1 Information and Communication Materials Lab. HanyangUniversity HanyangUniversity Resins 일반적으로 polystyrene (1-2 % divinylbenzene 으로 crosslink 된 ) 이.

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Information and Communication Materials Lab. HanyangUniversity HanyangUniversity Resins 일반적으로 polystyrene (1-2 % divinylbenzene 으로 crosslink 된 ) 이 많이 쓰임. 넓은 범위의 solvent polarity 에서 사용이 적합 resin 의 mechanical damage 가 적음 resin 의 interior area 가 넓음 Anchor groups for linking the substrate to the solid support Merrifield resin (cleavage : HF) Wang resin (cleavage : TFA) Rink resin (cleavage : 10% TFA) Trityl Chloride resin (cleavage : AcOH) Photolabile resin (cleavage : hv) Si containing resin (cleavage : TBAF) Polymeric Reagent  화학 반응이 진행하는 동안 reagent 로 작용하는 functional group 을 포함하고 있는 polymer. 2

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity Usages of Polymeric Reagents : Solid-Phase Organic Synthesis(SPOS)  Amide Bond Formation (natural biooligomer such as oligosaccharide, oligopetide unnatural biooligomer such as oligocarbamate, small molecule such as benzodiazepine)  Aromatic Substitutions(Heck, Friedel-Craft)  Condensations(Claisen, Aldol, )  Cycloaddition(Diels-Alder, )  Olefination(Wittig Reaction)  Grignard reagents  Michael additions  Nucleophilic substitutions 3

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity 4

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity 5

Resin 을 유기용매에 swelling 후 첫번째 amino acid 와 반응. Filter 를 하면 미반응 amino acid 와 용매는 여과됨. 다시 swelling 후 deprotect. 두번째 amino acid 와 반응 위와 같은 과정을 반복. Resin 에 연결된 oligopeptide 를 HF 를 사용 하여 떼어냄.

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity 2. Unnatural Biooligomer Peptide 구조가 체내에 있는 여러가지 효소에 의해 분해가 잘 일어남. 그러므로 peptidomestics( carbamate, urea, 등 ) 을 사 용하여 peptide 의 단점을 보완. 효소에 의해 잘 분해되지 않으며 효소나 수용체를 억제할 수 있는 새로운 약품으로써의 가능성을 지님. (1) Oligocarbamate Charles. Y. Cho, Peter G. Schultz, et. al., Science, Vol. 261, 1303(1993) Synthesis of oligocarbamate monomer 8

(2) Oligourea K. Burgess, D. S. Linthicum, and H. Shin, Angew. Chem. Int. Ed. Engl., 34, 907(1995) J. M. Kim et. al., Tetrahedron Lett., 37, 5305(1996) Synthesis of oligourea Monomer 9

3. Small Molecule (1) Benzodiazepine B. A. Bunin and J. A. Ellman, J. Am. Chem. Soc., 114, 10997(1992) Molecular weight 이 1000 이하인 화합물을 Small molecule 이라 함. 실제로 약효를 내는 화합물. Solid phase synthesis 의 장점을 이용하여 최 근에 제약회사를 중심으로 급격히 확산. Fmoc 으로 보호된 aminobenzophenone 유도 체를 Piperidine 으로 deprotect. Fmoc 으로 보호된 amino acid fluoride 와 반응. Piperidine 을 사용 deprotect 후.5% acetic acid 를 사용 60 o C 로 반응. Alkylation 을 통해 R 4 를 도입 후 TFA 로 resin 에서 분리. 10

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity 4.Oligosaccharide J.Y.Roberge et. al., Science, 269, 202 (1995) Hydroxy 기가 보호된 galactose glycal 을 단량체 로 사용. Legin 에 연결후 이중결합을 epoxydation 으로 활성화. 두번째 단량체 합성. 결합 – epoxidation 을 반복. Glucose 로 마무리. Cleave and deprotect. 11

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity - disadvantage main product 와 by-product(triphenylphosphine oxide) 간의 분리가 어려움. 시약의 가격이 많이 듬 - alkene products by polymerica phosphine reagents high purity, 정량적인 수율을 얻을 수 있음. 5. Wittig reaction 12

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity M. OGREN, K. HORNFELDT, K. J. FASTH AND B. LANGSTROM, Appl. Radiat. Iso., Vol. 46, No. 8, (1995)  Fast and efficient methods for the synthesis of 11 C- labelled terminal and branched alkenes 13

Information and Communication Materials Lab. HanyangUniversity HanyangUniversity