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Unequivocal identification of two-bond heteronuclear correlations in natural products at nanomole scale by i-HMBC

Author

Listed:
  • Yunyi Wang

    (Merck & Co. Inc)

  • Aili Fan

    (Peking University)

  • Ryan D. Cohen

    (Merck & Co. Inc)

  • Guilherme Dal Poggetto

    (Merck & Co. Inc)

  • Zheng Huang

    (Merck & Co. Inc)

  • Haifeng Yang

    (Merck & Co. Inc)

  • Gary E. Martin

    (Seton Hall University)

  • Edward C. Sherer

    (Merck & Co. Inc)

  • Mikhail Reibarkh

    (Merck & Co. Inc)

  • Xiao Wang

    (Merck & Co. Inc)

Abstract

HMBC is an essential NMR experiment for determining multiple bond heteronuclear correlations in small to medium-sized organic molecules, including natural products, yet its major limitation is the inability to differentiate two-bond from longer-range correlations. There have been several attempts to address this issue, but all reported approaches suffer various drawbacks, such as restricted utility and poor sensitivity. Here we present a sensitive and universal methodology to identify two-bond HMBC correlations using isotope shifts, referred to as i-HMBC (isotope shift detection HMBC). Experimental utility was demonstrated at the sub-milligram / nanomole scale with only a few hours of acquisition time required for structure elucidation of several complex proton-deficient natural products, which could not be fully elucidated by conventional 2D NMR experiments. Because i-HMBC overcomes the key limitation of HMBC without significant reduction in sensitivity or performance, i-HMBC can be used as a complement to HMBC when unambiguous identifications of two-bond correlations are needed.

Suggested Citation

  • Yunyi Wang & Aili Fan & Ryan D. Cohen & Guilherme Dal Poggetto & Zheng Huang & Haifeng Yang & Gary E. Martin & Edward C. Sherer & Mikhail Reibarkh & Xiao Wang, 2023. "Unequivocal identification of two-bond heteronuclear correlations in natural products at nanomole scale by i-HMBC," Nature Communications, Nature, vol. 14(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-37289-z
    DOI: 10.1038/s41467-023-37289-z
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    References listed on IDEAS

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    1. Maria Theresia Pöschko & Victor V. Rodin & Judith Schlagnitweit & Norbert Müller & Hervé Desvaux, 2017. "Nonlinear detection of secondary isotopic chemical shifts in NMR through spin noise," Nature Communications, Nature, vol. 8(1), pages 1-9, April.
    2. Maria Theresia Pöschko & Victor V. Rodin & Judith Schlagnitweit & Norbert Müller & Hervé Desvaux, 2017. "Erratum: Nonlinear detection of secondary isotopic chemical shifts in NMR through spin noise," Nature Communications, Nature, vol. 8(1), pages 1-1, April.
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