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DNA-Transfection을 위한 양이온성 리포좀에 포함되는 Phytosphingosine 유도체의 개발
남궁성건,박선이 서울여자대학교 자연과학연구소 2001 자연과학연구논문집 Vol.13 No.-
본 연구에서 합성한 TMPㆍI를 함유하는 양이온성 리포좀(TMPㆍI : DOPE = 1 : 1(무게비))으로 in vitro 계에서 유전자 전달 실험을 수행한 결과, L/D 비가 증가할수록 유전자 전달 정도가향상되었고 TMPㆍI는 리포좀 종류에 따라 유전자 전달 정도의 차이를 나타냈는데 SUV 보다 MLV일 때 그 효율이 1 5배 더 증가하였다. DOPE/phytoS(1 : 1 무게비)로 구성된 대조 리포좀의 유전자 전달 효율은 L/D 비가 20에서도3% 정도에 불과한데 비하여 phytos의 아민기에트리메틸레이션한 TMPㆍI를 함유하는 양이온성 리포좀은 11%로 유전자 전달 효율을 3 ~4배 정도 증가시킴을 확인할 수 있었다. 또한 기초적인 생물학적 테스트를 통하여 TMPㆍI를 포함하는 양이온성 리포좀은 TMS를 포함하는 리포좀보다 훨씬 뛰어난 암 전이 억제 효파 및 성장 억제 기능도 나타냄을 알 수 있었다. N,N,N-Trimethylphytosphingosinium iodide (TMPㆍI), a derivative of phytosphingosine(PhytoS), contained in cationic liposome was used to examine its DNA transfection efficiency in BHK cell line in vitro. The result in DNA transfection assay showed that DOPE/TMP liposome was more effective than the control group, DOPE/PhytoS. Unlike conventional liposomes, the liposome comprising TMPㆍI exhibited a high DNA transfection efficiency and it will be very useful tool in developing the delivery system of gene with antitumor activity.
Phytosphingosine의 protection 화학 및 이 유도체들의 반응성에 관한 연구
장소현,남궁성건 서울여자대학교 2010 자연과학연구논문집 Vol.22 No.-
To develop synthetic routes for the target molecule, (2S,3R,4R)-2-aminooctadecane-1,3,4-triol (1), three kinds of syntheses for key intermediates (2a), (4) and (5) were explored from phytosphigosine through several protection processes. The first approach was proceeded by the reaction of oxazoline (2) with acetone, producing bicyclic compound (3) in 70% yield, instead of acetal (2a). Formation of the compound (3) was unavoidable in Lewis acid-induced acetal protection reactions, as a major product. The second key intermediate (4) was prepared from the reaction of oxazoline (2) with CH2Br2 under basic phase transfer reaction condition in 60% yield. Methylene acetal (4) was not reactive with strong bases so that it was not converted into the desired isomer (4a) at all. Finally, synthesis of another key intermediates (5) was successfully achieved by the reaction of oxazoline (2) with diethyl carbonate in 83% yield. The lithium hexamethyldisilazide (LHMDS)-promoted reaction of carbonate (5) only gave tricyclic compound (6) in 83% yield, without formation of the precursor (5a). The proposed formation mechanism for compound (6) is described.
폴리펩타이드로 구성된 새로운 키랄,거대고리 상 이동 촉매의 합성에 관한 연구
남궁성건,고윤주 서울여자대학교 자연과학연구소 2000 자연과학연구논문집 Vol.12 No.-
We designed the chiral, macrocyclic phase transfer catalyst (3) mixed with both chemical characters of catalyst (1) and preorganized conformation of receptor (2a-b). It may be the more efficient catalyst in the sense of structural features relative to compound (1) and (2a-b). It was necessary that the standard compound (4) similar to the structure of compound (3) was synthesized to confirm the stability and solubility of quaternary ammonium salt (3). The compound (4) was obtained from 3,5-pyridinedicarboxylic acid through 6 steps in overall 35% yields according to scheme 1. The chemical properties of compound (4) were satisfied in various phase transfer reactions. The synthesis of compound (3) has been attempted according to scheme 2. At present, precursor (3a) was produced from 3,5-pyridinedicarboxylic acid through 21 steps in overall 1.9% yields. The compound (3) that can be obtained by sample alkylation of the precursor (3a) will be applied to various phase transfer catalyses requiring asymmetric induction or kinetic resolution.
(3R,4R)-Epoxyphytosphingosine 유도체의 합성에 관한 연구
남궁성건,이선희 서울여자대학교 자연과학연구소 2007 자연과학연구논문집 Vol.19 No.-
As an key intermediate for the synthesis of (2S,3S)-2-Amino-1,3-octadecanediol (safingol), the derivative of (3R,4R)-epoxyphytosphingosine (6) was prepared from D-phytosphingosine through two step reactions in 46% overall yield. The diol (5) was regioselectively produced by single step protection reaction on both C-l and C-2 amino alcohol functionalities of D-phytosphingosine in 85% yield. A mixture of the desired epoxide (6) and the other diastereomer (7) were initially obtained from the diol (5) in single step epoxidation reaction. Their optimum ratio was 5 : 1, generating the compound (6) as a major product in 54% yield. Its purification was efficiently achieved by column chromatographic separation method (chloroform : ethyl acetate, 10 : 1). Regioselective ring-opening reaction for the epoxide (6) at C-4 position with LiAlH₄ generally gave the inseparable mixture of precursors (8) and (9) with a rado of 1 : 2 in 65% yield. Other most reducing agents were inactive to produce them. The typical deprotection reactions of those precursors with strong acid and base will result in formation of safingol.
남궁성건,이경하 서울여자대학교 자연과학연구소 2005 자연과학연구논문집 Vol.17 No.-
To develope new types of red emitters, the target molecules (1-3) were designed through structural modification from DCM (A). The syntheses of the target molecules were attempted from 4-hydroxy-6-methyl-2-pyrone, as starting material through either four or six step reactions. As a result, three kinds of compounds (1-3) were prepared. The optical properties of all the synthetic compounds were examined by UV and fluorescence spectrophotometry. Photoluminescent data of each red emitters showed emission λmax values of 637 nm (DCJTB), 607 nm (1), 508 nm (2) and 598 nm (3), respectively at very dilute concentration. The band gap energies of (DCJTB and 1-3) calculated from photoluminescent spectra were 2.12, 2.27, 2.35 and 2.46 eV, respectively. The relative quantum yields of the red emitters (DCJTB and 1-3) determined by fluorescence spectroscopic analysis were 11, 24, 0.3 and 10%, respectively. Throughout observation of all the optical data, DCJTB is the most efficient red emitter to display emission λmax value around 650 nm. The compound (1) has the highest relative quantum yield among the materials described in this research.
(-)-Ovalicin 유도체의 핵심 중간체에 대한 합성
남궁성건,이방숙,김은옥 서울여자대학교 자연과학연구소 2002 자연과학연구논문집 Vol.14 No.-
본 연구에서는 새로운 형태의 antl-angiogenic agent를 개발하기 위하여 anti-angiogenic activity를 나타내는 (-)-Ovalicin 의 구조를 변형한 target molecule (3)을 설계하고 이 화합물의 합성을 위한 핵심 중간체인 화합물 (5)를 합성하였다. 핵심 중간체 (5)는 출발 물질인 (-)-quinic acid로부터 합성하였는데 먼저 산 촉매 존재 하에 (-)-quinic acid 의 C-4, 5 위치에 acetal protection과 동시에 C-1, 3 위치에 lactone formation 및 lactone (6) 의 methanolysis를 통하여 화합물 (7)을 합성 한 다음 sec-alcohol group의 oxidation과 tert-alcohol group의 chlorination 및 C-1, 2 위치에 연속적인 elimination으로 conjugation된 ester (8)을 얻었다. 화합물 (8)의 bezylidene acetal deprotection 과 diol (9)에 silyl group protection 및 화합물 (10)에 NaBH₄를 사용한 선택적인 carbonyl group reduction을 통하여 화합물 (11)을 합성하였다. Alcohol (11)의 methylation과 ester (12) 의 DIBAH reductioin 및 화합물 (13) 의 al1ylic double bond 에 stereoselective epoxidation으로 핵심 중간체 (5)를 얻었으며 전체적으로는(-)-quinic acid로 부터 10단계의 합성 과정을 거쳐 6%의 총 수율로 핵심 중간체 (5)를 합성하였다. 핵심 중간체 (5) 로부터 화합물 (4)를 포함한 4-6 단계의 합성 과정을 통하여 target molecule (3) 을 얻을 수 있을 것으로 기대된다. To develope new type of anti-angiogenic agent, the target molecule (3) was designed through structural modification from (-)-Ovalicin. Its key intermediate (5) for the synthesis of the target molecule (3) was synthesized from (-)-quinic acid, as a starting material. Acetal protection at C-4, 5 position, followed by simultaneous lactone formation at C-1, 3 position of (-)-quinic acid in the presence of acid catalyst and methanolysis of the lactone (6) gave the compound (7). Oxidation of the sec- alcohol group, chlorination of the tert-alcohol group, sequential elimination at C-1, 2 position of the compound (7) produced the conjugated ester (8). Benzylidene acetal deprotection on the compound (8), introductioin of silyl protecting groups to the diol (9) and selective carbonyl group reduction of compound (10) with NaBH₄ gave the alcohol (11). Methylation of the alcohol (11), reduction of the ester (12) with DIBAH and stereoselective epoxidation at the allylic double bond of the compound (13) produced the key intermediate (5). In summary, the key intermediate (5) was synthesized from (-)-quinic acid through 10 reaction steps in 6% overall yield. The target molecule (3) is expected to be obtained from the key intermediate (5) via the compound (4) through 4-6 reaction steps.
남궁성건 서울여자대학교 자연과학연구소 1997 자연과학연구논문집 Vol.8 No.-
제초제들의 target 효소인 Acetolactate Synthase(ALS)의 저해제들로서 아미노퀴놀린 또는 아미노이소퀴놀린이 결합된 트리아졸로피리미딘 슬폰아미드(TP) 유도체들을 디자인 및 합성하였다. 이 퀴놀린 유도체 들은 신물질로서 2,6-difluoroanline그룹을 포함하는 기존의 상용 TP계 제초제인 Flumetsulam 및 그 유도체(0A)와 함께 보리 및 recombinant tobacco(대장균에서 발현)에서 분리, 정제한 ALS들에 대하여 억제력을 테스트하였다. 그 결과, 퀴놀린의 고리 질소를 중심으로 슬폰아미드기가 8-위치에 연결된 TP화합물은 기존의 제초제들 보다 더욱 탁월한 억제력을 나타내었으며 또한 퀴놀린 고리의 7-위치에 치환기가 존재하는 TP계 제초제들의 개발을 촉진시키는 선도 물질로서의 가능성도 보여주었다.