The structures of fluostatins C, D and E, novel members of the fluostatin family

被引:24
作者
Schneider, K
Nicholson, G
Ströbele, M
Baur, S
Niehaus, J
Fiedler, HP
Süssmuth, RD
机构
[1] Tech Univ Berlin, Inst Organ Chem, D-10623 Berlin, Germany
[2] Univ Tubingen, Inst Organ Chem, D-72076 Tubingen, Germany
[3] Univ Tubingen, Inst Anorgan Chem, D-72076 Tubingen, Germany
[4] Univ Tubingen, Inst Mikrobiol, D-72076 Tubingen, Germany
关键词
fluostatin; kinamycin; structure elucidation;
D O I
10.1038/ja.2006.15
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Three new fluostatin antibiotics have been isolated from the culture filtrate of Streptomyces strain Acta 1383. The chemical structures of these compounds were determined by mass spectrometry and NMR spectroscopy. The relative configuration has been determined by X-ray crystal structure analysis and the absolute configuration was deduced from NMR data with the help of Helmchen esters. These compounds represent the first reported epoxide fluostatins (1, 2) and underline previously found analogies to the group of kinamycin antibiotics.
引用
收藏
页码:105 / 109
页数:5
相关论文
共 9 条
[1]   Fluostatins A and B, new inhibitors of dipeptidyl peptidase III, produced by Streptomyces sp. TA-3391 -: II.: Structure determination [J].
Akiyama, T ;
Nakamura, KT ;
Takahashi, Y ;
Naganawa, H ;
Muraoka, Y ;
Aoyagi, T ;
Takeuchi, T .
JOURNAL OF ANTIBIOTICS, 1998, 51 (06) :586-588
[2]  
[Anonymous], 1993, NAT PROD LETT
[3]  
BAUR S, UNPUB J ANTIBIOT
[4]   AN EMPIRICAL CORRECTION FOR ABSORPTION ANISOTROPY [J].
BLESSING, RH .
ACTA CRYSTALLOGRAPHICA SECTION A, 1995, 51 :33-38
[5]   Biosynthesis of the kinamycins [J].
Gould, SJ .
CHEMICAL REVIEWS, 1997, 97 (07) :2499-2509
[6]  
HELMCHEN G, 1974, TETRAHEDRON LETT, P1527
[7]   Isoprekinamycin is a diazobenzo[a]fluorene rather than a diazobenzo[b]fluorene [J].
Proteau, PJ ;
Li, YF ;
Chen, J ;
Williamson, RT ;
Gould, SJ ;
Laufer, RS ;
Dmitrienko, GI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8325-8326
[8]  
SHELDRICK GM, 1997, SHELX97 U GOTTINGEN
[9]   FL-120A-SIMILAR-TO-D', NEW PRODUCTS RELATED TO KINAMYCIN FROM STREPTOMYCES-CHATTANOOGENSIS SUBSP TAITUNGENSIS SUBSP NOV .2. ISOLATION AND STRUCTURE DETERMINATION [J].
YOUNG, JJ ;
HO, SN ;
JU, WM ;
CHANG, LR .
JOURNAL OF ANTIBIOTICS, 1994, 47 (06) :681-687