinones: Properties, Synthesis, and Membrane Location of Ubiquinones, Plastoquinones, and Menaquinones.International journal of molecular sciences · 2022Review
- Electron Transport Lipids Fold Within Membrane-Like Interfaces.Frontiers in chemistry · 2022Article
- Interactions of Truncated Menaquinones in Lipid Monolayers and Bilayers.International journal of molecular sciences · 2021Article
- The Interfacial Interactions of Glycine and Short Glycine Peptides in Model Membrane Systems.International journal of molecular sciences · 2020Article
- In Silico/In Vitro Hit-to-Lead Methodology Yields SMYD3 Inhibitor That Eliminates Unrestrained Proliferation of Breast Carcinoma Cells.International journal of molecular sciences · 2020Article
- Synthesis of Naphthoquinone Derivatives: Menaquinones, Lipoquinones and Other Vitamin K Derivatives.Molecules (Basel, Switzerland) · 2020Review
- Synthesis and Characterization of Partially and Fully Saturated Menaquinone Derivatives.ACS omega · 2018Article
- Structure Dependence of Pyridine and Benzene Derivatives on Interactions with Model Membranes.Langmuir : the ACS journal of surfaces and colloids · 2018Article
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Authors and funding
9 authors at 1 institution in 1 country.
Funding
Abstract
Menaquinones (naphthoquinones, MK) are isoprenoids that play key roles in the respiratory electron transport system of some prokaryotes by shuttling electrons between membrane-bound protein complexes acting as electron acceptors and donors. Menaquinone-2 (MK-2), a truncated MK, was synthesized, and the studies presented herein characterize the conformational and chemical properties of the hydrophobic MK-2 molecule. Using 2D NMR spectroscopy, we established for the first time that MK-2 has a folded conformation defined by the isoprenyl side-chain folding back over the napthoquinone in a U-shape, which depends on the specific environmental conditions found in different solvents. We used molecular mechanics to illustrate conformations found by the NMR experiments. The measured redox potentials of MK-2 differed in three organic solvents, where MK-2 was most easily reduced in DMSO, which may suggest a combination of solvent effect (presumably in part because of differences in dielectric constants) and/or conformational differences of MK-2 in different organic solvents. Furthermore, MK-2 was found to associate with the interface of model membranes represented by Langmuir phospholipid monolayers and Aerosol-OT (AOT) reverse micelles. MK-2 adopts a slightly different U-shaped conformation within reverse micelles compared to within solution, which is in sharp contrast to the extended conformations illustrated in literature for MKs.
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