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Racing toward Fast and Effective 17O Isotopic Labeling and Nuclear Magnetic Resonance Spectroscopy of N-Formyl-MLF-OH and Associated Building Blocks

Cite this: J. Phys. Chem. B 2021, 125, 43, 11916–11926
Publication Date (Web):October 25, 2021
https://doi.org/10.1021/acs.jpcb.1c07397
Copyright © 2021 American Chemical Society

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    Abstract

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    Solid-state 1H, 13C, and 15N nuclear magnetic resonance (NMR) spectroscopy has been an essential analytical method in studying complex molecules and biomolecules for decades. While oxygen-17 (17O) NMR is an ideal and robust candidate to study hydrogen bonding within secondary and tertiary protein structures for example, it continues to elude many. We discuss an improved multiple-turnover labeling procedure to develop a fast and cost-effective method to 17O label fluoroenylmethyloxycarbonyl (Fmoc)-protected amino acid building blocks. This approach allows for inexpensive ($0.25 USD/mg) insertion of 17O labels, an important barrier to overcome for future biomolecular studies. The 17O NMR results of these building blocks and a site-specific strategy for labeled N-acetyl-MLF-OH and N-formyl-MLF-OH tripeptides are presented. We showcase growth in NMR development for maximizing sensitivity gains using emerging sensitivity enhancement techniques including population transfer, high-field dynamic nuclear polarization, and cross-polarization magic-angle spinning cryoprobes.

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.jpcb.1c07397.

    • Mass spectra of 17O-enriched Fmoc-Met-OH, Fmoc-Leu-OH, Fmoc-Phe-OH, and N-formyl-ML*F-OH, nonspinning 17O NMR spectra of Fmoc-Met-OH, Fmoc-Leu-OH, and Fmoc-Phe-OH, and 17O NMR spectra of recrystallized Fmoc-Met-OH (PDF)

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    Cited By

    This article is cited by 5 publications.

    1. Ivan Hung, Eric G. Keeler, Wenping Mao, Peter L. Gor’kov, Robert G. Griffin, Zhehong Gan. Residue-Specific High-Resolution 17O Solid-State Nuclear Magnetic Resonance of Peptides: Multidimensional Indirect 1H Detection and Magic-Angle Spinning. The Journal of Physical Chemistry Letters 2022, 13 (28) , 6549-6558. https://doi.org/10.1021/acs.jpclett.2c01777
    2. Ivan Hung, Wenping Mao, Eric G. Keeler, Robert G. Griffin, Peter L. Gor'kov, Zhehong Gan. Characterization of peptide O⋯HN hydrogen bonds via 1 H-detected 15 N/ 17 O solid-state NMR spectroscopy. Chemical Communications 2023, 59 (21) , 3111-3113. https://doi.org/10.1039/D2CC07004A
    3. Jessica Špačková, Ieva Goldberga, Rishit Yadav, Guillaume Cazals, Aurélien Lebrun, Pascal Verdié, Thomas‐Xavier Métro, Danielle Laurencin. Fast and Cost‐Efficient 17 O‐Isotopic Labeling of Carboxylic Groups in Biomolecules: From Free Amino Acids to Peptide Chains. Chemistry – A European Journal 2023, 29 (10) https://doi.org/10.1002/chem.202203014
    4. Riley W. Hooper, Diganta Sarkar, Vladimir K. Michaelis. Bulk and nanoscale semiconducting materials: Structural advances using solid-state NMR spectroscopy. Current Opinion in Colloid & Interface Science 2022, 62 , 101631. https://doi.org/10.1016/j.cocis.2022.101631
    5. Jiahui Shen, Victor Terskikh, Jochem Struppe, Alia Hassan, Martine Monette, Ivan Hung, Zhehong Gan, Andreas Brinkmann, Gang Wu. Solid-state 17 O NMR study of α- d -glucose: exploring new frontiers in isotopic labeling, sensitivity enhancement, and NMR crystallography. Chemical Science 2022, 13 (9) , 2591-2603. https://doi.org/10.1039/D1SC06060K

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