Structure verification through computer-assisted spectral assignment of NMR spectra

被引：15

作者：

Plainchont, Bertrand ^{[1
]}

Nuzillard, Jean-Marc ^{[1
]}

机构：

[1] Univ Reims, Inst Chim Mol Reims, CNRS, UMR 7312, F-51687 Reims 2, France

来源：

MAGNETIC RESONANCE IN CHEMISTRY | 2013年 / 51卷 / 01期

关键词：

NMR; H-1; C-13; HSQC; HMBC; COSY; automated structure verification; chemical shift prediction; structure revision; structure generation; STRUCTURE ELUCIDATION; AUTOMATIC-ANALYSIS; H-1-NMR; LOGIC;

D O I：

10.1002/mrc.3908

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The validation of a molecular organic structure on the basis of 1D and 2D HSQC, COSY and HMBC NMR spectra is proposed as an alternative to the methods that are mainly based on chemical shift prediction. The CCASA software was written for this purpose. It provides an updated and improved implementation of the preceding computer-assisted spectral assignment software. CCASA can be downloaded freely from http://www.univ-reims.fr/LSD/JmnSoft/CASA. Two bioactive natural products, a triterpene and a benzophenone, were selected from literature data as examples. The tentative matching between the structure and the NMR data interpretation of the triterpene unexpectedly leads to the hypothesis of an incorrect structure. The LSD software was used to find an alternative structure that improved the 2D NMR data interpretation and the carbon-13 chemical shift matching between experimental values and those produced by the nmrshiftdb2 prediction tool. The benzophenone example showed that signal assignment by means of chemical shift prediction can be replaced by elementary user-supplied chemical shift and multiplicity constraints. Copyright (C) 2012 John Wiley & Sons, Ltd.

引用

页码：54 / 59

页数：6

共 20 条

[1] Prediction of 1H NMR chemical shifts using neural networks [J].

Aires-de-Sousa, J ;

Hemmer, MC ;

Gasteiger, J .

ANALYTICAL CHEMISTRY, 2002, 74 (01) :80-90

[2] Bioactive benzophenones from Garcinia xanthochymus fruits [J].

Baggett, S ;

Protiva, P ;

Mazzola, EP ;

Yang, H ;

Ressler, ET ;

Basile, MJ ;

Weinstein, IB ;

Kennelly, EJ .

JOURNAL OF NATURAL PRODUCTS, 2005, 68 (03) :354-360

[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] Automated structure verification based on a combination of 1D 1H NMR and 2D 1H-13C HSQC spectra [J].

Golotvin, Sergey S. ;

Vodopianov, Eugene ;

Pol, Rostislav ;

Lefebvre, Brent A. ;

Williams, Antony J. ;

Rutkowske, Randy D. ;

Spitzer, Timothy D. .

MAGNETIC RESONANCE IN CHEMISTRY, 2007, 45 (10) :803-813

[5] Concurrent combined verification: reducing false positives in automated NMR structure verification through the evaluation of multiple challenge control structures [J].

Golotvin, Sergey S. ;

Pol, Rostislav ;

Sasaki, Ryan R. ;

Nikitina, Asya ;

Keyes, Philip .

MAGNETIC RESONANCE IN CHEMISTRY, 2012, 50 (06) :429-435

[6] Automated structure verification based on 1H NMR prediction [J].

Golotvin, SS ;

Vodopianov, E ;

Lefebvre, BA ;

Williams, AJ ;

Spitzer, TD .

MAGNETIC RESONANCE IN CHEMISTRY, 2006, 44 (05) :524-538

[7] Towards the automatic analysis of 1H NMR spectra:: Part 3.: Confirmation of postulated chemical structure [J].

Griffiths, L ;

Bright, JD .

MAGNETIC RESONANCE IN CHEMISTRY, 2002, 40 (10) :623-634

[8] Towards the automatic analysis of NMR spectra:: Part 7.: Assignment of 1H by employing both 1H and 1H/13C correlation spectra [J].

Griffiths, Lee ;

Beeley, Howard H. ;

Horton, Rob .

MAGNETIC RESONANCE IN CHEMISTRY, 2008, 46 (09) :818-827

[9] Automated compound verification using 2D-NMR HSQC data in an open-access environment [J].

Keyes, Philip ;

Hernandez, Gonzalo ;

Cianchetta, Giovanni ;

Robinson, James ;

Lefebvre, Brent .

MAGNETIC RESONANCE IN CHEMISTRY, 2009, 47 (01) :38-52

[10]

Nuzillard JM, 2003, CHINESE J CHEM, V21, P1263

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