• Title/Summary/Keyword: 입체 선택성

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StereoLithography의 조형정보 생성에 관한 연구

  • 홍삼열;김준안;김인훈;양남열;이원정
    • Proceedings of the Korean Society of Precision Engineering Conference
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    • 1995.04b
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    • pp.440-444
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    • 1995
  • StereoLithography는 3차원 CAD로 작성된 모델데이타를 이용하여입체조형 실물을 빠르게 제작 하는 Rapid Prototype 기술의 한 방식으로서, 감광성 수지를 자외선 Laser 광에 의해 선택적으 로 경회시켜 원하는 한 단면형상을 이룬후 적층하는 반복작업에 의해 입체 형상을 조형하는 기법 이다. Rapid Prototype 시스템은 제품개발기간 단축과 설계완성도를 높이는 목적으로 최근 산업계에서 그 활용도가 점차 증가하는 추세에 있으며, 3차원 CAD 시스템과 함께 제품개발 체제를 통합화하고 Concurrent Engineering의 실현을 위한 주요한 Tool로써 자리를 잡아가고 있다.

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Stereoselective Synthesis of (2S,3R)-3-Hydroxyhomoserine Lactone via anti Selective Dihydroxylation of an OBO Group-Protected Vinyl Glycine Analog ((2S,3R)-3-하이드록시호모세린락톤의 입체선택적 합성 : 바이닐글라이신 OBO Ester 유도체의 입체선택적인 이중알콜화 반응)

  • Koh, Moo-hyun;Jeon, Jongho;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • v.31 no.2
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    • pp.187-192
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    • 2020
  • (2S,3R)-3-hydroxyhomoserine lactone (HSL) has been used as a key intermediate for the synthesis of various biologically active compounds. In this study, we demonstrated an efficient synthesis of HSL via anti selective dihydroxylation of a protected vinyl glycine analog with an oxabicyclo[2.2.2]octyl orthoester (OBO) ester group. Because the acyclic conformation of the substrate was efficiently controlled by the bulky OBO ester group, a diastereoselectivity of > 10 : 1 was obtained in the dihydroxylation reaction without the use of a chiral reagent. By using this result, the target compound 1 can be obtained from commercially available N-Cbz-L-serine 2 in seven steps with an overall yeid of 34%. This result could be applied to the stereoselective synthesis of biologically active molecules containing a vicinal amino diol moiety.

Stereoselective Electron-Transfer Reaction between Optical Active Cobalt(III) Complex and Racemic Cobalt(II) Complex (광학활성 코발트 (III) 착물과 라세미-코발트(II) 착물간의 입체선택적 전자전달반응)

  • Dong-Jin Lee;Maeng-Jun Jung;Myung-Ki Doh
    • Journal of the Korean Chemical Society
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    • v.35 no.5
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    • pp.500-505
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    • 1991
  • The stereoselectivity on the electron-transfer reaction between optical active ${\bigwedge}$-[CO(EDDS)]- and conformationally restricted complex $[Co({\pm}chxn)_3]^{2+}$ has been examined in aqueous solution. The products are four conformational isomers $(lel_3,\;lel_2ob,\;lelob_2,\;and\;ob_3)$ of ${\bigwedge}$-[Co(chxn)$_3]^{3+}$ with optical purities of 22% e.e, 25% e.e, 11% e.e, and 10% e.e, respectively. The reaction between ${\bigwedge}$-[CO(EDDS)]- and $[Co({\pm}chxn)_3]^{2+}$ in DMSO produced lel3-${\Delta}$ and lel2ob-${\Delta}$-[Co(chxn)$_3]^{3+}$ whose optical purities are 100% e.e, and 75% e.e, respectively.

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Stereoselective Synthesis of Novel Bestatin Analogs (새로운 베스타틴 유사체의 입체선택적 합성)

  • Seo, Youngran;Lee, SooBeom;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • v.26 no.1
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    • pp.111-115
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    • 2015
  • Two new analogs of bestatin were prepared from $\small{D}$-leucine and $\small{D}$-valine in a stereoselective and efficient way. An aminopeptidase inhibitor bestatin shows significant biological effects on immunomodulation and is marketed for the treatment of acute myelocytic leukemia. The key intermediates, trans-oxazolidine methyl esters 2a and 2b, were obtained with more than 20 to 1 stereoselectivity in a one-pot procedure by the three cascade reactions between N-hydroxymethyl protected ${\alpha}$-amino aldehydes (4a and 4b) and phenylsulfonylnitromethane ($PhSO_2CH_2NO_2$) and the following in-situ ozonolysis. Basic hydrolysis of 2a and 2b, and then the peptide coupling with $\small{L}$-Leu-OMe produced the protected derivatives of two new bestatin analogs, 3a and 3b, respectively. The new isobutyl and isopropyl analogs of bestatin (1a and 1b) were produced in overall 51% and 38% yields, respectively, with high stereoselectivity from the corresponding protected ${\alpha}$-amino aldehydes 4 in a six-step process.

Efficient Stereoselective Synthesis of (2S,3S,4S)-3,4-Dihydroxyglutamic Acid ((2S,3S,4S)-3,4-다이하이드록시글루타믹산의 효율적인 입체선택적 합성)

  • Jeon, Jongho;Shin, Nara;Lee, Jong Hyup;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • v.25 no.4
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    • pp.392-395
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    • 2014
  • (2S,3S,4S)-3,4-Dihydroxyglutamic acid (DHGA), a biologically active ${\alpha},{\beta}$-dihydroxy-${\gamma}$-amino acid, was efficiently synthesized from a readily available D-serine derivative in 30% overall yield over 11 steps. The key stereoselective $OsO_4$-catalyzed dihydroxylation reaction controlled by an N-diphenylmethylene group on the amino group of ${\gamma}$-amino-${\alpha},{\beta}$-unsaturated (Z)-ester successfully introduced the diol moiety of the intermediate 5a in 86% with more than 10 : 1 diastereomeric ration. Then it was in turn successfully converted to the desired target compound, (2S,3S,4S)-3,4-DHGA, via simple oxidation and hydrolysis in a highly stereoselective manner and a higher yield than the previous syntheses. This result strongly supports that our synthetic methodology of stereoselective $OsO_4$-catalyzed dihydroxylation should be useful in stereoselctive synthesis of various bioactive compounds with an amino diol moiety.

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.

Cloning and Molecular Characterization of Epoxide Hydrolase from Aspergillus niger LK (Apergillus niger LK 유래의 Epoxide Hydrolase 클로닝 및 특성 분석)

  • 이은열;김희숙
    • KSBB Journal
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    • v.16 no.6
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    • pp.562-567
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    • 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.

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Enantioselective Kinetic Resolution of Racemic Styrene Oxide using Recombinant Marine Fish Epoxide Hydrolase of Mugil cephalus (해양 어류 Mugil cephalus 유래의 에폭사이드 가수분해효소를 이용한 라세믹 styrene oxide의 입체선택적 분할 반응)

  • Choi, Sung Hee;Kim, Hee Sook;Lee, Eun Yeol
    • Applied Chemistry for Engineering
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    • v.19 no.5
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    • pp.491-496
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    • 2008
  • The microsomal epoxide hydrolase gene (referred to as mMCEH) of Mugil cephalus was cloned by PCR, and then inserted to pColdI and pET-21b(+) vector, respectively. The recombinant E. coli possessing the recombinant plasmids exhibited the enantioperference toward (R)-styrene oxide. When enantioselective kinetic resolutions were conducted with 20 mM racemic styrene oxide, enantiopure (S)-styrene oxide was obtained with high enantiopurity more than 99% enantiomeric excess (ee) and 24.50% yield by using the recombinant E. coli harboring pET-21b(+)/mMCEH.

Mobile Baduk-Game on the Cube (6면체 표면에서의 모바일 바둑게임)

  • Sung, Jae-Kyung;Kim, Yong-Guk
    • 한국HCI학회:학술대회논문집
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    • 2006.02a
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    • pp.830-835
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    • 2006
  • 본 연구에서는 바둑을 응용하여, 모바일에서 가능한 6면체 게임으로 구현 하였다. 기존의 바둑과 같은 룰과 비슷한 내용의 게임으로서 모바일 버튼의 단순 조작만으로 가능한 게임이다. 게임에 사용되는 6면체 바둑판과 바둑돌들은 PHOSHOP을 이용하여 3차원 모양의 객체로 생성하였다. 프로그래밍은 SKT GENX기반으로 구현하였다. 기존의 바둑판은 가로 세로 교차된19줄이 평면에 그려져 있으나, 6면체 바둑판은 한 평면에 가로 세로 5줄이 주사위 모양의 6표면에 연결되어있다. 대국 시의 모바일 화면 인터페이스는 바둑판의 6면 중 3면을 동시에 보이는 입체도와 6면을 펼친 전개도가 있다. 입체도는 모바일 버튼 조작에 의해 6면을 상하좌우 회전이 가능하도록 하였다. 입체도와 전개도는 동시에 보는 것을 기본으로 하나 사용자 선택에 의해 두 그림의 크기 위치 등이 다양하게 가능하도록 제공하고 있다. 바둑돌의 착점방식은 모바일 버튼 조작에 의해 커서의 이동으로 가능하다. 게임은 네트워크를 이용한 사람과 사람이 가능하도록 약식으로 구현하였다. 게임의 내용은 6면의 입체적 상황을 고려하면서 작전을 세워야 하므로 기존의 평면바둑에 비해 좀더 고난도의 사고와 전략을 요구하는 게임이다. 그리고 6면체 바둑게임은 모바일 스크린환경에서 기존의19줄 평면바둑이 문제시 될 수 있는 가독성과, 한 게임에 사용되는 시간에 대해서 유리한 요인으로 실용화의 가능성을 제시하고자 한다.

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