Structure Revision of Asperjinone Using Computer-Assisted Structure Elucidation Methods

被引：26

作者：

Elyashberg, Mikhail ^{[1
]}

Blinov, Kirill ^{[1
]}

Molodtsov, Sergey ^{[2
]}

Williams, Antony J. ^{[3
]}

机构：

[1] Moscow Dept, Moscow 117513, Russia

[2] Russian Acad Sci, Siberian Div, Novosibirsk Organ Chem Inst, Novosibirsk 630090, Russia

[3] Royal Soc Chem, Wake Forest, NC 27587 USA

来源：

JOURNAL OF NATURAL PRODUCTS | 2013年 / 76卷 / 01期

关键词：

D O I：

10.1021/np300218g

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The elucidated structure of asperjinone (1), a natural product isolated from thermophilic Aspergillus terreus, was revised using the expert system Structure Elucidator. The reliability of the revised structure (2) was confirmed using 180 structures containing the (3,3-dimethyloxiran-2-yl)methyl fragment (3) as a basis for comparison and whose chemical shifts contradict the suggested structure (1).

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页码：113 / 116

页数：4

相关论文

共 10 条

[1] Identification of Multiple Impurities in a Pharmaceutical Matrix Using Preparative Gas Chromatography and Computer-Assisted Structure Elucidation [J].

Codina, Anna ;

Ryan, Robert W. ;

Joyce, Richard ;

Richards, Don S. .

ANALYTICAL CHEMISTRY, 2010, 82 (21) :9127-9133

[2]

Elyashberg M, 2012, NEW DEV NMR, P1

[3] Computer-assisted structure verification and elucidation tools in NMR-based structure elucidation [J].

Elyashberg, M. E. ;

Williams, Aj. ;

Martin, G. E. .

PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 2008, 53 (1-2) :1-104

[4] Structure elucidator: A versatile expert system for molecular structure elucidation from 1D and 2D NMR data and molecular fragments [J].

Elyashberg, ME ;

Blinov, KA ;

Williams, AJ ;

Molodtsov, SG ;

Martin, GE ;

Martirosian, ER .

JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 2004, 44 (03) :771-792

[5] Elucidating 'undecipherable' chemical structures using computer-assisted structure elucidation approaches [J].

Elyashberg, Mikhail ;

Blinov, Kirill ;

Molodtsov, Sergey ;

Williams, Antony .

MAGNETIC RESONANCE IN CHEMISTRY, 2012, 50 (01) :22-27

[6] Structural revisions of natural products by Computer-Assisted Structure Elucidation (CASE) systems [J].

Elyashberg, Mikhail ;

Williams, Antony J. ;

Blinov, Kirill .

NATURAL PRODUCT REPORTS, 2010, 27 (09) :1296-1328

[7] Asperjinone, a Nor-Neolignan, and Terrein, a Suppressor of ABCG2-Expressing Breast Cancer Cells, from Thermophilic Aspergillus terreus [J].

Liao, Wen-Ying ;

Shen, Chia-Ning ;

Lin, Li-Hua ;

Yang, Yu-Liang ;

Han, Hsin-Ying ;

Chen, Jing-Wei ;

Kuo, Sheng-Chu ;

Wu, Shih-Hsiung ;

Liaw, Chih-Chuang .

JOURNAL OF NATURAL PRODUCTS, 2012, 75 (04) :630-635

[8] Toward more reliable 13C and 1H chemical shift prediction:: A systematic comparison of neural-network and least-squares regression based approaches [J].

Smurnyy, Yegor D. ;

Blinov, Kirill A. ;

Churanova, Tatiana S. ;

Elyashberg, Mikhail E. ;

Williams, Antony J. .

JOURNAL OF CHEMICAL INFORMATION AND MODELING, 2008, 48 (01) :128-134

[9] Recent developments in automated structure elucidation of natural products [J].

Steinbeck, C .

NATURAL PRODUCT REPORTS, 2004, 21 (04) :512-518

[10] Applying computer-assisted structure elucidation algorithms for the purpose of structure validation: Revisiting the NMR assignments of hexacyclinol [J].

Williams, A. J. ;

Elyashberg, M. E. ;

Blinov, K. A. ;

Lankin, D. C. ;

Martin, G. E. ;

Reynolds, W. F. ;

Porco, J. A., Jr. ;

Singleton, C. A. ;

Su, S. .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (04) :581-588