Synthesis and study on biological activity of quinoxalyl octadepsipeptide = 퀴녹살릴 옥타뎁시펩타이드의 합성 및 생체활성의 연구

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Echinomycin is well known to natural product which shows strong antibiotic activity. Its outer quinoxaline rings have a important role of bis-intercalating around the DNA, and the $C_2$-symmetric peptide also has an interesting biological activity. Connection with the synthesis of echinomycin analogue, new quinoxaline antibiotics which have a cyclic octadepsipeptide but different inner bridge $(-CH_2-S-CH_2-S-CH_2-)$ havw been synthesized. $C_2$-symmetric cyclic octadepsipeptide have been prepared from tradepsipeptide, Cbz-D-Ser[H-Ala-MeCys(Bam)-Me-Val]-OPa, as a key intermediate. New quinoxalyl compounds (66 and 69) were prepared from 55 through 3 steps. Their oxidized forms (67, 68, 70 and 71) were also prepared by oxidation with m-CPBA or dimethyldioxirane. Cytotoxcities of YK-2000 - 2003 against human cancer cell were measured. The YK-2000(66) shows a similar cytotoxicity to echinomycin.
Advisors
Kim, Yong-Hae김용해
Description
한국과학기술원 : 화학과,
Publisher
한국과학기술원
Issue Date
2002
Identifier
173592/325007 / 020003112
Language
eng
Description

학위논문(석사) - 한국과학기술원 : 화학과, 2002.2, [ iii, 45 p. ]

Keywords

DNA intercalator; anti-cancer activity; Echinomycin; Octadepsipeptide; 인터킬레이터; 옥타뎁시펩타이드; 항암특성; 이치노마이신

URI
http://hdl.handle.net/10203/31898
Link
http://library.kaist.ac.kr/search/detail/view.do?bibCtrlNo=173592&flag=dissertation
Appears in Collection
CH-Theses_Master(석사논문)
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