Aggregate morphology and hydrogenation reactivity of functionalized bilayer membrane composed of peptide lipid having NADH activity.
スポンサーリンク
概要
- 論文の詳細を見る
A peptide lipid bearing the 1,4-dihydronicotinamide moiety, <I>N</I>,<I>N</I>-dihexadecyl-<I>N</I><SUP>α</SUP>-[1-(6-trimethylammoniohexyl)-1,4-dihydro-3-pyridylcarbonyl]-L-alaninamide bromide [N<SUP>+</SUP>C<SUB>6</SUB>(NAH)Ala2C<SUB>16</SUB>], and its dehydrogenated form, <I>N</I>,<I>N</I>-dihexadecyl-<I>N</I><SUP>α</SUP>-[1-(6-trimethylammoniohexyl)pyridinium-3-ylcarbonyl]-L-alaninamide chloride bromide [N<SUP>+</SUP>C<SUB>6</SUB>(NA<SUP>+</SUP>)Ala2C<SUB>16</SUB>], were prepared. Both lipids formed bilayer membranes when they were dispersed in aqueous media, and the 1,4-dihydronicotinamide and nicotinamide moieties of the respective lipid molecules were placed in the so-called hydrogen-belt domain upon membrane formation. In an aqueous dispersion of the latter dicationic lipid, relatively small multilayered vesicles were predominantly formed while the related monocationic lipids bearing the same double alkyl chain composed much larger vesicles and/or lamellae. Formation of the charge-transfer (CT) complex of the nicotinamide moiety of N<SUP>+</SUP>C<SUB>6</SUB>(NA<SUP>+</SUP>)Ala2C<SUB>16</SUB> with 3-indolylacetic acid was much enhanced in the membrane through tight electrostatic interaction. The bilayer membrane composed of N<SUP>+</SUP>C<SUB>6</SUB>(NAH)Ala2C<SUB>16</SUB> acted as a potential reductant toward anionic substrates in aqueous media. The high reactivity is gained primarily by the effective incorporation of the substrates into the hydrogen-belt domain through electrostatic, hydrogen bonding, and CT interactions and partly by the proximity effect which becomes valid between the 1,4-dihydronicotinamide moiety and the bound substrate molecule.
- 公益社団法人 日本化学会の論文
著者
-
Murakami Yukito
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
-
KIKUCHI Jun-ichi
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University
-
Nishida Koji
Department Of Cardiology Chikamori Hospital
-
Nakano Akio
Department of Chemistry, Faculty of Science, Kyushu University
関連論文
- Preparation and Characterization of Novel Cage-type Cyclophanes Having Three or Four Bridging Dipeptide Segments
- Catalytic Performance of a Supramolecular Bienzyme Complex Formed with Artificial Aminotransferase and Natural Lactate Dehydrogenase
- Stereoselective Synthesis of β-Phenylserine from Glycine and Benzaldehyde as Mediated by Catalytic Bilayer Membranes, Artificial Vitamin B_6-dependent Enzymes
- pH-Responsive Molecular Recognition by a Water-soluble Cyclophane Bearing L-Aspartate Moieties
- Photolysis of Hydrophobic Vitamin B_ Derivatives Covalently Bound to Lipid in Aqueous Media
- Enantioselective Alkylation of Hydrophobic Vitamin B_ Bearing Binaphthyl Moiety
- Discrimination of Steroid Hormones by Novel Cage-type Azacyclophanes Bearing Chiral Binding Sites
- β-Replacement Reaction in an Asymmetric Site Provided by an Artificial Enzyme Composed of a Hydrophobic Vitamin B_6 and Peptide Lipids
- Enantioselective β-Replacement Reaction Mediated by an Artificial Enzyme Composed of a Hydrophobic Vitamin B_6, Chiral Bilayer-forming Lipids, and Copper(II) Ions
- Synthetic Cationic Amphiphile for Liposome-Mediated DNA Transfection with Less Cytotoxicity
- Primary carcinoid tumor in a horseshoe kidney
- PE-045 Clinical Results of Drug-Eluting Stents and Bare-Metal Stents in Large (more than 3.5mm) Coronary Artery(PE008,Coronary Revascularization, PCI (DES) 1 (IHD),Poster Session (English),The 73rd Annual Scientific Meeting of The Japanese Circulation Soc
- Promotion of Reductive Elimination Reaction of Diorgano (2, 2' -bipyridyl) nickel (II) Complexes by Electron-Accepting Aromatic Compounds, Lewis Acids, and Bronsted Acids
- Control of Reductive Elimination and Acidolysis of Diarylnickel(II) Complexes by the Kind of Bronsted Acid and the Presence of Oxygen
- Topics on symbolic Rees algebras for space monomial curves
- The Gorensteinness of symbolic Rees algebras for space curves
- Electric Field Dependence of Variance in Helicoidal Pitch Distribution and of Light Transmittance in the Ferroelectric Liquid Crystal DOBAMBC
- Optical Absorption of CdI2 Single Molecule and Clusters Incorporated into Zeolite Na-FAU
- The mechanism of spinal cord regeneration promoted by neural progenitor cell transplantation
- Therapeutic Effects With Magnetic Targeting of Bone Marrow Stromal Cells in a Rat Spinal Cord Injury Model
- Aggregation behavior of amphiphiles functionalized with dipeptide segments and enantioselective ester hydrolysis in their bilayer membranes.
- Copper(II)-catalyzed transamination between pyruvate and hydrophobic pyridoxamine embedded in synthetic bilayer membranes.
- Catalytic efficiency of functionalized vesicles in the transamination of pyridoxal-5'-phosphate with a hydrophobic amino acid.
- Macrocyclic enzyme model system. Kinetic activity of (20)paracyclophane bearing 1,4-dihydronicotinamide and 2-pyridinecarboxylic acid moieties as effected by zinc ion.
- Functionalized bilayer membranes as artificial tryptophan synthase. Characterization of catalytic efficiency, substrate specificity, and reaction selectivity.
- Transition-metal complexes of pyrrole pigments. XIX. Electrochemical and coordination behaviors of (5,10,15,20-tetraphenylporphinato)niobium(V) complexes.
- A macrocyclic enzyme model system. An electrostatic-hydrophobic double-field catalysis by a [20]paracyclophane in the deacylation of p-nitrophenyl hexadecanoate.
- Transition-metal complexes of pyrrole pigments. XVII. Preparation and spectroscopic properties of corrole complexes.
- Transition-metal complexes of pyrrole pigments. XXI. One-electron oxidation of water mediated by a cobalt(III)-tetradehydrocorrin complex.
- Syntheses of Organic Phosphates. II. 3-Hydroxy-2-pyridylmethyl, 6-Methyl-2-pyridylmethyl, 3-Pyridyl and 8-Quinolyl Phosphate
- A potent pyridoxal model capable of promoting transamination and .BETA.-elimination of amino acids.
- Substrate selectivity of artificial transaminase constituted with functionalized bilayer membrane.
- Aggregate morphology of peptide lipids having hydroxyl groups : Molecular basis for formation of inverted hexagonal, inverted cubic, bilayer, and micellar phases.
- Total Synthesis of Natural Acetylenic Analogues of Isorenieratene and Renieratene
- Catalytic efficiency of cationic micellar catalysts bearing a mercapto group as the reaction center.
- Hydrophobic vitamin B12. III. Incorporation of hydrophobic vitamin B12 derivatives into single-compartment vesicles and their alkylation in various molecular aggregates.
- Hydrophobic vitamin B12. V Electrochemical carbon-skeleton rearrangement as catalyzed by hydrophobic vitamin B12 : Reaction mechanisms and migratory aptitude of functional groups.
- Catalytic Functions of Artificial Enzyme Composed of Simple Vitamin B12 Model and Synthetic Bilayer Membrane.
- Hydrophobic vitamin B12. II. Coordination geometry and redox behavior of heptamethyl cobyrinate in nonaqueous media.
- Macrocyclic enzyme model systems. Catalytic activity of cyclic peptides involving hydrophobic segments.
- Transformation between lamellar and nonlamellar aggregates formed with synthetic peptide lipids.
- Aggregate morphology and hydrogenation reactivity of functionalized bilayer membrane composed of peptide lipid having NADH activity.
- Fusogenic behavior of single-walled vesicles composed of synthetic peptide lipids.
- Hydrophobic vitamin B12. I. Preparation and axial ligation behavior of hydrophobic vitamin B12r.
- Transition-metal Complexes of Pyrrole Pigments. X. Divalent and Trivalent Manganese Chelates of Dipyrromethenes
- Transition-metal Complexes of Pyrrole Pigments. III. Copper(II) and Zinc(II) Complexes of 1,19-Dideoxy-8,12-dicarbethoxy-1,3,7,13,17,19-hexamethylbiladiene-ac
- Solvolysis of Organic Phosphates. VIII. γ-Elimination in the Spontaneous Hydrolysis of 2-Chloro-3-pyridylmethyl Phosphate
- Solvolysis of Organic Phosphates. IV. 3-Pyridyl and 8-Quinoly Phosphates as Effected by the Presence of Metal Ions
- Transition-metal complexes of pyrrole pigments. XII. Optical and magnetic resonance spectra of the cobalt(II) and nickel(II) complexes of 1,19-disubstituted tetradehydrocorrins.
- Transition-metal complexes of pyrrole pigments. XIII. Reduction and coordination behaviors of the cobalt(II) complexes of 1,19-disubstituted tetradehydrocorrins as demonstrated by the presence of various bases.