• Title/Summary/Keyword: 1,2-Amino alcohols

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Interaction of flavins and some alcohols on the molecular level

  • Yu, Byung-Sul;Chung, Hyun-Ho;Lee, Sang-Jong;Kim, Yang-Bae;Kim, Chong-Kook
    • Archives of Pharmacal Research
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    • v.4 no.1
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    • pp.43-51
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    • 1981
  • The effect of some alcohols on the riboflavin derivatives in non-polar solvent was studied by various spectroscopic method in order to support the view point that alcohol may directly interect with the isoalloxazine moiety of FAD, the coenzyme of D-amino-acid oxidase. The most possible association complex between alcohol and riboflavin is the 1:1 complex through the 2-C carbonyl function of the isollaxazine ring nd the hydroxyl proton of alcohol. It is appeared that methanol has a larger association constant than any other alcohols, and the association constant decreases with the carbon number increases and being bulkier in the alkyl group of alcohols.

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Effects on n-Alcohols on the Amino-Proton Chemical Shifts and on the Hindered Rotation about the N-C(O) Bond of Acetamide (아세트아미드의 아미노 양성자의 화학적 이동과 N-C(O) 결합주위의 부자유회전에 미치는 n-알코올 용매 효과)

  • Gwon, Sun Gi;Choe, Jong Ho;Choe, Yeong Sang;Yun, Chang Ju;Gwon, Dae Geun
    • Journal of the Korean Chemical Society
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    • v.34 no.6
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    • pp.509-516
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    • 1990
  • 1H-nmr chemical shifts and lineshapes of amino-protons of acetamide (AA) in n-alcohols were determined. The chemical shifts are discussed by the Reichardt's solvent polarity parameter, E$_{T}$(30). The following relationship between $\delta$obs and E$_{T}$(30) was obtained. ${\delta}_{obs}$ = ${\delta}_{o}$ + aE$_{T}$ (30) + b[E$_{T}$(30)]$^2$ where ${\delta}_{o}$ is the chemical shift of the solute in gaseous state or at $E_{T}$(30) = 0, a is a characteristic constant for the protons of AA in n-alcohol solutions and b is a constant for the solute (AA)-solvent (n-alcohols) interaction. The barrier of the hindered rotation about the N-C(O) bond in AA was obtained by analysis of the lineshapes of the amino-protons in AA. The behavior of the internal rotation as well as chemical shifts of the amino-protons in AA has been found to be closely related to the $E_{T}$(30) of n-alcohols.

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Chiral Molecular Recognition by Alkoxy-amine-aluminum Derivatives (Alkoxy-amine-aluminum 유도체에 의한 키랄 분자 인식)

  • Kim, Jong-Mi
    • Journal of the Korean Society of Industry Convergence
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    • v.12 no.3
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    • pp.143-147
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    • 2009
  • The enantioselective reduction of representative prochiral alkyl-aryl ketones with a new chiral alkoxy-amine-aluminum derivatives from aluminum hydride and ${\alpha},{\alpha}$-diphenyl-${\beta}$-amino alcohols, such as (S)-(-)-2-amino-3-methyl-1,1-diphenylbutan-1-ol(AMDPB) and (S)-(-)-2-(diphenylhydroxy-methyl)pyrrolidine(DPHMP), in THF at $0^{\circ}C$ was studied. In the reduction of alkoxy-amine-aluminum derivatives, acetophenone, propiophenone, isopropiophenone, and butyrophenone are reduced to corresponding aromatic secoundary alcohols with 34~60 % enantiomeric excess of (S)-isomers. For such ketones, the optical induction was enhanced by increasing a size of alkyl groups.

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Direct Organocatalytic Regioselective α-Hydroxyamination of α-Branched Aldehydes

  • Kim, Sung-Gon;Ahn, Eun-Ju;Park, Tae-Ho
    • Bulletin of the Korean Chemical Society
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    • v.28 no.10
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    • pp.1665-1669
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    • 2007
  • A direct regioselective α-hydroxyamination of α-branched aldehydes with nitrosobenzene using cis-5-benzylproline as catalyst has been developed for the preparation of α-hydroxyamino aldehydes possessing a quaternary carbon center. Such compounds are versatile building blocks for the synthesis of quaternary α- amino acids, β-amino alcohols, and 1,2-diamines.

Synthesis and Characterization of a Hydroxylated Dendrimeric Gene Delivery Carrier

  • Kim, Tae-Il;Bai, Cheng-Zhe;Park, Jong-Sang
    • Bulletin of the Korean Chemical Society
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    • v.28 no.8
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    • pp.1317-1321
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    • 2007
  • Arginine conjugated PAMAM dendrimer, PAMAM-R was modified with propylene oxide via hydroxylation of primary amines of arginine residues. About 49 amines were detected to be converted to amino alcohols by 1H NMR. The newly synthesized polymer, PAMAM-R-PO was able to completely retard pDNA from a charge ratio of 2. The average diameter of PAMAM-R-PO polyplex was found to be 242 nm at a charge ratio of 30. The Zeta-potential value of PAMAM-R-PO polyplex was able to reach 20-30 mV over a charge ratio of 10. PAMAM-R-PO indicated higher cell viability than unmodified PAMAM-R on HeLa and 293 cells because of its hydroxylated amines. Transfection experiments on 293 cells showed that the transfection efficiency of PAMAM-R-PO was found to be 1.5-1.9 times higher than that of PEI25kDa at a charge ratio of 30. The polymer eventually displayed about 2 times greater transfection efficiency than PAMAM-R at the same charge ratio in the absence of serum. Therefore, we concluded that the modification of primary amines of PAMAMR to amino alcohols gives positive effects such as reduced cytotoxicity and enhanced transfection efficiency on 293 cells for gene delivery potency of PAMAM-R.

A Novel Synthesis of Heterocyclic Compounds Containing Coumarin Moiety of Potential Antimicrobial Activity

  • El-Fattah, M. E. Abd
    • Archives of Pharmacal Research
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    • v.21 no.6
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    • pp.723-728
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    • 1998
  • The chemical behaviours of 4-methyl-2-oxo-2H-benzopyran-7-yl oxoacetyl hydrazine (2) towards some different reagents such as anhydride compounds, aromatic aldehydes, carb on disulphide, and nitrous acid yielded the corresponding pathalazine derivatives (3, 4, 5), hydrazone derivative (6), 1,3,4-oxadiazole derivative (7, 8, 9) and acid azide (10) respectively. Treatmen of 10 with absolute alcohols, amines and ethyl amino acid ester gave the corresponding carbamate derivative (11), substituted urea derivative (12) and ethyl substituted alkyl acetate (13) respectively. The biological activity of some synthesized compounds was evaluated.

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Volatile Flavor Compounds in Low Salt-Fermented Ascidians Halocynthia roretzi Made by Flavor Enhancing (향미 개선 저식염 우렁쉥이(Halocynthia roretzi) 젓갈의 휘발성 향기성분)

  • Cha, Yong-Jun;Jeong, Eun-Jeong;Yu, Daeung
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.53 no.3
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    • pp.273-280
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    • 2020
  • Volatile compounds in fermented ascidians Halocynthia roretzi were analyzed to identify key flavor compounds using SPME/GC/MSD (solid phase microextraction/gas chromatography/mass selective detector) after 60 days of fermentation at 5℃. The control was chopped ascidians subject to anti-browning and 4% salt treatment. product A was made from product C by adding an alcohol extract of red peppers and onion peel, 0.1% of glucose, and 0.55% of mixed amino acids (MAA; 0.05% Glu, 0.1% Pro, 0.3% Ala, and 0.1% Gly). After blanching and anti-browning treatment of chopped ascidians, Product B1 was made by adding 3% anchovy sauce and 6% sorbitol. Product B2 was made by adding 0.1% glucose and 0.55% MAA to Product B1. In total, 78 compounds were identified, including 31 alcohols, 15 aldehydes, and 10 ketones. The alcohols included 12 compounds from the C8-C10 series with floral and fruit odors, including octanol, 3-methyloctanol, 2,6-dimethyl-1-heptanol, (E)-5-octen-1-ol, 6-methyloctanol, (E)-3-octen-1-ol, (E)-3-decen-1-ol, (Z)-1,5-octadien-3-ol, and nonanol. These were detected in high amounts in ascidians and all fermented products. Aldehydes (octanal, (E)-2-octenal, 2,4-heptadienal, and nonanal) and ketones (1-oten-3-one and 2-heptanone) with fatty and mushroom odors were detected as major compounds, whereas nine ethyl esters were detected only in product A.

Varying Inocula Permutations (Aspergillus oryzae and Bacillus amyloliquefaciens) affect Enzyme Activities and Metabolite Levels in Koji

  • Gil, Hye Jeong;Lee, Sunmin;Singh, Digar;Lee, Choong Hwan
    • Journal of Microbiology and Biotechnology
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    • v.28 no.12
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    • pp.1971-1981
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    • 2018
  • In this study, we investigated the altered enzymatic activities and metabolite profiles of koji fermented using varying permutations of Aspergillus oryzae and/or Bacillus amyloliquefaciens. Notably, the protease and ${\beta}$-glucosidase activities were manifold increased in co-inoculated (CO) koji samples (co-inoculation of A. oryzae and B. amyloliquefaciens). Furthermore, gas chromatography-mass spectrometry (GC-MS)-based metabolite profiling indicates that levels of amino acids, organic acids, sugars, sugar alcohols, fatty acids, nucleosides, and vitamins were distinctly higher in CO, SA (sequential inoculation of A. oryzae, followed by B. amyloliquefaciens), and SB (sequential inoculation of B. amyloliquefaciens, followed by A. oryzae). The multivariate principal component analysis (PCA) plot based on GC-MS datasets indicated a clustered pattern for MA and MB (koji samples inoculated either with A. oryzae or B. amyloliquefaciens) across PC2 (20.0%). In contrast, the CO, SA, and SB metabolite profiles displayed segregated patterns across PLS1 (22.2%) and PLS2 (21.1%) in the partial least-square discriminant analysis (PLS-DA) model. Intriguingly, the observed disparity in the levels of primary metabolites was engendered largely by higher relative levels of sugars and sugar alcohols in MA, SA, and CO koji samples, which was commensurate with the relative amylase activities in respective samples. Collectively, the present study emphasizes the utility of integrated biochemical and metabolomic approaches for achieving the optimal permutation of fermentative inocula for industrial koji preparation.