Synthesis, surface and biological properties of sodium N‐acyl isoleucines

Sreenu, Madhumanchi; Rao, B. V. S. K.; Sujitha, Pombala; Kumar, C. Ganesh

doi:10.1002/ejlt.201300189

Cited by 23 publications

(53 citation statements)

References 51 publications

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“…2.2.1 Typical procedure for the preparation of fatty acid mixtures from coconut oil RCOOH Fatty acid mixtures were prepared from vegetable oils by following our earlier reported method 24 . Coconut oil 54.0 g, 80 mmol was taken into 1 liter of three necked round bottom flask and to this, aqueous NaOH solution 11.2 g, 280 mmol was added drop wise with constant stirring.…”

Section: Synthesis Of Sodium N-acyl Prolinesmentioning

confidence: 99%

“…The fatty acid layer was separated and washed thoroughly with distilled water till neutral and dried under vacuum to obtain the mixtures of fatty acids 49. 8 ty acids NaNAPro Sodium N-acyl prolines were prepared using a method reported in the literature 24 . Briefly, coconut N-acyl prolines 5.0 g, 16.77 mmol were dissolved in ethanol and to this equivalent aqueous NaOH 0.671 g solution was added.…”

Section: Synthesis Of Sodium N-acyl Prolinesmentioning

confidence: 99%

“…The Draves-Clarkson method as described in IS specification BIS-1185, Bureau of Indian Standards, New Delhi, 1957 was used for estimating the wetting time of sodium N-acyl prolines 24 .…”

Section: Wetting Powermentioning

confidence: 99%

“…Modified Hart s method was used for the determination of calcium tolerance of sodium N-acyl prolines 24,26 .…”

Section: Calcium Tolerancementioning

confidence: 99%

“…Considering all these facts, we also synthesized the sodium N-acyl isoleucines as anionic surfactants using a mixture of fatty acids obtained from vegetable oils, namely coconut, palm kernel, palm, jatropha, karanja, Sterculia foetida, castor and high oleic sunflower oils 24 . These vegetable oil-based surfactants exhibited better biological properties and superior surface active properties like calcium tolerance, critical micelle concentration CMC and emulsion stability as compared to the reference surfactant, sodium lauryl sulphate SLS .…”

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Synthesis, Surface Active Properties and Cytotoxicity of Sodium N-Acyl Prolines

2015

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Section: Synthesis Of Sodium N-acyl Prolinesmentioning

confidence: 99%

Section: Synthesis Of Sodium N-acyl Prolinesmentioning

confidence: 99%

“…The Draves-Clarkson method as described in IS specification BIS-1185, Bureau of Indian Standards, New Delhi, 1957 was used for estimating the wetting time of sodium N-acyl prolines 24 .…”

Section: Wetting Powermentioning

confidence: 99%

“…Modified Hart s method was used for the determination of calcium tolerance of sodium N-acyl prolines 24,26 .…”

Section: Calcium Tolerancementioning

confidence: 99%

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Synthesis, Surface Active Properties and Cytotoxicity of Sodium N-Acyl Prolines

2015

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Protocell Self‐Assembly Driven by Sodium Trimetaphosphate

Chen

Yan

Chi

et al. 2023

Chemistry A European J

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The co‐evolution of peptide formation and membrane self‐assembly is considered an essential step in the origin of life. However, more research is required on both processes, particularly on the interaction between prebiotic simple fatty‐acid membranes and peptide synthesis. In this study, the sodium trimetaphosphate (P3m)‐activated peptide formation reaction of phenylalanine (Phe) in an alkaline decanoic acid‐decanol vesicle system was systematically investigated. The experimental results showed that peptide formation could competitively occur with N‐acyl amino acid (NAA) formation. NAA formation did not follow the traditional P3m‐activated peptide formation reaction involving the intermediate cyclic acylphosphoramidate (CAPA). Decanoic acid was activated by P3m to form a mixed anhydride, which then reacted with an amino acid to form the amide NAA. As a kind of membrane‐forming amphiphile, NAA can form vesicles independently and reduce the critical vesicle concentration of the fatty‐acid vesicles. Moreover, 11 other representative amino acids, namely alanine (Ala), aspartic acid (Asp), glutamic acid (Glu), glycine (Gly), isoleucine (Ile), leucine (Leu), proline (Pro), serine (Ser), threonine (Thr), valine (Val), and arginine (Arg), were selected for investigation. All of them reacted with decanoic acid to form NAA via the activation effect of P3m. The abovementioned mechanism involving P3m‐activated carboxylic acid has not been reported in the literature. Our experimental results indicate that the participation of decanoic acid in the P3m activation‐based peptide formation reaction system plays a significant role in the emergence of functionalized protocells. The P3m activation effect can provide diversified raw membrane materials to form and stabilize protocell membranes; moreover, the small peptides, such as Phe‐Leu, formed in the same reaction system can induce the amplification of primitive cells. This implies that synergistic symbiosis between membrane and peptide can be realized via the P3m activation effect.

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Synthesis, Surface Properties and Effect of an Amino Acid Head Group of 11‐(2‐Methoxy‐4‐vinylphenoxy)undecanoicacid‐Based Anionic Surfactants

Darapureddi

Nayak

2016

J Surfact & Detergents

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Our present research describes the surface properties of three biobased anionic surfactant synthesized from vinylguaiacol and 11‐bromo undecanoic acid. To further improve its hydrophobicity and bioavailability, amino acid head group incorporation was carried out. All these synthesized compounds were thoroughly characterized using NMR and mass spectroscopy. The performance properties such as foaming, wetting, emulsification value and calcium tolerance were evaluated. The studied surfactants possess excellent emulsion stability and moderate calcium tolerance as compared to commercially available surfactant sodium lauryl sulfate (SLS). The micelle formation and the thermodynamics involved at the air–water interface were estimated from surface tension measurements. These surfactants showed a higher tendency towards adsorption at the air–water interface than micellization. Dynamic light scattering and steady state fluorescence anisotropy study were carried out to shed light on the bulk micellization properties of the synthesized surfactant. Along with spherical micelles of <5 nm size, larger aggregates (35–84 nm) were observed with higher anisotropy values. FESEM images further confirmed the larger spherical micelles formed by these surfactants. The surfactants formed chiral aggregates above the critical micelle concentration as indicated by circular dichroism spectra. These surfactants may be suitable candidates for additives to detergents to improve their calcium tolerance especially in the case of hard water. Furthermore, a low foaming ability along with high emulsion stability may find these surfactants to be better replacement of the conventional surfactant used as emulsifiers in many industrial applications.

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Synthesis, surface and biological properties of sodium N‐acyl isoleucines

Cited by 23 publications

References 51 publications

Synthesis, Surface Active Properties and Cytotoxicity of Sodium <i>N</i>-Acyl Prolines

Synthesis, Surface Active Properties and Cytotoxicity of Sodium <i>N</i>-Acyl Prolines

Protocell Self‐Assembly Driven by Sodium Trimetaphosphate

Synthesis, Surface Properties and Effect of an Amino Acid Head Group of 11‐(2‐Methoxy‐4‐vinylphenoxy)undecanoicacid‐Based Anionic Surfactants

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