Sodium Salts Of Amino Acids Research Articles

Antioxidant activity of amino acid sodium and potassium salts in vegetable oils at frying temperatures

AbstractPrevious studies reported that several amino acids had strong antioxidant activity in vegetable oils under frying conditions. In this study, amino acids were converted to their sodium or potassium salts, and a heating study was conducted with 5.5 mM amino acid salts in soybean oil (SBO) at 180°C. Sodium salts of amino acids including alanine, phenylalanine, and proline and disodium glutamate had significantly stronger antioxidant activity than the corresponding amino acids, and potassium salts had stronger antioxidant activity than sodium salts. Potassium salts of alanine and phenylalanine more effectively retained tocopherols in SBO than the corresponding amino acids during heating. Phenylalanine potassium salt had stronger antioxidant activity than phenylalanine in other vegetable oils including olive, high oleic soybean, canola, avocado, and corn oils. Phenylalanine potassium salt at 5.5 mM more effectively prevented oil oxidation than tert‐butyl hydroquinone, a synthetic antioxidant, at its legal concentration limit (0.02%) indicating its feasibility as a new antioxidant for frying.

Assessment of the stability of amino acid complexes of heavy metals to biodegradation in the aquatic environment

Sodium salts of amino acids in solution have an alkaline reaction, which makes it possible to effectively bind metals into complex compounds, since in an alkaline medium, under the action of hydroxyl ions, the dissociation of amine groups is suppressed, and carboxyl groups remain dissociated, charging negatively, and behave like an anion.In our experiments, we used an amino acid-based reagent. When processing various environments (objects) contaminated with heavy metals (HM) with this reagent, HM amino acid complexes are formed. In our experiments, we used an amino acid-based reagent. With processing various environments (objects) contaminated with heavy metals (HM) with this reagent are formed HM amino acid complexes.Model experiments to assess the effect of microorganisms under aerobic conditions on the stability of amino acid complexes of heavy metals. After biodegradation of solutions with TM complexes, no more than 2-3% of heavy metals pass through the filter, which is ten times less than from untreated with the reagent solution.

Structural - chemical studies of the destruction of organochlorine compounds

Polychlorinated biphenyls (PCB) are persistent organic pollutants used worldwide up 1990s. Although their use has been heavily restricted, PCB can be found in contaminated soils and sediments. Conducted structural-chemical studies of the destruction of polychlorinated biphenyl salts of amino acids in the soil. The effect of concentrated solutions of sodium salts of amino acids on soil particles has been investigated using FTIR spectroscopy as a means of identifying PCBs in the soil, controlling the interactions of PCBs with amino acid salts. The reaction products —C— substituted biphenyl polyamino polyacetic acids and their salts are soluble in water and extracted from particles on the surface of which polychlorinated biphenyls are adsorbed.

Formation of the reduced form of furaneol® (2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one) during the Maillard reaction through catalysis of amino acid metal salts

Under pyrolytic conditions the acidity/basicity of Maillard reaction mixtures can be controlled through the use of hydrochloride or sodium salts of amino acids to generate a diversity of products. When the degradation of glucose was studied under pyrolytic conditions using excess sodium glycinate the reaction was found to generate a major unknown peak having a molecular ion at m/z 130. Subsequent in-depth isotope labelling studies indicated that acetol was an important precursor of this compound under pyrolytic and aqueous heating conditions. The dimerisation and cyclisation of acetol into 2,5-dimethyl-4-hydroxy-tetrahydrofuran-3-one was found to be catalysed by amino acid metal salts. Also, ESI/qTOF/MS studies indicated that the unknown peak has expected molecular formula of C6H10O3. Finally, a peak having the same retention time and mass spectrum was also generated pyrolytically when furaneol® was reduced with NaBH4 confirming the initial hypothesis regarding the unknown peak to be the reduced form of furaneol®.

Synthesis, surface and micellar properties of sodium N-oleoyl amino acids

Oleic acid-based amphiphilic surfactants were synthesized using three amino acids namely isoleucine (Ile), phenylalanine (Phe), and proline (Pro) containing aliphatic, aromatic and alicyclic moiety as polar head group. N-Oleoyl amino acids were prepared using Schotten-Baumann reaction by reacting sodium salt of amino acid with oleoyl chloride. The products were thoroughly characterized by chromatographic and spectral techniques, and were evaluated for surface active properties like surface tension, critical micelle concentration (CMC), wetting time, calcium tolerance, emulsion stability and foaming characteristics. These surfactants exhibited better surface activity, calcium tolerance and emulsion stability compared to commercially available surfactant sodium lauryl sulphate (SLS). All theses surfactants showed much lower CMC values (0.7–4.8μmol/L) compared to the similar hydrophobic chain length surfactant. Micellar aggregation numbers (Nss) for sodium N-oleoyl isoleucines (SNOIle), sodium N-oleoyl phenylalanine (SNOPhe) and sodium N-oleoyl proline (SNOPro) were found to be 15, 17 and 20. With the help of steady state fluorescence anisotropy value along with fluorescence life time of 1, 6-diphenyl-1,3,5-hexatriene (DPH) probe, the SNOIle, SNOPhe and SNOPro surfactant micelle's hydrophobic core viscosity (microviscosity) was found to be 12.75, 11.7 and 6.16MPas respectively. Spherical micellar structure was observed for these surfactants in the transmission electron microscopy (TEM) images.

Total Synthesis of Jadomycins B, S, T, and ILEVS1080

Sweetening up jadomycin A: The first total synthesis of jadomycins B, S, T, and ILEVS1080 has been achieved, featuring construction of the unique 8H-benz[b]oxazolo[3,3-f]phenanthridine skeleton by biomimetic condensation of a quinone aldehyde with amino acid sodium salts and elaboration of the glycosides by Mitsunobu condensation (see figure).

REACTIONS OF 5-METHYLENE-1,3-DIOXOLAN-2-ONES WITH AMINES. SYNTHESIS OF 2-OXAZOLIDINONES

The reaction of 5-methylene-1,3-dioxolan-2-ones with aromatic or aliphatic amines as well as with the sodium salts of amino acids leads to 4-hydroxy-2-oxazolidinones. The reaction conditions depend on the basicity of the amines. The use of o phenylenediamine in this reaction leads to the formation of a new heterocyclic system. Authors: N. B. Chernysheva, A. A. Bogolyubov, and V. V. Semenov. English Translation in Chemistry of Heterocyclic Compounds , 1999, 35 (2), pp 216-224 http://link.springer.com/article/10.1007/BF02251714

FMOC-Amino Acid Surfactants: Discovery, Characterization and Chiroptical Spectroscopy

The sodium salts of amino acids with hydrophobic fluorenyl methyloxy carbonyl (FMOC) group and short alkyl side chains are found to have surfactant properties. This was ascertained first through visual observation of concentration dependent solution behavior and then confirmed by tensiometry measurements. The critical micelle concentrations (CMCs) for the sodium salts of FMOC-l-valine, FMOC-L-leucine, and FMOC-L-isoleucine have been determined to be ~0.1 M. The sodium salt of FMOC-l-norleucine forms a gel at >0.2 M. Powder X-ray diffraction measurements indicated that these surfactants adopt bilayer structures. Three different chiroptical spectroscopic properties, namely optical rotation, electronic circular dichroism, and vibrational circular dichroism, are presented for these surfactants. The specific rotation is found to exhibit an unprecedented increase with concentration beyond CMC. This observation opens up a new area of research relating the concentration dependent increase in specific rotation to the size and shape of aggregates formed by the surfactants.

Amino acids as suitable N-nucleophiles for the aza-Michael reaction of vinylphosphoryl compounds in water

Application of water as a sole solvent promotes the aza-Michael reaction of diethyl vinylphosphonate and diphenylvinylphosphine oxide with α-substituted amino acid sodium salts generated in situ to afford the corresponding β-aminophosphonates and β-aminophosphine oxides in excellent yields and of high purity. The approach is equally suitable for the synthesis of both racemic and optically active compounds. In the case of glycine, the mono and bis(phosphonoethyl)-substituted products are formed in 6:4 ratio and when using a stoichiometric amount of the reactants, N,N-bis[2-(diethoxyphosphoryl)ethyl]glycine was the only product. In contrast, to perform the double phosphonoethylation of d,l-alanine, prolonged heating of the reaction mixture was required.

Macromolecular recognition by cyclodextrins. Interaction of cyclodextrins with poly( N-acryloyl-amino acids)

The interactions of cyclodextrins (CDs) with poly( N-acryloyl-amino acids) (pAXaa) were investigated by 1H NMR and two dimensional nuclear Overhauser effect spectroscopy (2D NOESY) to elucidate the effect of attachment of amino acid residues to the polymer chain. Using the 1H NMR data measured at varying pAXaa concentrations, apparent association constants ( K) were roughly estimated for the CDs/pAXaa systems. These apparent K values indicated that α-CD interacted with poly( N-acryloylphenylalanine) and with poly( N-acryloyltyrosine) and β-CD and γ-CD interacted with poly( N-acryloyltryptophan). Comparison of these apparent K values with those for the model compounds, i.e., amino acid sodium salts, revealed that the effect of attachment of amino acid residues to the polymer chain was stronger for a smaller amino acid residue.

ChemInform Abstract: Reactions of 5-Methylene-1,3-dioxolan-2-ones with Amines. Synthesis of 2-Oxazolidinones.

The reaction of 5-methylene-1,3-dioxolan-2-ones with aromatic or aliphatic amines as well as with the sodium salts of amino acids leads to 4-hydroxy-2-oxazolidinones. The reaction conditions depend on the basicity of the amines. The use of o-phenylenediamine in this reaction leads to the formation of a new heterocyclic system.

Synthesis of chiral monoaza-15-crown-5 ethers from a chiral amino alcohol and enantiomeric recognition of potassium and sodium salts of amino acids

The enantiomeric recognition of chiral monoaza-crown ethers for amino acids as their sodium and potassium salts has been investigated by UV–vis. The highest discrimination was observed for TrpK ( d/ l = 6.47). The reversed enantioselectivity of chiral monoaza-crown ether II was observed for TrpK.

Synthesis of chiral diaza 18-crown-6 ethers from chiral amines and molecular recognition of potassium and sodium salts of amino acids

A practical synthesis of chiral amine precursors 3 and 4 and chiral diaza 18-crown-6 ethers 5, 6 and 7 starting from chiral amines are reported. The molecular recognition of these chiral crown ethers for amino acids potassium and sodium salts has been characterized by UV–vis. The selectivity order is Phe>Thr>Ala. In the case of 6 the cavity of the macrocycle plays an important role in recognition.

Use of nucleic acids in the mobile phase for the determination of ascorbic acid in foods by high-performance liquid chromatography with electrochemical detection

The sodium salts of amino acids, nucleic acids and organic acids were examined in a new mobile phase for the determination of ascorbic acid (AA) in foods. It was possible to use disodium guanosine-5′-monophosphate (GMP) (20 m M GMP, pH 2.1) in a new mobile phase after comparison of five mobile phases. The proposed method is simple, rapid (analysis time: ca. 6 min), sensitive (detection limit: ca. 0.1 ng per injection (5 μl) at a signal-to-noise ratio of 3), highly selective and reproducible [relative standard deviation: ca. 2.7% ( n=7)]. The calibration graph of AA was linear in the range of 0.1 to 50 ng per injection (5 μl). Recovery of AA was over 90% by the standard addition method.

Reactions of 5-methylene-1,3-dioxolan-2-ones with amines. Synthesis of 2-oxazolidinones

The reaction of 5-methylene-1,3-dioxolan-2-ones with aromatic or aliphatic amines as well as with the sodium salts of amino acids leads to 4-hydroxy-2-oxazolidinones. The reaction conditions depend on the basicity of the amines. The use of o-phenylenediamine in this reaction leads to the formation of a new heterocyclic system.

Stereoselective Preparation and Characterization of [Cr(amino acidato)2(amino acidato-N)(Me2SO)] Complexes

Abstract New complexes of the type [Cr(AA)2(AA-N)(Me2SO)], where AA stands for l-amino acidato ligands (valinato, isoleucinato, and leucinato) and AA-N represents monodentate l-amino acidato ligands with an amino nitrogen as a donor atom, were prepared by heating mixtures of Cr(NO3)3·9H2O and sodium salts of amino acids in Me2SO. For all the amino acids used, only complexes of the type (+)546-[Cr(AA)2(AA-N)(Me2SO)] were obtained. The presence of a Me2SO molecule as a ligand was shown by the IR spectra of the crystals of the complexes. The bis-type complexes with l-valine and l-isoleucine were converted to (−)546-isomers in MeOH and the resulting products were isolated. All the new complexes were confirmed to have facial configuration, [Cr(O)3(N)3] from their UV-vis absorption spectra, as well as the corresponding tris-type complexes, [Cr(AA)3].

Removal of aldehydes by amino acids and their salts in ambient air

AbstractThe removal of gaseous aldehydes by amino acids and by their sodium salts and hydrochlorides was studied in ambient air with the relative humidity of 30% at 25°C. Amino acid sodium salts, diamino acids, sodium p‐aminobenzoate (PABANa), and o‐aminobenzoate (OABANa), and p‐aminobenzoic acid (PABA) on sepiolite, both having a carboxylato functionality (COO−) together with an amino (NH2) group, were highly reactive with aldehydes. In contrast, PABA which has free carboxylic acid functionality (COOH: dimeric) was not so reactive with aldehydes. Normal amino acids and their hydrochlorides having ammonio (NH2+) and COO− or COOH (dimeric) groups were less reactive with aldehydes. The reactivity was closely related to the degree of dissociation of carboxylate anion; as the degree of dissociation increases, the compound becomes more reactive. p‐Aminobenzoic acid hydrochloride (PABA · HCl), having NH3+ and COOH (monomeric) groups, was the most reactive (with ethanal) of all the amino acids and their salts examined. Amino acid sodium salts, diamino acid, PABANa, OABANa, and PABA on sepiolite are proved to be excellent removers of aldehydes in ambient air. Among them, PABA · HCl is particularly good for ethanal.

Synthesis of alternating polydepsipeptides by ring‐opening polymerization of morpholine‐2,5‐dione derivatives

AbstractPolydepsipeptides with alternating α‐hydroxy acid and α‐amino acid residues were synthesized by ring‐opening polymerization of morpholine‐2,5‐dione derivatives. The polymerizations were performed in the melt using stannous octoate as an initiator. Molecular weights of the polydepsipeptides obtained ranged from 0,9 · 104 to 7,4 · 104. Morpholine‐2,5‐dione derivatives unsubstituted at the 6‐position gave polymers with the highest molecular weights. Poly((S)‐alanine‐alt‐glycolic acid) was semi‐crystalline, whereas all other polydepsipeptides synthesized were amorphous. Morpholine‐2,5‐dione derivatives were synthesized by N‐acylation of glycine, (S)‐alanine or (S)‐valine with chloroacetyl chloride or (R,S)‐2‐bromopropionyl bromide, followed by ring‐closure of N‐(2‐halogenacyl)‐amino acid sodium salts in the melt in 4 to 83% yield. Low yields in the cyclization reaction of N‐(2‐halogenacyl)‐(S)‐valine were accompanied by the formation of the corresponding polydepsipeptides in 13 to 46% yield, with molecular weights ranging from 3,3 · 104 to 4,9 · 104.

Some Potential Anticancer Palladium(II) Complexes of 2,2'-bipyridine and amino acids

Nine new palladium(II) complexes of the formula [Pd(bipy)(AA)] n+ (where bipy is 2,2'-bipyridine, AA is an anion of L-cysteine, L-aspartic acid, L-glutamic acid, L-methionine, L-histidine, L-arginine, L-phenylalanine, L-tyrosine, or L-tryptophan, and n = 0 or 1) have been synthesized by interaction of [Pd(bipy)Cl 2] with an appropriate sodium salt of amino acid in water. These palladium(II) complexes have been characterized by chemical analysis and by visible, infrared, and 1H NMR spectroscopy. The modes of binding of amino acids in these palladium complexes have been ascertained by infrared and 1H NMR spectroscopy. The molar conductances of these complexes in water suggest that they are either nonelectrolytes or 1:1 electrolytes. These palladium complexes have shown growth inhibition against L1210 lymphoid leukemic, P388 lymphocytic leukemic, Sarcama 180, and Ehrlich ascites tumor cells. Some of these complexes show I.D. 50 values comparable to or lower than cis-diamminedichloroplatinum(II)

Some mixed-ligand palladium(II) complexes of 2,2'-bipyridine and amino acids as potential anticancer agents

Eight new palladium complexes of the formula [Pd(bipy)(AA)]Cl 1 or 2 H 2O (where bipy is 2,2'-bipyridine and AA is an anion of glycine, L-alanine, L-leucine, L-proline, L-serine, L-lysine, L-asparagine, or L-glutamine) have been synthesized by reaction of [Pd(bipy)Cl 2] with an appropriate mono sodium salt of amino acid in water. These complexes have been characterizied by chemical analysis and by visible, infrared, and 1H NMR spectroscopy. The detailed 1H NMR and infrared spectral studies of these complexes ascertain the mode of binding of amino acids to palladium through nitrogen of terminal -NH 2 group and oxygen of terminal -COO − group. The molar conductance values of these complexes in water suggest them to be 1:1 electrolytes. These complexes have also shown growth inhibition against L1210 lymphoid leukemic, P388 lymphocytic leukemic, Sarcoma 180, and Ehrlich ascitic tumor cells. Some of these complexes show better 50% inhibitory dose values than cis-diamminedichloroplatinum(II).