Recent Advances in the Synthetic Studies of Nine-membered Enediyne Antitumor Antibiotics

被引:3
|
作者
Sato, Itaru [1 ]
Hirama, Masahiro
机构
[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan
基金
日本科学技术振兴机构;
关键词
KEDARCIDIN CHROMOPHORE; MADUROPEPTIN CHROMOPHORE; C-1027; CHROMOPHORE; NEOCARZINOSTATIN CHROMOPHORE; ENANTIOSELECTIVE SYNTHESIS; ARYL ETHER; ABSOLUTE STEREOCHEMISTRY; EFFICIENT CONSTRUCTION; STRUCTURE ELUCIDATION; CARBOXYLIC ESTERS;
D O I
10.5059/yukigoseikyokaishi.68.1123
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chromophores of the chromoprotein antibiotics C-1027, kedarcidin, and maduropeptin feature a unique nine-membered enediyne structure in the ansa-macrolide ring and show extremely potent cytotoxicity. Their complicated fused ring systems were recently synthesized and the total synthesis of (-)-maduropeptin chromophore was achieved, which thereby led to the revision of its stereochemical structure.
引用
收藏
页码:1123 / 1131
页数:9
相关论文
共 42 条
  • [1] Predictive Model for Epoxide Hydrolase-Generated Stereochemistry in the Biosynthesis of Nine-Membered Enediyne Antitumor Antibiotics
    Horsman, Geoffrey P.
    Lechner, Anna
    Ohnish, Yasuo
    Moore, Bradley S.
    Shen, Ben
    [J]. BIOCHEMISTRY, 2013, 52 (31) : 5217 - 5224
  • [2] Evidence for spontaneous cycloaromatization of nine-membered monocyclic enediyne
    Mita, T
    Kawata, S
    Hirama, M
    [J]. CHEMISTRY LETTERS, 1998, (09) : 959 - 960
  • [3] Recent Advances on the Synthesis of Nine-Membered N-Heterocycles
    Qin Xiaoting
    Zou Ning
    Nong Caimei
    Mo Dongliang
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (01) : 130 - 155
  • [4] Photochemical Generation and Reversible Cycloaromatization of a Nine-Membered Ring Cyclic Enediyne
    Pandithavidana, Dinesh R.
    Poloukhtine, Andrei
    Popik, Vladimir V.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (01) : 351 - 356
  • [5] RECENT STUDIES OF THE ENEDIYNE ANTIBIOTICS
    MYERS, AG
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 206 : 154 - ORGN
  • [6] Internal amide-triggered cycloaromatization of maduropeptin-like nine-membered enediyne
    Norizuki, Yutaro
    Komano, Kazuo
    Sato, Itaru
    Hirama, Masahiro
    [J]. CHEMICAL COMMUNICATIONS, 2008, (42) : 5372 - 5374
  • [7] A new approach to nine-membered enediyne using a palladium catalyzed cross-coupling reaction
    Tanaka, H
    Yamada, H
    Matsuda, A
    Takahashi, T
    [J]. SYNLETT, 1997, (04) : 381 - &
  • [8] Synthesis of nine-membered, masked enediyne analogues with DNA intercalators and its DNA cleaving activities
    Takahashi, T
    Tanaka, H
    Yamada, H
    Matsumoto, T
    Sugiura, Y
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (13-14): : 1524 - 1526
  • [9] Synthesis and chemistry of chromoprotein antitumor antibiotics: Nine-membered enediynes are equilibrated with p-benzyne type biradicals
    Hirama, M
    [J]. PURE AND APPLIED CHEMISTRY, 1997, 69 (03) : 525 - 530
  • [10] Draft Genome Sequence of Streptomyces globisporus C-1027, Which Produces an Antitumor Antibiotic Consisting of a Nine-Membered Enediyne with a Chromoprotein
    Wang, Lifei
    Wang, Songmei
    He, Qing
    Yu, Tengfei
    Li, Qinglian
    Hong, Bin
    [J]. JOURNAL OF BACTERIOLOGY, 2012, 194 (15) : 4144 - 4144