• Title/Summary/Keyword: enantioselective

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Asymmetric Ring Opening of Epoxides Catalyzed by Novel Heterobimetallic Schiff-Bases Containing Transition Metal Salts

  • Kawthekar, RahulB;Bi, Wentao;Kim, Geon-Joong
    • Bulletin of the Korean Chemical Society
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    • v.29 no.2
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    • pp.313-318
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    • 2008
  • An enantioselective ring opening of racemic terminal epoxides has been achieved by using heterobimetallic cobalt salen complexes with variety of nucleophiles. They were proven to be highly enantioselective and reactive for the synthesis of valuable chiral building blocks in enantio-riched forms up to 98% ee.

Enantioselective Synthesis of Cyclic Amino Alcohols: cis-1-Amino-2-indanol

  • Kim, Eun-Jin;An, Kyung-Mi;Ko, Soo Y.
    • Bulletin of the Korean Chemical Society
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    • v.27 no.12
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    • pp.2019-2022
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    • 2006
  • (1S,2R)-cis-1-Amino-2-indanol has been synthesized. A unique feature of the synthesis involves securing the functionalities and the configurations of the two stereocenters on an acyclic precursor before cyclizing it into the final ring-skeleton. The strategy allows both the stereocenters to be controlled in an absolute manner.

Organocatalytic Enantioselective Michael Addition of α-Nitroacetate to α,β-Unsaturated Enones: A Route to Chiral γ-Nitro Ketones and δ-Keto Esters

  • Moon, Hyoung-Wook;Kim, Dae-Young
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.291-295
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    • 2011
  • The catalytic enantioselective conjugate addition reaction of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones promoted by chiral bifunctional organocatalysts is described. The treatment of $\alpha$-nitroacetate to $\alpha,\beta$-unsaturated enones afforded the corresponding Michael adducts with high enantioselectivity. The conjugate addition adducts are easily converted to chiral $\gamma$-nitro ketones and $\delta$-keto esters.

Enantioselective Carboxylate Receptor Using Glycoluril Molecular Scaffold

  • Kim, Hyun-Gil;Kang, Jong-Min
    • Bulletin of the Korean Chemical Society
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    • v.27 no.11
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    • pp.1791-1794
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    • 2006
  • We have introduced a new enantioselective receptor 1 by incorporation of chiral building blocks to the previously reported carboxylate selective receptor 2. Binding studies carried out using $^1H$ NMR revealed that the receptor 1 showed moderate enantioselectivity with a general preference for D-amino acids and a highest enantioselectivity for leucine among the amino acids we investigated.

Characterization of PAH (Polycyclic Aromatic Hydrocarbon)-Degrading Bacteria Isolated from Commercial Gasoline (상용 휘발유로부터 분리한 다환 방향족 탄화수소(PAH) 분해 세균의 특성)

  • Kwon, Tae-Hyung;Woo, Jung-Hee;Park, Nyun-Ho;Kim, Jong-Shik
    • Korean Journal of Environmental Agriculture
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    • v.34 no.3
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    • pp.244-251
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    • 2015
  • BACKGROUND: Recent studies have described the importance of bacteria that can degrade polycyclic aromatic hydrocarbons (PAHs). Here we screened bacterial isolates from commercial gasoline for PAH degraders and characterized their ability to degrade PAHs, lipids and proteins as well as their enantioselective epoxide hydrolase activity, salt tolerance, and seawater survival. METHODS AND RESULTS: One hundred two bacteria isolates from commercial gasoline were screened for PAH degraders by adding selected PAHs on to the surface of agar plates by the sublimation method. A clear zone was found only around the colonies of PAH degraders, which accounted for 13 isolates. These were identified as belonging to Bacillus sp., Brevibacterium sp., Micrococcus sp., Corynebacterium sp., Arthrobacter sp., and Gordonia sp. based on 16S rRNA sequences. Six isolates belonging to Corynebacterium sp., 3 of Micrococcus sp., Arthrobacter sp. S49, and Gordonia sp. H37 were lipid degraders. Arthrobacter sp. S49 was the only isolate showing high proteolytic activity. Among the PAH-degrading bacteria, Arthrobacter sp. S49, Brevibacterium sp. S47, Corynebacterium sp. SK20, and Gordonia sp. H37 showed enantioselective epoxide hydrolase activity with biocatalytic resolution of racemic styrene oxide. Among these, highest enantioselective hydrolysis activity was seen in Gordonia sp. H37. An intrinsic resistance to kanamycin was observed in most of the isolates and Corynebacterium sp. SK20 showed resistance to additional antibiotics such as tetracycline, ampicillin, and penicillin. CONCLUSION: Of the 13 PAH-degraders isolated from commercial gasoline, Arthrobacter sp. S49 showed the highest lipid and protein degrading activity along with high active epoxide hydrolase activity, which was the highest in Gordonia sp. H37. Our results suggest that bacteria from commercial gasoline may have the potential to degrade PAHs, lipids, and proteins, and may possess enantioselective epoxide hydrolase activity, high salt tolerance, and growth potential in seawater.

Synthesis of Novel H8-Binaphthol-based Chiral Receptors and Their Applications in Enantioselective Recognition of 1,2-Amino alcohols and Chirality Conversion of L-Amino acids to D-Amino acids

  • Jung, Hye-In;Nandhakumar, Raju;Yoon, Hoe-Jin;Lee, Sang-Gi;Kim, Kwan-Mook
    • Bulletin of the Korean Chemical Society
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    • v.31 no.5
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    • pp.1289-1294
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    • 2010
  • Novel $H_8$-binaphthol-based chiral receptors appended with an uryl moiety (2a) and a guanidinium moiety (2b) have been designed and synthesized for the enantioselective recognition of 1,2-amino alcohols via reversible imine formation. The selectivities ($K_R/K_S$ = 9.8 ~ 19.4) of 2b in imine formation with 1,2-amino alcohols are higher than those of 2a ($K_R/K_S$ = 1.8 ~ 4.5). Similar efficiency trend have been observed in the conversion of L-amino acids to D-amino acids, i.e., the efficiency of the receptor 2b (D/L ratio: 4.3 ~ 10.1) is superior to 2a (D/L ratio: 4.0 ~ 8.7).

Assay of Epoxide Hydrolase Activity Based on PCR-linked in vitro Coupled Transcription and Translation System. (무세포 단백질합성 시스템 기반의 epoxide hydrolase 발현 및 활성 분석)

  • Lee, Ok-Kyung;Kim, Hee-Sook;Lee, Eun-Yeol
    • Journal of Life Science
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    • v.15 no.5 s.72
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    • pp.779-782
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    • 2005
  • Cell-free expression is a powerful tool for rapid protein analysis, enabling an efficient identification of gene without cumbersome procedure of transformation and cell culture. Epoxide hydrolase (EH) gene of Rhodotorula glutinis was simply amplified by PCR, and the resultant gene was expressed in vitro using a coupled Transcription/translation system. The cell-free expressed EH protein mixture exhibited the enantioselective hydrolysis activity toward (R)-styrene oxide, representing that cell-free protein synthesis system can be used for the rapid expression of an enantioselective enzyme for an efficient identification of the chiral activity.

Screening of Exiguobacterium acetylicum from Soil Samples Showing Enantioselective and Alkalotolerant Esterase Activity

  • Hwang Bum-Yeol;Kim Ji-Hyun;Kim Juhan;Kim Byung-Gee
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.10 no.4
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    • pp.367-371
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    • 2005
  • About 3,000 bacterial colonies with esterase activities were isolated from soil samples by enrichment culture and halo-size on Luria broth-tributyrin (LT) plates. The colonies were assayed for esterase activity in microtiter plates using enantiomerically pure (R)- and (S)-2-phenylbutyric acid resorufin ester (2PB-O-res) as substrates. Two enantioselective strains (JH2 and JH13) were selected by the ratio of initial rate of hydrolysis of enantiomerically pure (R)- and (S)-2-PB-O-res. When cell pellets were used, both strains showed high apparent enantioselectivity ($E_{app}>100$) for (R)-2PB-O-res and were identified as Exiguobacterium acetylicum. The JH13 strain showed high esterase activity on p-nitrophenyl acetate (pNPA), but showed low lipase activity on p-nitrophenyl palmitate (pNPP). The esterase was located in the soluble fraction of the cell extract. The crude intracellular enzyme preparation was stable at a pH range from 6.0 to 11.0.