• Title/Summary/Keyword: Amino acid ester

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Synthesis of N-Aryl Phenylglycine Ο-Alkyl Esters and Its Substitution of Ester Moiety (N-Aryl Phenylglycine Ο-Alkyl Esters의 간편한 합성 및 에스테르 치환반응)

  • 박명숙;박해선
    • YAKHAK HOEJI
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    • v.47 no.5
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    • pp.276-282
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    • 2003
  • For the development of new synthetic method for unnatural amino acid esters, N-aryl phenylglycine Ο-alkyl esters 4a∼i were synthesized through esterification, bromination, C-N bond formation from commercially available phenylacetic acids. An efficient and practical reaction condition for esters 2a∼c was that the starting materials 1a∼c were refluxed in absolute methanol for 3 hours with catalytic concentrated hydrosulfuric acid. In addition, bromines 3a∼c were formated for 3h in dichloromethane at rt with N-bromosuccinimide. Bromines 3a∼c were also converted to 4a∼i through substitution of arylamines during refluxing for 24 hours in ethanol with triethylamine. Interestingly, ethyl esters 5a∼c were formed via transesterification reaction when the p-sulfamylanilino group was used as a nucleophile in ethanol solvent.

Physicochemical Characteristics and Volatile Compounds of Glutinous Rice Wines Depending on the Milling Degrees (도정도에 따른 찹쌀발효주의 이화학적 특성 및 휘발성 향기성분)

  • Kim, Hye-Ryun;Lee, Ae-Ran;Kwon, Young-Hee;Lee, Hyang-Jeong;Jo, Sung-Jin;Kim, Jae-Ho;Ahn, Byung-Hak
    • Korean Journal of Food Science and Technology
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    • v.42 no.1
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    • pp.75-81
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    • 2010
  • In order to investigate the effects of different milling degrees on the quality of glutinous rice wines, the physicochemical properties and volatile compounds of various wines were evaluated. Sample wines prepared from glutinous rice with 90, 80, and 70% milling yields were analyzed for ethanol, pH, total acids, amino acids, soluble solids, coloring degree, UV absorbance, reducing sugars, organic acids, free sugars and volatile compounds. After fermentation for 17 days, ethanol contents in the wines ranged from 15.2 to 15.85%, while total acid levels ranged from 0.31 to 0.35%. The amino acid contents in four samples ranged from 0.63 to 0.73%, while soluble solid contents ranged from 11.4 to $13.1^{\circ}Bx$. The wine prepared from glutinous rice with a 30% degree of milling showed the highest coloring degree, UV absorbance and reducing sugar content among four samples. Furthermore, this wine had the highest levels of malic acid and acetic acid, while the glutinous rice wine prepared from rice with a 0% degree of milling had the highest levels of succinic acid and lactic acid. In all the glutinous rice wines tested, the most abundant free sugar was glucose followed by maltose. With increasing degree of milling, the alcohol, amino acid and organic acid contents of the glutinous rice wines decreased, whereas soluble solids, coloring degree, UV absorbance, reducing sugar and free sugar contents increased. Volatile compounds were identified using GC-MSD, and thirty-nine esters, seven alcohols, six acids, one aldehyde, four alkanes, one alkene and two miscellaneous compounds were identified in the glutinous rice wines. Using relative peak area, it was determined that other than ethyl alcohol, hexadecanoic acid ethyl ester was the major component and was primarily found in the range of 11.566-18.437%. Succinic acid diethyl ester and isoamyl laurate decreased with an increasing degree of milling, whereas hexanoic acid ethyl ester and 2-octenoic acid ethyl ester increased. Overall, it was shown that different milling degrees greatly affected the physicochemical and volatile characteristics of the glutinous rice wines.

Synthesis of an Octapeptide (Alanine Angiotensin) (Octapeptide (Alanine Angiotensin) 의 合成)

  • Park, Won-Kil
    • Journal of the Korean Chemical Society
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    • v.5 no.1
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    • pp.33-37
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    • 1961
  • We have shown that carboxy-peptidase destroys the biological activity of angiotensin octa-and deca-peptides. Since Proline occurs as the seventh amino acid from the amino end of the chain and since carboxypeptidase does not cleave proline from a peptid chain, it is evident that the heptapeptid H.asp-arg-val-tyr-ileu-his-pro.OH is formed by this hydrolysis. This peptide must then be biologically inactive. In order to determine whether the phenyl group of the C-terminal amino acid was the necessary requirement for biological activity of the octapeptide, $ala^8$ angiotensin octapeptide(amino acids of peptides numbered from amino end) was synthesized. For this synthesis the four dipeptides were prepared: carbobenzoxy-L-prolyl-L-alanine-P-nitrobenzyl-ester, m.p. $134-135^{\circ}C,$ carbobenzoxy-L-isoleucyl-imidazole benzyl-L-histidine methyl ester, m.p. $114-116^{\circ}C,$ carbobenzoxy-L-valyl-L-tyrosine hydrazide and carbobenzoxy B-benzyl-L-aspartyl-nitro-L-arginine. The first three dipeptides were obtained as crystalline compounds. Imidazole-benzyl-L-histidine was used in the hope that it would block the histidine imidazole against side reactions in steps subsequent to the formation of the C-terminal tetrapeptide. Also, it was through that the imidazole benzylated peptides would be easier to crystallize. This, however, was not the case. The tetrapeptide, carbobenzoxy-L-isoleucyl-L-im, benzyl-histidyl, L-prolyl-L-alanine-nitrobenzyl ester was not obtained in a crystalline form. Neither could the mono-or dihydrobromide of the tetrapeptide free base be induced to crystallize. Carbobenzoxy-L-valyl-L-tyrosine azide was condensed with the tetrapeptide free base to yield the protected hexapeptide; carbobenzoxy-L-valyl-L-tyrosyl-L-isoleucyl-L-im, benzyl, histidyl-L-Prolyl-L-alanine-nitrobenzyl ester. Upon removal of the carbobenzoxy group with hydrogen bromide in acetic acid an amorphous free base hexapeptide ester was obtained. This compound gave the correct C, H, N analysis and contained the six amino acids in the correct ratio. The octapeptide was obtained by condensing this hexapeptide with carbobenzoxy-B-benzyl-L-aspartyl-nitro, L-arginine using the mixed anhydride method of condensation. This amorphous product was proven to be homogenous by chromatography in two solvent systems and upon hydrolysis yielded the eight amino acids in correct ratio. The five protecting groups were removed from the octapeptide by hydrogenolysis over palladium black catalyst. Biological assay of the free peptide indicated that it possessed less than 0.1 per cent of both pressor and oxytocic activity of the phenylalanine8 angiotensin. This suggests that the phenyl group is a point of attachment between angiotensin and its biological receptor site.

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Synthesis of 1N-alkyl-2-amino-3-ethoxycarbonyl-pyridino [2,3-f]indole-4,9-dione derivatives (I) (1N-알킬-2-아미노-3-에톡시카르보닐-피리디노 [2,3-f]인돌-4,9-디온 유도체의 합성 (I))

  • Suh, Myung-Eun;Shin, Sung-Hee
    • YAKHAK HOEJI
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    • v.41 no.5
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    • pp.575-581
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    • 1997
  • The 6,7-dichlorquinoline-5,8-dione was reacted with ${alpha}$-cyanoacetic acid ethyl ester in ammonia solution to yield 6-(${alpha}$-cyano-${alpha}$-ethoxycarbonyhnethyl)-7-chloroquinoline- 5,8-dione (compound I). When this compound was reacted with some alkyl amines (methylamine, ethylamine, isopropylamine, etc) 2-amino-3-ethoxycarbonyl-N-alkyl-pyridino[2,3-f]indole-4,9-diones (compounds II a-e) were obtained.

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Mechanistic Investigation of Redox Process of 2-Amino-1-cyclopentene-1-dithiocarboxylate derivatives (2-Amino-1-cyclopentene-1-dithiocarboxylate 유도체들의 전극 반응메카니즘)

  • Kim, Yeong Sin;Kim, U Seong;Sim, Yun Bo;Choe, Seong Rak
    • Journal of the Korean Chemical Society
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    • v.34 no.3
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    • pp.260-266
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    • 1990
  • The electrochemical behavior of N-methyl-2-amino-l-cyclopentene-l-dithiocarboxylic acid $(N-CH_3 acdc) and 2-amino-l-cyclopentene-l-dithiomethyl ester (S-CH_3 acdc) in DMF have been investigated by the use of polarography, cyclic voltammetry and coulometry. The dimer of N-CH_3 acdc is further oxidized at +0.98 V via 2-electron process to produce free sulfur atom and cyclization product. The ring formation between two dithio group occurs along with the elimination of one sulfur atom. The elimination of sulfur atom occurs via two electron oxidation process at + 0.98 V vs. Ag/AgCl electrode. However, the cyclization does not occur in the S-CH_3$ acdc.

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Synthesis of 3-Amino-1,4-dihydropyridine Derivative via an Intramolecular Rearrangement of 1,4-Dihydropyridine-3-hydroxamate

  • Suh, Jung-Jin;Hong, You-Hwa;Bae, Myn
    • Archives of Pharmacal Research
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    • v.14 no.4
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    • pp.319-324
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    • 1991
  • 2,6-Dimethyl-4-(3'-nitrophenyl)-3-methoxylaminocarbonyl-1,4-dihydropyridine-5-carboxylic acid methylester, 3b reacted with 2-cyanoethanol or benzylalcohol to give the corresponding cyanoethylurethane compound 6c in 40.6% yield and benzylurethane compound 6d in 32% yield. The cyanoethylurethane 6c was hydrolized in ethanolic NaOH to give 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-amino-5-carboxylic acid 5-methyl ester. HCl 8 in 64.8% yield. Another acid hydrolysis of benzylurethane 6d gave 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-amino-5-carboxylic acid 5-methylester. HBr 11 in 54.7% yield.

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Approach to the Neutral Lipid and Amino Acid Components of Hirneola Auricula-Judae and Gyrophora Esculenta in Korea (한국산목이(韓國産木耳)와 석의(石衣)의 중성지질(中性脂質)과 아미노산(酸)의 성분(成分)에 관(關)한 연구(硏究))

  • Nam, Jung-Won;Ko, Young-Su
    • Journal of Nutrition and Health
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    • v.13 no.2
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    • pp.92-103
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    • 1980
  • Components of neutral lipids and amino acids of Hirneola auricula-Judae and Gyrophora esculenta grown in Korea were compared by using a Thinchrography (latroscan TH-10) and an amino acid auto analyzer(Technicon PNC-1 type), respectively. Cholesterol ester and tripalmitin were the major components among the triglycerides in both of the samples. From the total amino acids which are closely related with the nutritional valuation, aspartic acid was in the richest amount and then came with glutamic acid, serine, alanine and valine in Hirneola auricula-Judae and Gyrophora esculents contained large quantity of glutamic acid.

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Composition of Fatty Acid and Amino Acid in Water Extracted Material from Cockscomb Plant Root (맨드라미 뿌리의 물 추출물질의 지방산과 아미노산의 조성)

  • Nam, Hyun-Keun;Rho, Gi-Hwan
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.17 no.2
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    • pp.172-175
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    • 1988
  • Composition of fatty acids and amino acids in water extracted material of cooks comb plant root was studied by HPLC and GC-MS. There are 14 kinds of fatty acids in water extracted material of cockscomb plant root, especially, hexadecadienoic acid$(C_{16:2})$ was contained. Tricoasnoic acid, lignoceric acid, cerotic acid and 1,1'-[3-(2-cuclopentylethyl:dene)-1,5-pentanediyl] bis-cyclopentane were identified by HPLC and GC-MS. There are 16 kinds of acids containing ${\alpha}-aminobutyric$ acid in water extracted material of cockscomb plant root.

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Physicochemical Composition of Ramie Leaves (Boehmeria nivea L.) (모시잎의 이화학적 성분)

  • Park, Mi-Ran;Lee, Jae-Joon;Kim, Ah-Ra;Jung, Hae-Ok;Lee, Myung-Yul
    • Food Science and Preservation
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    • v.17 no.6
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    • pp.853-860
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    • 2010
  • We quantitated the major chemical components of ramie leaves (Boehmeria nivea L.) powder. The proximate compositions (all w/w) was 5.42% moisture, 28.15% crude protein, 6.95% crude fat, 15.27% crude ash, and 54.79% carbohydrate, respectively. The total, insoluble, and soluble dietary fiber contents were $39.66{\pm}1.84g/100g$, $20.32{\pm}2.02g/100g$, and $19.34{\pm}2.84g/100g$, respectively. The major free sugars were glucose, galactose and lactose. Seventeen amino acids were isolated. Essential amino acids constituted 44.65% of the total. When free amino acid levels were evaluated, 25 kinds of components were detected, of which 18.15% were essential. Only caproic acid methyl ester and pentadecanoic acid were detected when fatty acid examined. The contents of vitamin A, vitamin E and vitamin C were 0.0194 mg%, 0.0184 mg%, and 0.1833 mg%, respectively. The mineral contents of were in order of Cu

Studies on the Michael Addition Reaction between Secondary Amino Groups on the Silica Surface with Poly(ethylene glycol) Diacrylates (실리카 나노입자 표면에 결합된 2차 아미노기와 Poly(ethylene glycol) Diacrylate의 마이클 부가반응에 대한 연구)

  • Jeon, Ha Na;Ha, KiRyong
    • Polymer(Korea)
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    • v.36 no.6
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    • pp.822-830
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    • 2012
  • We used dipodal type bis[3-(trimethoxysilyl)propyl]amine (BTMA) silane coupling agent to modify silica nanoparticles to introduce secondary amino groups on the silica surface. These N-H groups were reacted with three different molecular weights (M.W. = 258, 575, and 700) of poly(ethylene glycol) diacrylates to introduce different attached layer thicknesses on the silica surface by Michael addition reaction. After Michael addition reaction, we used several analytical techniques such as fourier transform infrared spectroscopy (FTIR), elemental analysis (EA) and solid state $^{13}C$ cross-polarization magic angle spinning (CP/MAS) nuclear magnetic resonance spectroscopy to characterize introduced structures. We found almost complete Michael addition reaction of both two acrylate groups of PDGDA with N-H groups of BTMA modified silica to form ${\beta}$-amino acid esters. Between equimolar ratio of pure BTMA and pure PEGDA reaction, only one acrylate group of two acrylate groups of PEGDA reacted with N-H groups of pure BTMA to form ${\beta}$-amino acid ester and the other remaining acrylate group can be used to form a polymer later.