DC Field | Value | Language |
---|---|---|
dc.contributor.advisor | 한순규 | - |
dc.contributor.author | Jang, Youngho | - |
dc.contributor.author | 장영호 | - |
dc.date.accessioned | 2024-07-26T19:31:04Z | - |
dc.date.available | 2024-07-26T19:31:04Z | - |
dc.date.issued | 2023 | - |
dc.identifier.uri | http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=1047428&flag=dissertation | en_US |
dc.identifier.uri | http://hdl.handle.net/10203/321001 | - |
dc.description | 학위논문(박사) - 한국과학기술원 : 화학과, 2023.8,[iv, 169 p. :] | - |
dc.description.abstract | This thesis is divided into two chapters. Each chapter describes the total synthesis of dimeric Drimane Sesquiterpenes and the effectiveness of the newly developed antiviral agents over various SARS-CoV-2 variants hints at the broad-spectrum antiviral efficacy of saponin-based therapeutics against future coronavirus variants. Chapter 1 describe the first total synthesis of cinnamodial-based dimer (–)-capsicodendrin. Firstly, we developed a 12-step synthetic route to access (–)-cinnamodial from 1-vinyl-2,6,6-trimethylcyclohexene. We then showed that (–)-cinnamodial can selectively dimerize to (–)-capsicodendrin under kinetically controlled basic conditions. Our observations regarding a facile conversion of (–)-capsicodendrin back to (–)-cinnamodial hint at the possibility that (–)-capsicodendrin is a chemical reservoir of insecticidal (–)-cinnamodial and Cinnamosma genus plants release it upon environmental stresses. Chapter 2 discovered that the C3-glucose, the C28-oligosaccharide moiety that consist of (→3)-β-D-Xyl-(1→4)- α-L-Rham-(1→2)-β-D-Ara-(1→) as the last three sugar units, and the C16-hydroxyl group were critical components of saponin-based coronavirus cell entry inhibitors. These findings enabled us to develop minimal saponin-based antiviral agents that are 1.6 to 2 times more potent than the originally discovered platycodin D. We found that our saponin-based antiviral agents inhibited both the endosomal and transmembrane protease serine 2-mediated cell surface viral entries. Cell fusion assay experiment revealed that our newly developed compounds inhibit the SARS-CoV-2 entry by blocking the fusion between the viral and host cell membranes. The effectiveness of the newly developed antiviral agents over various SARS-CoV-2 variants hints at the broadspectrum antiviral efficacy of saponin-based therapeutics against future coronavirus variants. | - |
dc.language | eng | - |
dc.publisher | 한국과학기술원 | - |
dc.subject | 드리메인 세스퀴테르펜▼a천연물 합성▼a코로나바이러스▼a분자간 자가조립▼a사포닌 유도체 | - |
dc.subject | Drimane sesquiterpenes▼aTotal synthesis▼aCOVID-19▼aSARS-CoV-2▼aSaponins | - |
dc.title | Bioinspired total synthesis of Capsicodendrin and synthesis of Saponin derivatives for prevention and treatment of enveloped virus-mediated infectious diseases | - |
dc.title.alternative | 생합성 가설을 기반으로 한 캅시코덴드린 전합성 연구와 외막형 바이러스 기반 감염병의 예방 및 치료용 사포닌 유도체 합성에 관한 연구 | - |
dc.type | Thesis(Ph.D) | - |
dc.identifier.CNRN | 325007 | - |
dc.description.department | 한국과학기술원 :화학과, | - |
dc.contributor.alternativeauthor | Han, Sun Kyu | - |
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