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

Yunyi Wang, Aili Fan, Ryan D. Cohen, Guilherme Dal Poggetto, Zheng Huang, Haifeng Yang, Gary E. Martin, Edward C. Sherer, Mikhail Reibarkh () and Xiao Wang ()
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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

Nature Communications, 2023, vol. 14, issue 1, 1-11

Abstract: 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.

Date: 2023
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DOI: 10.1038/s41467-023-37289-z

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