Conformational behavior of N-acylamino acid oil and N-acylamino acid surfactant in aqueous solution. 2007

Eiko Oshimura, and Yuji Yamashita, and Kazutami Sakamoto
AminoScience Lab., Ajinomoto Co., Inc., Kawasaki, Japan.

The (13)C- and (1)H- NMR spectra of isopropyl N-dodecanoylsarcosinate (SLIP) were measured in CDCl(3), CD(3)OD and in sodium dodecanoylsarcosinate (Sar) aqueous solution. The existence of both cis and trans isomeric forms are observed for SLIP just as for Sar. The trans/cis ratio of SLIP in a dilute CDCl(3) solution is over 3.2, which is indicating that SLIP-trans conformation is more stable in an organic solvent. However, the population of SLIP-trans isomer decreases in aqueous solutions. This may be explained by the interaction of the ester group and N-acyl chain. Addition of SLIP to the water/Sar solution causes the conformational change of both SLIP and Sar. With increasing SLIP concentration, the population of SLIP-trans isomer increases and Sar-cis isomer, which is known to be preferred in the monomer state, also increases. This phenomenon is discussed in the context of the phase transition behavior of SLIP/Sar/water system. At high SLIP and Sar concentration, broadening of (1)H signal relative to 2-CH(2) of Sar occurs both for trans and cis forms, however, broadening of that of Sar N-CH(2) and N-CH(3) is observed only for trans. Analysis of conformation change by NMR was proved to be useful method for phase behavior analysis of an acylamino acid surfactant.

UI MeSH Term Description Entries
D007536 Isomerism The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Isomerisms
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D012521 Sarcosine An amino acid intermediate in the metabolism of choline. Methylglycine,Magnesium Sarcosylate,N-Methylglycine,Sarcosine Hydrochloride,Sarcosine Monosodium Salt,Sodium Sarcosinate,N Methylglycine,Sarcosinate, Sodium,Sarcosylate, Magnesium
D013501 Surface-Active Agents Agents that modify interfacial tension of water; usually substances that have one lipophilic and one hydrophilic group in the molecule; includes soaps, detergents, emulsifiers, dispersing and wetting agents, and several groups of antiseptics. Surface Active Agent,Surface-Active Agent,Surfactant,Surfactants,Tenside,Amphiphilic Agents,Surface Active Agents,Tensides,Active Agent, Surface,Active Agents, Surface,Agent, Surface Active,Agent, Surface-Active,Agents, Amphiphilic,Agents, Surface Active,Agents, Surface-Active
D044367 Phase Transition A change of a substance from one form or state to another. Gas-Liquid-Solid Phase Transitions,Sol-Gel Phase Transition,Gas Liquid Solid Phase Transitions,Gas-Liquid-Solid Phase Transition,Phase Transition, Gas-Liquid-Solid,Phase Transition, Sol-Gel,Phase Transitions,Phase Transitions, Gas-Liquid-Solid,Phase Transitions, Sol-Gel,Sol Gel Phase Transition,Sol-Gel Phase Transitions,Transition, Gas-Liquid-Solid Phase,Transition, Sol-Gel Phase,Transitions, Gas-Liquid-Solid Phase,Transitions, Sol-Gel Phase

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