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Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and 15N2-Diazirines and Their Application as Hyperpolarized Markers.

Publication ,  Journal Article
Glachet, T; Marzag, H; Saraiva Rosa, N; Colell, JFP; Zhang, G; Warren, WS; Franck, X; Theis, T; Reboul, V
Published in: Journal of the American Chemical Society
August 2019

A one-pot metal-free conversion of unprotected amino acids to terminal diazirines has been developed using phenyliodonium diacetate (PIDA) and ammonia. This PIDA-mediated transformation occurs via three consecutive reactions and involves an iodonitrene intermediate. This method is tolerant to most functional groups found on the lateral chain of amino acids, it is operationally simple, and it can be scaled up to provide multigram quantities of diazirine. Interestingly, we also demonstrated that this transformation could be applied to dipeptides without racemization. Furthermore, 14N2 and 15N2 isotopomers can be obtained, emphasizing a key trans-imination step when using 15NH3. In addition, we report the first experimental observation of 14N/15N isotopomers directly creating an asymmetric carbon. Finally, the 15N2-diazirine from l-tyrosine was hyperpolarized by a parahydrogen-based method (SABRE-SHEATH), demonstrating the products' utility as hyperpolarized molecular tag.

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Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

August 2019

Volume

141

Issue

34

Start / End Page

13689 / 13696

Related Subject Headings

  • Tyrosine
  • Onium Compounds
  • Nitrogen
  • Iodine
  • Imines
  • Halogenation
  • General Chemistry
  • Diazomethane
  • Ammonia
  • Amino Acids
 

Citation

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Glachet, T., Marzag, H., Saraiva Rosa, N., Colell, J. F. P., Zhang, G., Warren, W. S., … Reboul, V. (2019). Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and 15N2-Diazirines and Their Application as Hyperpolarized Markers. Journal of the American Chemical Society, 141(34), 13689–13696. https://doi.org/10.1021/jacs.9b07035
Glachet, Thomas, Hamid Marzag, Nathalie Saraiva Rosa, Johannes F. P. Colell, Guannan Zhang, Warren S. Warren, Xavier Franck, Thomas Theis, and Vincent Reboul. “Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and 15N2-Diazirines and Their Application as Hyperpolarized Markers.Journal of the American Chemical Society 141, no. 34 (August 2019): 13689–96. https://doi.org/10.1021/jacs.9b07035.
Glachet T, Marzag H, Saraiva Rosa N, Colell JFP, Zhang G, Warren WS, et al. Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and 15N2-Diazirines and Their Application as Hyperpolarized Markers. Journal of the American Chemical Society. 2019 Aug;141(34):13689–96.
Glachet, Thomas, et al. “Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and 15N2-Diazirines and Their Application as Hyperpolarized Markers.Journal of the American Chemical Society, vol. 141, no. 34, Aug. 2019, pp. 13689–96. Epmc, doi:10.1021/jacs.9b07035.
Glachet T, Marzag H, Saraiva Rosa N, Colell JFP, Zhang G, Warren WS, Franck X, Theis T, Reboul V. Iodonitrene in Action: Direct Transformation of Amino Acids into Terminal Diazirines and 15N2-Diazirines and Their Application as Hyperpolarized Markers. Journal of the American Chemical Society. 2019 Aug;141(34):13689–13696.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

August 2019

Volume

141

Issue

34

Start / End Page

13689 / 13696

Related Subject Headings

  • Tyrosine
  • Onium Compounds
  • Nitrogen
  • Iodine
  • Imines
  • Halogenation
  • General Chemistry
  • Diazomethane
  • Ammonia
  • Amino Acids