• Korean Journal of Food Science and Technology
• /
• v.29 no.3
• /
• pp.446-451
• /
• 1997

The primary alcohol groups of four kinds of polysaccharides (com starch, rice starch, sweet potato starch, and cellulose), with different structures and water solubilities, were oxidized to carboxyl groups using 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion (TEMPO) at $25^{\circ}C$. The optimum pH, TEMPO content, and NaBr content for the TEMPO/hypobromite-catalyzed oxidation of the polysaccharides were $10.5{\sim}11.0$, 10 mmol/mol primary alcohol, and 0.49 mmol/mol primary alcohol, respectively. The oxidation degree for the primary alcohol group was more than 90% for all four kinds of the polysaccharides. The oxidation process greatly increased the water solubility of the polysaccharides. Water-insoluble polysaccharide such as cellulose became water-soluble to the extent of 8.42% (w/v). And also, the polysaccharides with very low water solubility (less than 0.10% (w/v)) such as com starch, rice starch, and sweet potato starch had high water solubility of approximately 45%(w/v). The gel-forming abilities with calcium ion were determined. The oxidized polysaccharides are new anionic polymers with unique structures that could have application as gums, gels, and films.

• Journal of Convergence for Information Technology
• /
• v.11 no.9
• /
• pp.109-114
• /
• 2021

Cr(VI)-quinoline compound[(C₉H₇NH)₂Cr₂O₇] was synthesized by the reaction between of quinoline and chromium(VI) trioxide, and structure was FT-IR, elemental analysis. The oxidation ability of benzyl alcohol greatly depends upon the dielectric constant of the used organic solvent, where carbon tetrachloride was worst and N,N'-dimethylformamide was best solvent. Noticeably, in N,N'-dimethylformamide solvent, Cr(VI)-quinoline compound oxidized substituted benzyl alcohols. The Hammett reaction constant(ρ)=-0.69(303K). As a resuit, Cr(VI)-quinoline compound was found as efficicent oxidizing agent that converted benzyl alcohol, allyl alcohol, primary alcohol and secondary alcohols to the corresponding aldehydes or ketones. Cr(VI)-quinoline compound was selective oxidizing agent of benzyl alcohol, allyl alcohol and primary alcohol in the presence of secondary alcohol ones.

• Korean Journal of Food Science and Technology
• /
• v.33 no.1
• /
• pp.40-44
• /
• 2001

The effects of TEMPO and NaBr concentration, and temperature on the selective oxidation of primary alcohol groups in corn starch were examined. Reaction time decreased with the increased levels of TEMPO, NaBr and temperature up to 1.7 mM and 100 mM per 100 mM anhydroglucose unit(AGU) and $14^{\circ}C$, respectively, and did not change appreciably at the higher levels. Yield decreased with the increased NaBr levels and was not affected TEMPO level and the temperature. NaBr level and temperature showed negative effects on the selectivity. But the selectivity was not affected by NaBr level and temperature until 100 mM/100 mM AGU and $6^{\circ}C$. TEMPO had no effect on the selectivity significantly.

• The Journal of the Convergence on Culture Technology
• /
• v.8 no.6
• /
• pp.927-933
• /
• 2022

We synthesized (C₁₀H₈N₂H)₂Cr₂O₇, The structure of the product was characterized with FT-IR(infrared) and elemental analysis. The oxidation of benzyl alcohol by (C₁₀H₈N₂H)₂Cr₂O₇ in organic solvents showed that the reactivity increased with the increase of the dielectric constant. The oxidation of alcohols was examined by (C₁₀H₈N₂H)₂Cr₂O₇ in DMF, acetone. As a resuit, (C₁₀H₈N₂H)₂Cr₂O₇ was found as efficicent oxidizing agent that converted benzyl alcohol, allyl alcohol, primary alcohol and secondary alcohols to the corresponding aldehydes or ketones(65%~95%). The selective oxidation of alcohols was also examined by (C₁₀H₈N₂H)₂Cr₂O₇ in DMF, acetone. (C₁₀H₈N₂H)₂Cr₂O₇ was selective oxidizing agent(15%~95%) of benzyl alcohol, allyl alcohol and primary alcohol in the presence of secondary ones. In the presence of DMF solvent with acidic catalyst such as H₂SO₄. (C₁₀H₈N₂H)₂Cr₂O₇ oxidized benzyl alcohol(H) and its derivatives. The Hammett reaction constant(ρ) was -0.69(308K). The observed experimental data were used to rationalize the hydride ion transfer in the rate determining step.

• Journal of the Korea Academia-Industrial cooperation Society
• /
• v.19 no.8
• /
• pp.378-384
• /
• 2018

$C_9H_7NHCrO_3Cl$ was synthesized by reacting $C_9H_7NH$ with chromium (VI) trioxide. The structure of the product was characterized by FT-IR (Fourier transform infrared) spectroscopy and elemental analysis. The oxidation of benzyl alcohol by $C_9H_7NHCrO_3Cl$ in various solvents showed that the reactivity increased with increasing dielectric constant(${\varepsilon}$) in the following order: DMF (N,N'-dimethylformamide) > acetone > chloroform > cyclohexane. The oxidation of alcohols was examined by $C_9H_7NHCrO_3Cl$ in DMF. As a result, $C_9H_7NHCrO_3Cl$ was found to be an efficient oxidizing agent that converts benzyl alcohol, allyl alcohol, primary alcohols, and secondary alcohols to the corresponding aldehydes or ketones (75%-95%). The selective oxidation of alcohols was also examined by $C_9H_7NHCrO_3Cl$ in DMF. $C_9H_7NHCrO_3Cl$ was the selective oxidizing agent of benzyl, allyl and primary alcohol in the presence of secondary ones. In the presence of DMF with an acidic catalyst, such as $H_2SO_4$, $C_9H_7NHCrO_3Cl$ oxidized benzyl alcohol (H) and its derivatives ($p-OCH_3$, $m-CH_3$, $m-OCH_3$, m-Cl, and $m-NO_2$). Electron donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. The Hammett reaction constant (${\rho}$) was -0.69 (308K). The observed experimental data were used to rationalize hydride ion transfer in the rate-determining step.

• Korean Journal of Microbiology
• /
• v.32 no.2
• /
• pp.172-175
• /
• 1994

Xanthomonas campestris M12 carrying OCT plasmid which could dissimilate octane was able to utilize n-alkanes of eight to sixteen carbon atoms via the capacity of this plasmid. M12 strain could utilize terminal oxidation products of these primary, alkanes, alcohols, aldehydes and fatty acids but not hexanoic acid, adipic acid, pimelic acid and heptanal. This strain also biodegraded n-alkanes by monoterminal or diterminal oxdation of straight-chain fatty acids, and branched-chain alkane.

• Journal of the Korean Chemical Society
• /
• v.31 no.4
• /
• pp.359-363
• /
• 1987

Sonic waves (50KHz) was accelerated the oxidation reaction of primary, benzyl and secondary alcohol with $BaMnO_4\;and\;KMnO_4-CuSO_4{\cdot}5H_2O$ to give the corresponding aldehyde and ketone at $30^{\circ}C/1$ atm. in high yields compared to stirring or refluxing condition.

• Korean Journal of Food Science and Technology
• /
• v.32 no.1
• /
• pp.147-153
• /
• 2000

We could produce algin-like biomaterial of polyiduronan using polyglucuronic acid C5-epimerase with polyglucuronic acid prepared by specific oxidation of primary alcohol groups of four kinds of polysaccharides(corn starch, rice starch, sweet potato starch, and cellulose). The enzyme activity was determined by the modified Dische carbazole methodology with the isolated crude enzyme from the supernatant centrifuged at $100,000{\times}g$ for 1 hr after grinding fresh bovine liver. And then, the optimal substrate, pH, and temperature for the enzyme reaction of polyglucuronic acid C5-epimerase were determined as the oxidized sweet potato starch, 7.0, and $30^{\circ}C$, respectively. Conclusively, it could be possible to epimerize polyglucuronic acid in the oxidized sweet potato starch to polyiduronic acid. Therefore, we could obtain algin-like polysaccharide using the oxidized sweet potato starch and polyglucuronic acid C5-epimerase isolated from bovine liver.

• Proceedings of the Korean Society of Applied Pharmacology
• /
• 1994.04a
• /
• pp.222-222
• /
• 1994

목적하는 화합물인 2',5'-dihydroxy-3'-무치환 유도체(1)는 uridine을 sodium metaperiodate로 산화하여 dialdehyde를 얻은다음 1,2-dianilinoethane으로 3'-aldehyde만을 선택적으로 보호, 2'-aldehyde를 NaBH$_4$로 환원, alcohol로 하여 deprotection 하므로서 hemiacetal율 얻는다. 이 hemiacetal을 TsSNHHNH$_2$로 처리하여 목적하는(1) 화합물을 얻었으며 2-azido-5-Hydroxy-3'-무치환 유도체(2)는 (1)화합물 합성시 얻은 hemiactal을 출발 물질로 하여 먼저 TBDPSCl로 silyaltion하여 5'-hydroxyl group을 보호하고 TsNHNH$_2$로 3'-위치를 hydrazone으로 한다음 NaB(CNH$_3$로 처리하여 얻은 hydrazide를 NaOAc를 반응시켜 2'-hydroxy-3'-무치환-5'-silyl 유도체를 얻고 또한 2',3'-dihydroxy group을 tosyl화, azido화, 5'-silyl group을 deprotection 하므로서 (2)를 얻었다. 또한 2',3'-dihydroxy-5'-무치환 유도체(4)는 uridine의 2',3'-위치를 먼저 protection, 5'-위치를 benzoyl화 2',3'-deprotection, periodate oxidation하여 얻은 diol을 silyl화 한 다음 5'-위치를 benzoyl화, 2',3'-deprotection, 산화하여 얻은 hemiacetal의 silyl group을 제거한후 primary hydroxyl group만을 선택적으로 silyl화, TsNHNH$_2$, NaB(CN)H$_3$ 및 NaOAc로 처리하므로서 얻은 2'-hydroxy-3'-0-silyl group-5'-무치환 화합물을 tosyl, azido화 한다음 desilylation하여 얻었다. 목적하는(1) 화합물의 diasteromer 인 2',3'-dihydroxy-5'-무치환 유도체(3)는 (4)화합물 합성시 얻은 hemiactal을 key intermediate로 하여 TsNHNH$_2$, NaB(CN)H$_3$ 및 NaOAc로 처리하므로서 얻을수 있었다. 이들 화합물들의 각종 DNA 및 RNA virus에 대한 항 바이러스작용을 검토한 결과 현저한 항 바이러스 작용을 나타내지 않았다.

• Korean Journal of Food Science and Technology
• /
• v.33 no.2
• /
• pp.209-215
• /
• 2001

This study was conducted to examine the effects of 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion(TEMPO) and sodium bromide(NaBr) for the selective oxidation on primary alcohol groups of rice starch molecules in rice flour and to use oxidized rice flour in Julpyun to extend its shelf life. Reaction time decreased with higher levels of TEMPO and NaBr. Yield and selectivity decreased with increased NaBr levels. TEMPO increased yield until certain levels, but decreased thereafter. The levels of TEMPO and NaBr for the preparation of oxidized rice flour were determined as 0.9 and 44 mM/100 mM anhydroglucose unit, respectively. Water and oil binding capacities, and viscosity increased significantly by the oxidation of rice flour. The partial replacement of rice flour with oxidized rice flour increased peak viscosity and decreased setback. Oxidized rice flour with the increased amount of water showed positive effect on the textural properties of Julpyun during storage.