• Title/Summary/Keyword: Diol

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Cyclohexanol Dehydrogenase isozymes produced by Rhodococcus sp. TK6 (Rhodococcus sp. TK6가 생산하는 Cyclohexanol Dehydrogenase의 동위효소)

  • 김태강;이인구
    • Microbiology and Biotechnology Letters
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    • v.27 no.2
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    • pp.124-128
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    • 1999
  • TK6 was able to produce NAD+ dependent cyclohexanol dehydrogenase(CDH). The production of CDH was increased rapidly at the logarithmic phase and maintained constantly after that. In order to investigate the inductive production of CDH by various substrates, the bacteria were grown in the media containing alicyclic hydrocarbons and various alcohols as a sole crabon souce. CDH was induced most actively by cyclohexanol. Cyclohexanone and cyclohexane-1,2-diol also induced remarkable amount of CDH but it was induced weakly by 1-propanol, 1-butanol, 1-pentanol, 1-hexanol, 2-propanol, and 2-methyl-1-propanol. The dehydrogenase of the bacteria grown in the media containing cyclohexanol were weakly active for various alcohols, but the dehydrogenase activity for cyclohexane-1,2-diol was twice as much as that for cyclohexanol. Activity staining on PAGE of the cell free extract of Rhodococcus sp. TK6 grown in the media containing cyclohexanol reveals at least sever isozyme bands of CDH and we nominated the four major activity bands as CDH I, II, III, and IV. CDH I was strongly induced by cyclohexanol, cyclohexane-1,2-diok, but its activity was specific to cyclohexane-1,2-diol and 1-pentanol. CDH IV was strongly induced by cyclohexanol and cyclohexane-1,2-diol, and its activity was very specific to cyclohexane-1,2-diol.

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Induction of Electrophilic Metabolites of PAH by Placental Microsomes in Mice (쥐의 태반조직에 의한 PAH 화합물의 대사활성화)

  • 김선희;조철오;신대현;박균하
    • The Korean Journal of Zoology
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    • v.31 no.2
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    • pp.142-146
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    • 1988
  • Metabolism of benzo(a)pyrene, the most thoroughly studied PAH, was studied in mouse placental microsomes incubated with $^3$H-labeled B(a)P. B(a)P metabolites were separated using HPLC fitted with a C18- $\mu$ Bondapak column. The single major metabolite by mouse placental microsomes induced by B(a)P was 7, 8-diol B(a)P, while 4, 5-diol B(a)P, 3-OH and quinones constituted minor metabolites. Treatment with 3-methyl-cholanthrene to mice resulted in indudion of hydroxy B(a)P and quinone compounds. Phenobarbital treated mouse placental microsomes also showed elevated level of B(a)P metabolism with 7, 8-diol B(a)P as a major metabolite.

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Effect of Different GC Columns on the Quantitative Analysis of Long Chain Alkyl Diols (LCDs) (특성이 다른 GC 컬럼이 long chain alkyl diols (LCDs)의 정량 분석에 미치는 영향)

  • GAL, JONG-KU;KIM, JUNG-HYUN;NAM, SEUNG-IL;SHIN, KYUNG-HOON
    • The Sea:JOURNAL OF THE KOREAN SOCIETY OF OCEANOGRAPHY
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    • v.22 no.2
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    • pp.45-55
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    • 2017
  • Long chain alkyl diols (LCDs) have been reported in sediments from various marine environments. Rampen et al. (2012) introduced the paleo-sea surface temperature (SST) proxy, Long chain Diol Index (LDI) based on the relative abundance of $C_{30}$ 1,15-diol, $C_{28}$ 1,13-diol, and $C_{30}$ 1,13-diol. In general, CP-Sil5CB and DB-5ms columns have been used for the quantitative and qualitative analysis of LCDs with a GC-MS. In this study, we examined the effect of three different columns (CP-Sil5CB, HP-5ms and DB-5) on the quantitative analysis of LCDs using marine sediments from the East Sea of Korea and the western Arctic Ocean. In general, our study showed that the results of CP-Sil5CB differed significantly from those of HP-5ms and DB-5. However, the differences of the LDI-derived SSTs among three columns were $0.1-0.2^{\circ}C$ for the East Sea and $0.2-0.7^{\circ}C$ for the western Arctic Ocean, which were well within the calibration error range (${\pm}1{\sigma}$). Accordingly, our study showed that the use of different columns resulted in significant differences of LCDs concentrations, but its effect on the LDI was relatively insignificant. Therefore, it appears that the different columns can be used for the paleo-SST reconstruction in the East Sea and the western Arctic Ocean using the LDI proxy.

Full-atomistic simulations of poly(ϵ-caprolactone) diol models with CVFF and CGenFF

  • Chang, Yin;Chang, Shu-Wei
    • Multiscale and Multiphysics Mechanics
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    • v.1 no.4
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    • pp.327-340
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    • 2016
  • Poly(${\epsilon}$-caprolactone) (PCL) diol, with good biodegradation and biocompatibility, is one of the widely used soft segments (SSs) in composing bio-polyester-urethanes (Bio-PUs), which show great potential in both biomedical and tissue engineering applications. Properties of Bio-PUs are tunable by combining SS monomers with different molecular weights, structures, modifications, and ratio of components. Although numbers of research have reported many Bio-PUs properties, few studies have been done at the molecular scale. In this study, we use molecular dynamic (MD) simulation to construct atomistic models for two commonly used PCL diol SSs with different molecular weights 1247.58 Da and 1932.42 Da. We compare the simulation results by using two widely used classical force fields for organic molecules: Consistent Valence Force Field (CVFF) and CHARMM General Force Field (CGenFF), and discuss the validity and accuracy. Melt density, volume, polymer conformations, transition temperature, and mechanical properties of PCL diols are calculated and compared with experiments. Our results show that both force fields provide accurate predictions on the properties of PCL diol system at the molecular scale and could help the design of future Bio-PUs.

Steroid compounds from the marine sponge Raspilia hirsute

  • Rho Jung-Rae
    • Journal of the Korean Magnetic Resonance Society
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    • v.10 no.1
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    • pp.89-95
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    • 2006
  • The methanolic extract of the marine sponge Raspilia hirsute collected from Keomun Island resulted in three types of sterols: a mixture of (24S)-Poriferasta-5, 25-diene-$3\beta$, 24-diol and (24R)-Stigmasta-5, 25-diene-$3\beta$, 24 -diol (1), 25,26,27-Trinorcholest-5-en-$3\beta$,24-diol (2), and Pregn-5-en-20-on-$3\beta$-ol (3). The isolation and structural determination of these sterols are reported here. Compound 1 showed moderate cytotoxicity against human Leukemia cell line K562.

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Burkholderia cepacia Strain G4 (pHG-2) Accumulates cis-3-Methyl-3,5-cyclohexadien-1,2-diol While Growing on Toluene

  • Hur, Hor-Gil
    • Journal of Applied Biological Chemistry
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    • v.43 no.1
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    • pp.44-48
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    • 2000
  • Burkholderia cepacia strain G4 (pHG-2) containing toluene 2-monooxygenase and toluene dioxygenase, was able to grow on toluene and accumulate cis-3-methyl-3,5-cyclohexadien-1,2-diol (cis-toluene dihydrodiol) in the liquid culture. The cis-toluene dihydrodiol produced was identical to the authentic compound, as judged through mass spectrometry and nuclear magnetic resonance analysis. Our results indicate that pHG-2 provides an economical means to produce chemically-important chiral synthons while growing on toluene.

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Cytotoxic Activity of 13(E)-Labd-13-ene-8$\alpha$, 15-diol

  • Lim Jin A;Kwang Jung Sook;Yu Byung Soo;Baek Seung Hwa
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.18 no.4
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    • pp.1169-1172
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    • 2004
  • The cytotoxic activity of 13(E)-labd-13-ene-8α, 15-diol (1) was evaluated against tumor cell lines. A comparison of IC/sub 50/ values of this compound in cancer cell lines showed that their susceptibility to this compound decreased in the following order: P388>B16{F10>MDA-MB-231>A549>KB>SNU-C4 by the MTT method. 13(E}-Labd-13-ene-8α, 15-diol (1) was the most effective growth inhibitor of P388 murine leukaemia cell lines, producing approximately 8.3㎍/mL of IC/sub 50/ in the MTT method.

Purification and Characterization of a Cyclohexanol Dehydrogenase from Rhodococcus sp. TK6

  • Kim, Tae-Kang;Choi, Jun-Ho;Rhee, In-Koo
    • Journal of Microbiology and Biotechnology
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    • v.12 no.1
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    • pp.39-45
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    • 2002
  • Activity staining on the native polyacrylamide gel electrophoresis (PAGE) of a cell-free extract of Rhodococcus sp. TK6, grown in media containing alcohols as the carbon source, revealed at least seven isozyme bands, which were identified as alcohol dehydrogenases that oxidize cyclohexanol to cyclohexanone. Among the alcohol dehydrogenases, cyclohexanol dehydrogenase II (CDH II), which is the major enzyme involved in the oxidation of cyclohexanol, was purified to homogeneity. The molecular mass of the CDH II was determined to be 60 kDa by gel filtration, while the molecular mass of each subunit was estimated to be 28 kDa by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE). The CDH II was unstable in acidic and basic pHs, and rapidly inactivated at temperatures above $40^{\circ}C$ . The CDH II activity was enhanced by the addition of divalent metal ions, like $Ba^2+\;and\;Mg^{2+}$. The purified enzyme catalyzed the oxidation of a broad range of alcohols, including cyclohexanol, trans-cyclohexane-1,2-diol, trans-cyclopentane-l,2-diol, cyclopentanol, and hexane-1,2-diol. The $K_m$ values of the CDH II for cyclohexanol, trans-cyclohexane-l,2-diol, cyclopentanol, trans-cyclopentane-l,2-diol, and hexane-l,2-diol were 1.7, 2.8, 14.2, 13.7, and 13.5 mM, respectively. The CDH II would appear to be a major alcohol dehydrogenase for the oxidation of cyclohexanol. The N-terminal sequence of the CDH II was determined to be TVAHVTGAARGIGRA. Furthermore, based on a comparison of the determined sequence with other short chain alcohol dehydrogenases, the purified CDH II was suggested to be a new enzyme.

Conjugation of Cyclohexane Metabolite in Liver Damaged Rats

  • Joh, Hyun-Sung;Yoon, Chong-Guk
    • Biomedical Science Letters
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    • v.12 no.4
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    • pp.361-370
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    • 2006
  • To evaluate an effect of pathological liver damage on the conjugation of cyclohexane metabolites, rats were pretreated with 50% $CCl_4$ dissolved in olive oil (0.1 ml/100 g body weight) 10 or 17 times intraperitoneally at intervals of every other day. On the basis of liver function, the animals pretreated with $CCl_4$ 10 times were identified as acutely liver damaged ones and the animals pretreated with $CCl_4$ 17 times were identified as severly liver damaged ones. To these liver damaged animals, cyclohexane (a single dose of 1.56 g/kg body weight, i.p.) was administered at 48 hr after the last injection of $CCl_4$. The rats were sacrificed at 4 or 8 hr after injection of cyclohexane. The cyclohexane metabolites, cyclohexanol (CH-ol), cyclohexane-1,2-diol (CH-1,2-diol), cyclohexane-1,4-diol (CH-1,4-diol), and their glucuronyl conjugates and cyclohexanone were detected in the urine of cyclohexane treated rats. The urinary concentration of cyclohexane metabolites was generally more increased in liver damaged animals than normal ones, and the increasing rate was higher in $CCl_4$ 17 times injected rats than 10 times injected ones. And liver damaged.ats, especially $CCl_4$ 17 times treated ones, had an enhanced ability of glucuronyl conjugation to CH-ol analogues compared with normal group. Futhermore, CH-1,2 and 1,4-diol were all conjugated with glucuronic acid in $CCl_4$ 17 times injected animals. On the other hand, the increasing rate of activities of hepatic cytochrome P450 dependent aniline hydroxylase, alcohol dehydrogenase and urine diphosphate glucuronyl transferase was higher in 17 times $CCl_4$-treated rats compared with normal and $CCl_4$ 10 times injected animals. Taken all together, it is assumed that an increased urinary excretion amount of cyclohexane metabolites in liver damaged rats might be caused by an increase in the activities of cyclohexane metabolizing enzymes. And enhanced conjugating ability of CH-ol in liver damaged animals and novel finding of conjugating form of CH-1,2 and 1,4-diol might be caused by increase in the activity of hepatic diphosphouridine glucuronyltransferase.

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Enantioconvergent Hydrolysis of Racemic Epoxides for Production of Enantiopure Epoxides and Vicinal Diols using Epoxide Hydrolases (에폭사이드 가수분해효소에 의한 광학수렴반응을 이용한 광학활성 에폭사이드 및 Vicinal Diol 제조)

  • Lee, Eun-Yeol
    • KSBB Journal
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    • v.22 no.3
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    • pp.123-128
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    • 2007
  • One drawback of conventional kinetic resolution of racemic epoxides by epoxide hydrolase (EH) is that the theoretical yield can never exceed 50%. This 50% limitation can be overcome by using enantioconvergent process, in which both enantiomers of the racemic epoxide are transformed via stereochemically matching pathways into a single enantiopure diol as the sole product in 100% theoretical yield. In order to make a single enantiopure vicinal diol, the two enantiomers of the racemic epoxide must be hydrolyzed with retention and inversion of configuration each other. The EHs should be enantio- and regiospecific at the same time. The enantioconvergent hydrolysis with EHs and relevant biotransformation for preparing enantiopure epoxides and vicinal diols with a high yield are reviewed.