Isolation and structure determination of a new inosine derivative of a marine natural product해양천연물인 새로운 이노신 유도체의 분리 및 구조결정

During the study on the biologically active compounds from Ligia Exotica, a new O$^\prime$-glycosyl inosine has been isolated as a new inosine nucleic acid derivative. It has been postulated that the new natural product is 3$^\prime$-O-glucosyl inosine derivative by $^1H$ NMR, $^{13}C$ NMR,FAB-MS, and UV spectra. In order to elucidate the structure, total synthesis has been examined. As a starting material, $^1N$-benzyl 5$^\prime$-O-acetyl inosine was used. It reacted with O-(2,3,4,6-tetra-O-benzyl-$\alpha$-glucosyl) trichloroacetimidate in the presence of $BF_3$ . $ET_2O$ in $CH_2Cl_2$ to give four different glucoside isomers, which were separated by preparative tlc (silica gel,solvent; $CH_2Cl_2$ : MeOH=30:1) after their deacetylation. Their debenzylation gave four different O$^\prime$-glucosyl inosine isomers. $^1H$-and $^{13}C$-nmr spectra of one of the four glucosides are identical with these from the natural product. I was concluded that new marine natural product is 3``-O-$\alpha$-glucosyl inosine by comparing the $^1H$,$^{13}C$ NMR chemical shifts of each four isomer with those of various spectral data which are already known.
Advisors
Kim, Yong-Hae(김용해)researcher
Publisher
한국과학기술원
Issue Date
1993
Identifier
68351/325007 / 000911089
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 1993.2, [ v, 43 p. ]

URI
http://hdl.handle.net/10203/32621
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=68351&flag=t
Appears in Collection
CH-Theses_Master(석사논문)
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