• Biotechnology and Bioprocess Engineering:BBE
• /
• v.9 no.1
• /
• pp.62-64
• /
• 2004

The use of enantioselective hydrolysis for preparing chiral epichlorohydrins was investigated using recombinant Pichia pastoris with the enantioselective epoxide hydrolase of Rhodotorula glutinis. The rate of the recombinant epoxide hydrolase-catalyzed enantioselective hydrolysis of racemic epichlorohydrins was enhanced by the addition of 5%(v/v) Tween 20. Enantiopure (R)-epichlorohydrins with an enantiopurity of 100% ee and a yield of 26% were obtained within 5min from 50mM racemates.

• Proceedings of the Korean Society of Applied Pharmacology
• /
• 1994.04a
• /
• pp.182-182
• /
• 1994

Angiotensin converting enzyme (ACE)을 비가역적으로 불활성화시킴으로써 오랫동안 작용할 수 있는 고혈압치료제로서의 ACE억제제를 개발하기 위하여pseudomechanism-based inhibition이라는 새로운 억제기전을 가질 것으로 추정되는 아래 그림과 같은 기본 분자구조를 갖는 epoxide 유도체들을 합성하여 in vitro에서 ACE활성 억제효과를, HPLC법을 이용하여 측정하였다. 그 결과 합성되어진 epoxide 유도체들은, epoxide group대신에 sulfhydryl 또는 carboxyl group으로 치환되어져 있는 기존의 ACE 억제제들보다도 효능이 현저히 저하됨으로써, ACE의 $Zn^{2+}$ binding site와는 배위결합력이 미약하다는 것을 의미하여 준다. 또한 유도체들의 phenylring에 chloride, hydroxyl, nitro group과 같은 polar group 의 도입으로 말미암아 ACE 억제효과가 저하됨으로써 이 부위에서의 hydrophobic interaction이 ACE를 억제하는데 중요하다는 것을 시사해 주며 이외에도 이미 알려진 바와같이 carbonyl carbon과 인접한 carbon atom에 methyl group의 도입이 억제효과에 중요한 역활을 하였다. 따라서 향후에는 ACE의 $Zn^{2+}$ binding site와 강력한 배위결합을 하는 carboxyl group을 도입하고 epoxide의 위치를 변경시키며 또한 hydrophobic interaction하는 부위의 구조를 변화시켜 보다 효능이 우수한 새로운 기전의 ACE억제제를 개발해 나가고자 한다.

• Journal of Integrative Natural Science
• /
• v.3 no.2
• /
• pp.103-106
• /
• 2010

Pentiptycene and its derivatives having cavity, ${\pi}-{\pi}$ stacking prohibition, and AIEE functionalities were synthesized. 6,7-Dibromo-1,4-dihydropentiptycene-1,4-epoxide was obtained from the reaction of 6,7-dibromo-1,4-dihydronaphthalene-1,4-epoxide and anthracene. All the synthesized compounds were characterized by fourier transform infrared spectroscopy (FTIR), 1H-NMR, and 13C-NMR spectroscopy. Prepared pentiptycene derivatives could be useful precursor for organofluorene compounds which could be an excellent candidate for electronic devices such as organic light-emitting diodes (OLED's) and chemical sensor.

• Applied Chemistry for Engineering
• /
• v.18 no.3
• /
• pp.279-283
• /
• 2007

Epoxide hydrolase (EH) gene of Caulobacter crescentus was cloned by PCR and expressed in Escherichia coli. The C. crescentus EH (CcEH) primarily attacked at the benzylic carbon of (S)-styrene oxide, while the CcEH preferentially attacked at the terminal carbon of (R)-styrene oxide, thus leading to the formation of (R)-phenyl-1,2-ethanediol as the main product. (R)-phenyl-1,2-ethanediol was obtained with 85% enantiomeric excess and yield of 69% from racemic styrene oxide via enantioconvergent hydrolysis by using recombinant CcEH as the single biocatalyst.

• Journal of Life Science
• /
• v.16 no.3 s.76
• /
• pp.415-419
• /
• 2006

The epoxide hydrolase (EH) of Rhodotorula glutinis which has a high enantioselectivity against aromatic epoxide substrates was expressed to high levels in Escherichia coli based on codon usage. We analysed the Preference of codon usage between the yeast, R. glutinis, and bacteria, E. coli. E. coli, Rosetta(DE3)pLysS, harbors pRARE plasmid with tRNA genes for rare-codons was employed as a host strain. The recombinant E. coli expressing R. glutinis EH showed an enhanced enantioselective hydrolysis activity toward racemic styrene oxide. Enantiopure (S)-styrene oxide with a high enantiopurity of 99% ee (enantiomeric excess) was obtained from racemic substrates.

• KSBB Journal
• /
• v.16 no.6
• /
• pp.562-567
• /
• 2001

Aspergillus niger LK harboring the enantioselective epoxide hydrolase (EHase) activity was isolated, and enantioselectivity of EHase was tested for various racemic aromatic epoxides. The gene encoding epoxide hydrolase was cloned from cDNA library generated by reverse transcriptase-polymerase chain reaction of the isolated total mRNA. Sequence analysis showed that the cloned gene encodes 398 amino acids with a deduced molecular mass of 44.5 kDa. Database comparison of the amino acid sequence reveals that it is similar to fungal EHase, whereas the sequence identity with bacterial EHase is very low. Recombinant expression of the cloned EHase in Escherichia coli BL21 yielded an active EHases, which can offer a potential biocatalyst for the production of chiral epoxides.

• Korean Journal of Medicinal Crop Science
• /
• v.15 no.1
• /
• pp.21-25
• /
• 2007

The root of Rosa rugosa has been used in folkloric medicine as a treatment agent for diabetes. In the present study, we investigated whether (+)-catechin isolated from this plant can change the activities of hepatic drug metabolizing enzymes in rats treated with bromobenzene. Pretreatment with (+)-catechin gave no effects on the activities of aminopyrine N-demethylase and aniline hydroxylase, enzymes forming toxic bromobenzene epoxide intermediates and glutathione Stransferase, an enzyme removing toxic epoxides. However, the activity of epoxide hydrolase, an enzyme detoxifying the bromobenzene toxic intermediates was mildly recovered by (+)-catechin treatment.

• Korean Journal of Food Science and Technology
• /
• v.8 no.4
• /
• pp.219-224
• /
• 1976

The appearance of organochlorine pesticide residues in shellfish, seaweed, mud and water samples collected from south coast of Korean peninsula in September 1974 was surveyed to obtain the following results. 1) The residues in shellfish samples were found to be in the orders of Choongmoo > Yeosoo > Busan > Mokpo area, top-shell >short-necked clam > mussel > hard clam > red-shell, aldrin > ${\alpha}-BHC$ > heptachlor> ${\gamma}-BHC$ > dieldrin > heptachlor epoxide > endrin and in the range of $0-49\;{\mu}g/kg$ edible fresh muscle. 2) The residues in seaweed samples from Wando area were found to be in the orders of tangle > green laver > laver, ${\alpha}-BHC$ > ${\gamma}-BHC$ > aldrin > dieldrin > heptachlor > heptachlor epoxide > endrin and in the range of $0-60\;{\mu}g/kg$ dry matter. 3) The residues in water samples were found to be in the orders of Yeongsan River > Nakdong River > Seomjin River > Choongmoo shellfish farm, ${\alpha}-BHC$ > ${\gamma}-BHC$ > aldrin > heptachlor > dieldrin > heptachlor epoxide > endrin and in the range of $0-180\;{\mu}g/kl$ while those in mud samples were in the order of ${\alpha}-BHC$ > ${\gamma}-BHC$> aldrin > dieldrin > heptachlor > heptachlor epoxide > endrin and in the range of $0.7-18\;{\mu}g/kg$ dry matter. It should be noted that BHC contents of water samples from Yeongsan and Nakdong rivers were far above the recommended environmental levels in USA.

• Bulletin of the Korean Chemical Society
• /
• v.28 no.10
• /
• pp.1834-1836
• /
• 2007

• Proceedings of the Korean Society of Life Science Conference
• /
• 2006.09a
• /
• pp.47.2-47.2
• /
• 2006