Research Article

Enhanced automated structure elucidation by inclusion of two-bond specific data

  1. Steve F. Cheatham1,*,
  2. Mike Kline1,
  3. Ryan R. Sasaki2,
  4. Kirill A. Blinov3,
  5. Mikhail E. Elyashberg3,
  6. Sergey G. Molodtsov4

Article first published online: 1 JUN 2010

DOI: 10.1002/mrc.2622

Issue

Magnetic Resonance in Chemistry

Magnetic Resonance in Chemistry

Volume 48, Issue 8, pages 571–574, August 2010

Additional Information

How to Cite

Cheatham, S. F., Kline, M., Sasaki, R. R., Blinov, K. A., Elyashberg, M. E. and Molodtsov, S. G. (2010), Enhanced automated structure elucidation by inclusion of two-bond specific data. Magnetic Resonance in Chemistry, 48: 571–574. doi: 10.1002/mrc.2622

Author Information

  1. 1

    DuPont Crop Protection, Stine-Haskell Research Center, Newark, DE 19714, USA

  2. 2

    Advanced Chemistry Development, Inc., Toronto, ON M5C 1T4, Canada

  3. 3

    Advanced Chemistry Development, Moscow Department, 6 Akademik Bakulev St., Moscow 117513, Russian Federation

  4. 4

    Siberian Branch of Russian Academy of Science, 9 Akademik Lavrent'ev Ave., Novosibirsk 630090, Russian Federation

*DuPont Crop Protection, Stine-Haskell Research Center, Newark, DE 19714 USA.

Publication History

  1. Issue published online: 9 JUL 2010
  2. Article first published online: 1 JUN 2010
  3. Manuscript Accepted: 28 APR 2010
  4. Manuscript Revised: 21 APR 2010
  5. Manuscript Received: 25 MAR 2010

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Keywords:

  • CASE;
  • 1,1-ADEQUATE;
  • H2BC;
  • structure elucidation;
  • retrorsine;
  • delcosine

Graphical Abstract

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A common problem in computer-assisted structure elucidation is the ambiguity in determining whether a cross peak in HMBC data is the result of 2, 3 or 4-bond correlations. The addition of the 2-bond specific experiment 1,1-ADEQUATE when used in combination with HSQC and HMBC data results in both increased accuracy and in a dramatic decrease in the time necessary for structure calculation. Optimization of sample conditions for use with a cryogenic probe permits routine acquisition of 1,1-ADEQUATE on a few milligrams of sample.

Abstract

The availability of cryogenically cooled probes permits routine acquisition of data from low sensitivity pulse sequences such as inadequate and 1,1-adequate. We demonstrate that the use of cryo-probe generated 1,1-adequate data in conjunction with HMBC dramatically improves computer-assisted structure elucidation (CASE) both in terms of speed and accuracy of structure generation. In this study data were obtained on two dissimilar natural products and subjected to CASE analysis with and without the incorporation of two-bond specific data. Dramatic improvements in both structure calculation times and structure candidates were observed by the inclusion of the two-bond specific data. Copyright © 2010 John Wiley & Sons, Ltd.

View Full Article with Supporting Information (HTML) Get PDF (130K)