Stereostructure of a novel cytotoxic 18-membered macrolactone antibiotic FD-891

被引：22

作者：

Eguchi, T ^{[1
]}

Kobayashi, K

Uekusa, H

Ohashi, Y

Mizoue, K

Matsushima, Y

Kakinuma, K

机构：

[1] Tokyo Inst Technol, Dept Chem & Mat Sci, Meguro Ku, Tokyo 1528551, Japan

[2] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 20期

关键词：

D O I：

10.1021/ol026518k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations.

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页码：3383 / 3386

页数：4

相关论文

共 30 条

[1] Absolute stereochemistry of vicenistatin, a novel 20-membered macrocyclic lactam antitumor antibiotic [J].

Arai, H ;

Matsushima, Y ;

Eguchi, T ;

Shindo, K ;

Kakinuma, K .

TETRAHEDRON LETTERS, 1998, 39 (20) :3181-3184

[2] AN INTERNAL COORDINATE MONTE-CARLO METHOD FOR SEARCHING CONFORMATIONAL SPACE [J].

CHANG, G ;

GUIDA, WC ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4379-4386

[3]

*DEP CHEM, MACR VERS 6 5

[4] INHIBITORY EFFECT OF MODIFIED BAFILOMYCINS AND CONCANAMYCINS ON P-TYPE AND V-TYPE ADENOSINE-TRIPHOSPHATASES [J].

DROSE, S ;

BINDSEIL, KU ;

BOWMAN, EJ ;

SIEBERS, A ;

ZEECK, A ;

ALTENDORF, K .

BIOCHEMISTRY, 1993, 32 (15) :3902-3906

[5] Semisynthetic derivatives of concanamycin A and C, as inhibitors of V- and P-type ATPases:: Structure-activity investigations and developments of photoaffinity probes [J].

Dröse, S ;

Boddien, C ;

Gassel, M ;

Ingenhorst, G ;

Zeeck, A ;

Altendorf, K .

BIOCHEMISTRY, 2001, 40 (09) :2816-2825

[6] AN UNBOUNDED SYSTEMATIC SEARCH OF CONFORMATIONAL SPACE [J].

GOODMAN, JM ;

STILL, WC .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1991, 12 (09) :1110-1117

[7] PROBING THE CONFORMATIONAL SPACE AVAILABLE TO INHIBITORS IN THE THERMOLYSIN ACTIVE-SITE USING MONTE-CARLO ENERGY MINIMIZATION TECHNIQUES [J].

GUIDA, WC ;

BOHACEK, RS ;

ERION, MD .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1992, 13 (02) :214-228

[8] THE RELATIONSHIP BETWEEN PROTON-PROTON NMR COUPLING-CONSTANTS AND SUBSTITUENT ELECTRONEGATIVITIES .1. AN EMPIRICAL GENERALIZATION OF THE KARPLUS EQUATION [J].

HAASNOOT, CAG ;

DELEEUW, FAAM ;

ALTONA, C .

TETRAHEDRON, 1980, 36 (19) :2783-2792

[9]

Halgren TA, 1996, J COMPUT CHEM, V17, P520, DOI 10.1002/(SICI)1096-987X(199604)17:5/6<520::AID-JCC2>3.0.CO

[10]

2-W