440 0

형광체를 포함한 Uridine 유도체의 합성

Title
형광체를 포함한 Uridine 유도체의 합성
Other Titles
The synthesis of Uridine Derivative containing a Fluorophore
Author
김은영
Alternative Author(s)
Kim, Eun-Young
Advisor(s)
강용한
Issue Date
2008-02
Publisher
한양대학교
Degree
Master
Abstract
인간 게놈프로젝트의 주요 목표는 30억 개의 염기가 배열된 순서를 밝히는 일이다. 30억 개의 염기가 구체적으로 어떤 기능을 수행하는지, 그리고 사람마다 염기 서열이 어떻게 다른지가 밝혀져야 비로소 완벽한 생명의 설계도가 마련된다고 할 수 있다. 이러한 이유로 최근 들어 nucleosides에서 새롭고 독특한 생물학적, 화학적 특성을 제공하고자 base unit의 modification이 주목받고 있다. 본 연구에서는 DNA 서열을 인식하는데 사용할 수 있는 형광체를 포함한 uridine 유도체, 5-{3-[(coumarin-7-yl)methyl amino] propyn-1-yl}uridine (17)을 합성하였다. 2’,3’,5’-Tri-O-acetyl uri- dine (10)은 acetic anhydride를 사용하여 uridine (9)을 acetylation 하여 얻었다. Uridine 염기 10의 5-위치에 대한 요오드화 반응으로 5-iodo-2’,3’,5’-tri-O-acetyluridine (11)이 합성되었다. NaOMe를 사용한 화합물 11의 acetyl기의 제거로 5-iodouridine (12)가 얻어졌다. 5-Iodouridine (12)와 N-(2-propynyl)-2,2,2-trifluoro- acetamide (14)의 Sonogashira 반응으로 5-(3-aminopropyn-1- yl) uridine (16)이 합성되었으며, 화합물 16은 7-bromomethyl- coumarin (8)과의 짝지음 반응(coupling reaction)으로 목표 화합물 인 5-{3-[(coumarin-7-yl)methylamino]propyn-1-yl}uridine (17) 로 변환되었다.
The main objective of human genome project is one which reveals the sequence that thirty hundred million bases are arranged. Thirty hundred million bases should have accomplished a what kind of function concretely, and how it comes to reveal that base sequence of each person is different and there is a possibility of saying that at last the draft of the life which is perfect is prepared. In recent years, there has been remarkable interest in nucleosides in which the base unit has been modified to provide new and unique biological and chemical properties. In this study, uridine derivative containing a fluorophore, 5- {3-[(coumarin-7-yl)methylamino]propyn-1-yl}uridine (17), could be used for the detection of DNA sequences have been prepared. 2’,3’,5’-Tri-O-acetyluridine (10) was obtained from the reaction of uridine (9) by acetylation with acetic anhydride. 5-Iodo- 2’,3’,5’-tri-O-acetyluridine (11) was prepared through the iodination at C-5 position of uridine base 10. Deprotecting of acetyl group of 11 with sodium methoxide provided 5-iodouridine (12). The Sonogashira reaction of 5-iodouridine (12) with N-(2- propynyl)-2,2,2-trifluoroacetamide (14) gave 5-(3-aminopropyn- 1-yl)uridine (16) which was converted into the desired product, 5- {3-[(coumarin-7-yl)methylamino]propyn-1-yl}uridine (17) by the coupling reaction with 7-bromomethylcoumarin (8).
URI
https://repository.hanyang.ac.kr/handle/20.500.11754/147676http://hanyang.dcollection.net/common/orgView/200000409306
Appears in Collections:
GRADUATE SCHOOL[S](대학원) > APPLIED CHEMISTRY(응용화학과) > Theses (Master)
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE