Efficient Protocol for Accurately Calculating <sup>13</sup>C Chemical Shifts of Conformationally Flexible Natural Products: Scope, Assessment, and Limitations

DOI Web Site 被引用文献39件
  • Warren Hehre
    Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, California 92612-1542, United States
  • Phillip Klunzinger
    Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, California 92612-1542, United States
  • Bernard Deppmeier
    Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, California 92612-1542, United States
  • Andy Driessen
    Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, California 92612-1542, United States
  • Noritaka Uchida
    Wavefunction Japan, 3-5-2, Koji-Machi, Chiyoda-Ku, Tokyo 102-0083, Japan
  • Masaru Hashimoto
    Faculty of Agriculture and Life Science, Hirosaki University, 3-Bunkyo-cho, Hirosaki 036-8561, Japan
  • Eri Fukushi
    Graduate School of Agriculture, Hokkaido University, Sapporo 060-8589, Japan
  • Yusuke Takata
    Graduate School of Agriculture, Hokkaido University, Sapporo 060-8589, Japan

書誌事項

公開日
2019-07-19
権利情報
  • https://doi.org/10.15223/policy-029
  • https://doi.org/10.15223/policy-037
  • https://doi.org/10.15223/policy-045
DOI
  • 10.1021/acs.jnatprod.9b00603
公開者
American Chemical Society (ACS)

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説明

An efficient protocol for calculating 13C NMR chemical shifts for natural products with multiple degrees of conformational freedom is described. This involves a multistep procedure starting from molecular mechanics and ending with a large basis set density functional model to obtain accurate Boltzmann conformer weights, followed by empirically corrected density functional NMR calculations for the individual conformers. The accuracy of the protocol (average rms <4 ppm) was determined by application to ∼925 diverse natural products, the structures of which have been confirmed either by X-ray crystallography or independent synthesis. The protocol was then applied to ∼ 2275 natural products, the structures of which were elucidated mainly by NMR and MS data. Five to ten percent of the latter compounds exhibited rms errors significantly in excess of 4 ppm, suggesting possible structural or signal assignment errors. Both data sets are available from an online browser ( NMR.wavefun.com ). The procedure can be and has been fully automated and is practical using present-generation personal computers, requiring a few hours or days depending on the size of the molecule and number of accessible conformers.

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