- Potential grape-derived contributions to volatile ester concentrations in wine
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Grape composition affects wine flavour and aroma not only through varietal compounds, but also by influencing the production of volatile compounds by yeast. C9 and C12 compounds that potentially influence ethyl ester synthesis during fermentation were studied using a model grape juice medium. It was shown that the addition of free fatty acids, their methyl esters or acyl-carnitine and acyl-amino acid conjugates can increase ethyl ester production in fermentations. The stimulation of ethyl ester production above that of the control was apparent when lower concentrations of the C9 compounds were added to the model musts compared to the C12 compounds. Four amino acids, which are involved in CoA biosynthesis, were also added to model grape juice medium in the absence of pantothenate to test their ability to influence ethyl and acetate ester production. β-Alanine was the only one shown to increase the production of ethyl esters, free fatty acids and acetate esters. The addition of 1 mg·L-1 β-alanine was enough to stimulate production of these compounds and addition of up to 100 mg·L-1 β-alanine had no greater effect. The endogenous concentrations of β-alanine in fifty Cabernet Sauvignon grape samples exceeded the 1 mg·L-1 required for the stimulatory effect on ethyl and acetate ester production observed in this study.
- Boss, Paul K.,Pearce, Anthony D.,Zhao, Yanjia,Nicholson, Emily L.,Dennis, Eric G.,Jeffery, David W.
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Read Online
- First report of phase selective gelation of oil from oil/water mixtures. Possible implications toward containing oil spills
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From a two-phase mixture of water and oil (either commercial fuel or pure organic solvent), a simple amino acid derivative, N-lauroyl-L-alanine has been shown to be able to gelate the oil phase selectively; SEM and FT-IR provided molecular level insights into the process of gelation.
- Bhattacharya,Krishnan-Ghosh
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Read Online
- Synthesis method of N-lauroyl amino acid salt
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The invention provides a synthesis method of N-lauroyl amino acid salt, which comprises the following steps: mixing amino acid, alkali or alkali metal salt and lauramide into a reaction container according to a certain proportion, and arranging a tail gas receiving device on the reaction container; stirring and reacting for a certain time at a certain temperature; after the reaction is finished, acidifying the reaction mixture by using a hydrochloric acid solution to precipitate the product, filtering and collecting the precipitate to obtain a purified product; carrying out forced air drying on the purified product to remove moisture, so as to obtain a dried product; and dissolving the product with ethanol, adding an alkali solution at a certain temperature, stirring to react for a period of time, cooling to crystallize, and carrying out suction filtration to obtain the lauroyl amino acid salt. Other substances are not used as solvents, the problems of too high production and waste treatment cost and environmental pollution caused by the fact that a large amount of solvents (such as acetone and the like) are used at present are solved, and the method is a green and economical synthesis method and has wide market prospects and social benefits.
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Paragraph 0029-0033; 0039-0044
(2021/07/14)
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- Preparation method and application of N-lauroyl-L-alanine
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The invention discloses a preparation method of N-lauroyl-L-alanine. The preparation method comprises the following steps: preparing L-alanine salt, preparing pasty N-lauroyl-L-alanine salt, and preparing an N-lauroyl-L-alanine crude product and the like. The invention further provides application of amino acid in the daily chemical field and industries such as agriculture and medicines. The aminoacid provided by the invention has high performance, and has an obvious effect in the aspects of bacterium inhibition, pesticide removal, peculiar smell elimination and the like.
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Paragraph 0166; 0120; 0121; 0122; 0126; 0127; 0128; 0132
(2018/11/22)
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- Manufacturing technology for fatty acyl amino acid
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The invention discloses a manufacturing technology for fatty acyl group amino acid. The invention is characterized in that fatty acid methyl ester and amino sodium are taken as raw materials, a one-step synthesis method is adopted for synthesizing N-fatty acyl amino acid sodium surfactant under the effect of a metallic oxide catalyst and the mole ratio of the raw materials fatty acid methyl ester to sodium amino acid is (1.2-1.8):(0.7-1). The raw material proportion is proper, the by-product is almost not generated, the product synthetic ratio is as high as 87% or above, the purity is high, the problems of a large amount of to-be-treated waste acid, complex operation technology, high raw material PC13 irritation, and the like, of the traditional acyl chloride process are overcome and the technology accords with the green chemical principle. The dosage of the catalyst is reasonable; the catalyst is utilized, so that the production efficiency is greatly increased in the preparation process, the production flow is shortened and the product quality is increased; the excellent product even can be directly used as a raw material in pharmacy industry.
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Paragraph 0025; 0026; 0027
(2017/12/04)
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- Control of macroscopic helicity by using the sergeants-and-soldiers principle in organogels
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The creation of well-defined homochiral helical ribbon structures in the gel phase was demonstrated. The achiral gelator 1 consists of a central aromatic group for aromatic stacking and alkylamide groups that can participate in inter-molecular hydrogen bonds and van der Waals interactions. The gelators were synthesized by simple amide coupling in moderate yields. NMR experiments were performed to obtain the evidence for π-π interaction and hydrogen-bonding interaction in organogelator 1. The solvent polarity was varied by changing the methanol and chloroform composition. The gelation behavior of the gelators was tested in various organic solvents. The SEM images of xerogels exhibited the macroscopic aggregation modes of the gelators. The CD experiments reveal that the chiral property of gelators can be reflected within the aggregates of achiral 1 without changing the helical structure derived from the aggregates of 1.
- Nam, Seong Ryong,Lee, Ho Yong,Hong, Jong-In
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supporting information; experimental part
p. 6040 - 6043
(2009/05/27)
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- Molecular mechanism of physical gelation of hydrocarbons by fatty acid amides of natural amino acids
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A variety of fatty acid amides of different naturally occurring l-amino acids have been synthesized and they are found to form gels with various hydrocarbons. The gelation properties of these compounds were studied by a number of physical methods including FTIR spectroscopy, X-ray diffraction, scanning electron microscopy, differential scanning calorimetry, rheology, and it was found that gelation depended critically on the fatty acid chain length and the nature of the amino acid. Among them l-alanine based gelators were found to be the most efficient and versatile gelators as they self-assemble into a layered structure to form the gel network. Mechanisms for the assembly and formation of gels from these molecules are discussed.
- Pal, Asish,Ghosh, Yamuna K.,Bhattacharya, Santanu
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p. 7334 - 7348
(2008/02/04)
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- GEL-STATE COMPOSITION
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A gel-state composition useful as, e.g., a composition for perfume cosmetics which is translucent to milk-white, is creamy to solid, has an excellent appearance, gives neither a tacky feeling nor a cooped-up feeling during use, and has excellent spreadability. The gel-state composition is characterized by containing at least one N-acylamino acid (A) represented by the general formula (1) and at least one oily base (B):R1-CO-X (In the formula, R1 represents a C1-25, linear or branched, saturated hydrocarbon group or an unsaturated hydrocarbon group optionally containing an aromatic ring; and X represents an aliphatic or aromatic α-, β-, or γ-amino acid.)
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- Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus
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A high throughput screen against POLO-like kinase 1 (Plk1), an anti-cancer target, identified an active extract from the fungus Arachniotus punctatus. Bioassay guided fractionation led to the isolation of the new natural product, gymnastatin N (1) and the known compound aranorosinol A (2) with IC50 values of 13 and 118 μM, respectively. A 12′-hydroxy analog of gymnastatin N, 3, was also isolated as a minor component. Gymnastatin N (1) was found to be a 52:48 mixture of (1S,6′R) and (1R,6′R) diastereomers, by synthesis of the four possible diastereomers and comparison of the optical rotation and chiral HPLC profile of each diastereoisomer with the natural product. Analogues of 1 were synthesized and evaluated against the Plk1 assay and these SAR studies suggested that the diene and free carboxylic acid moieties might be responsible for its bioactivity. Graphical Abstract.
- Phoon, Chee Wee,Somanadhan, Brinda,Heng, Sabrina Cher Hui,Ngo, Anna,Ng, Siew Bee,Butler, Mark S.,Buss, Antony D.,Sim, Mui Mui
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p. 11619 - 11628
(2007/10/03)
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- Self-assembled organogels formed by mono-chain L-alanine derivatives
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The mono-chain L-alanine derivatives self-assemble into bilayer aggregates in a number of organic liquids and gelatinize the liquids.
- Luo,Liu,Liang
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p. 1556 - 1557
(2007/10/03)
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- Synthesis of novel chiral lipophilic pyridyl-containing β-amino alcohol ligands and enantioselective hydrolysis of α-amino acid esters by chiral metallomicelles
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Seven novel chiral lipophilic pyridyl-containing β-amino alcohol ligands have been synthesized by coupling of 6-alkoxymethyl-2- chloromethylpyridine 3 with the corresponding chiral β-amino alcohols or L- cysteine. Their metal ion complexes have been inves
- You, Jingsong,Yu, Xiaoqi,Liu, Ke,Tao, Lin,Xiang, Qingxiang,Xie, Rugang
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p. 243 - 254
(2007/10/03)
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- Enantioselective hydrolysis of long chain α-amino acid esters by chiral sulfur-containing macrocyclic metallomicelles
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A novel chiral lipophilic sulfur-containing macrocyclic ligand 5 with bis-pendant alcohols in the proximity of the coordination center has been synthesized. Its metal ion complexes have been investigated as catalysts for the enantioselective hydrolysis of long chain α-amino acid esters in aqueous comicellar solution with Brij35. Large rate accelerations (up to 220 times) and moderate enantioselectivities (up to 4.85 (k(S)/k(R))) employing the macrocyclic 5-Cu2+ have been observed, whereas the acyclic 3-Cu2+ exhibits less reactivity and stereoselectivity. Taking the analogous ligand 4, lacking the hydroxy groups leads to a dramatic rate decrease, and an inversion of enantioselectivity is observed. The pKa value of the hydroxyl bound to Cu2+ is determined to be pKa=7.2 under our micellar reaction conditions.
- You, Jingsong,Yu, Xiaoqi,Li, Xingshu,Yan, Qianshun,Xie, Rugang
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p. 1197 - 1203
(2007/10/03)
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- Synthesis and antitumor activities of glycine-exchanged analogs of spicamycin
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A series of SPM VIII analogs were synthesized to investigate the effect of the amino acid moiety on the antitumor activity. The L-threonine analog and the glycylglycine analog of SPM VIII showed much higher cytotoxity to P388 murine leukemia cells (IC50 5.8 nM and 0.11 nM, respectively) than SPM VIII (IC50 25 nM). However, replacement of the glycine moiety with other amino acids greatly reduced the antitumor activity against COL-1 human colon cancer xenograft model. This study indicated that the glycine moiety of SPM VIII is crucial for the antitumor effect.
- Sakai,Kawai,Kamishohara,Odagawa,Suzuki,Uchida,Kawasaki,Tsuruo,Otake
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p. 504 - 508
(2007/10/02)
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- Dermatological compositions containing an acylamino-carboxylic acid or an alkyl ester thereof
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Topical dermatological compositions containing an acylamino-carboxylic acid compound of the formula STR1 wherein R1 is hydrogen, alkyl of 1 to 3 carbon atoms, trifluoromethyl, phenyl, halo-phenyl, nitro-phenyl or biphenylyl, R2 is hydrogen or alkyl of 1 to 3 carbon atoms, R3 is hydrogen, alkyl of 1 to 6 carbon atoms, methylthio-(alkyl of 1 to 6 carbon atoms) or benzyl, R4 is alkyl of 10 to 22 carbon atoms, n is 0, 1 or 2, R5 is alkyl of 8 to 22 carbon atoms, phenyl or biphenylyl, and R6 is hydrogen or alkyl of 1 to 3 carbon atoms; the compositions are useful for the care of the skin.
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- Process for preparing N-higher aliphatic acyl derivatives of amino acids, peptides or proteins
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A mixed acid anhydride consisting of higher fatty acid having 6 to 22 carbon atoms and sulfuric anhydride is reacted with amino acids, peptides or proteins in the presence of a base to form N-higher aliphatic acyl derivatives of amino acids, peptides or proteins respectively in good yield. The reaction mixture comprises N-acylated-amino acids, peptides or -proteins and sulfate salts and may be directly used as detergent.
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