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Taguchi J, Ikeda T, Takahashi R, et al. Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate. Angew Chem Int Ed Engl. 2017;56(44):13847-13851doi: 10.1002/anie.201707933.
Taguchi, J., Ikeda, T., Takahashi, R., Sasaki, I., Ogasawara, Y., Dairi, T., Kato, N., Yamamoto, Y., Bode, J. W., & Ito, H. (2017). Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate. Angewandte Chemie (International ed. in English), 56(44), 13847-13851. https://doi.org/10.1002/anie.201707933
Taguchi, Jumpei, et al. "Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate." Angewandte Chemie (International ed. in English) vol. 56,44 (2017): 13847-13851. doi: https://doi.org/10.1002/anie.201707933
Taguchi J, Ikeda T, Takahashi R, Sasaki I, Ogasawara Y, Dairi T, Kato N, Yamamoto Y, Bode JW, Ito H. Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate. Angew Chem Int Ed Engl. 2017 Oct 23;56(44):13847-13851. doi: 10.1002/anie.201707933. Epub 2017 Sep 29. PMID: 28905460.
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Angew Chem Int Ed Engl. 2017 Oct 23;56(44):13847-13851. doi: 10.1002/anie.201707933. Epub 2017 Sep 29.

Synthesis of Acylborons by Ozonolysis of Alkenylboronates: Preparation of an Enantioenriched Amino Acid Acylboronate.

Angewandte Chemie (International ed. in English)

Jumpei Taguchi, Toshiki Ikeda, Rina Takahashi, Ikuo Sasaki, Yasushi Ogasawara, Tohru Dairi, Naoya Kato, Yasunori Yamamoto, Jeffrey W Bode, Hajime Ito

Affiliations

  1. Division of Applied Chemistry and Frontier Chemistry Center, Faculty of Engineering, Hokkaido University, Kita 13 Nishi 8 Kita-ku, Sapporo, Hokkaido, 060-8628, Japan.
  2. Department of Chemistry and Biological Science, College of Science and Engineering, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara-shi, 252-5258, Japan.
  3. Laboratorium für Organische Chemie, Department of Chemistry and Applied Bioscience, ETH Zürich, 8093, Zürich, Switzerland.

PMID: 28905460 DOI: 10.1002/anie.201707933

Abstract

A concise synthesis of acylborons was achieved by ozonolysis of alkenyl MIDA (N-methyliminodiacetic acid) boronates. This reaction exhibits excellent functional-group tolerance and is applicable to various acyl MIDA boronates and potassium acyltrifluroborates (KATs) which could not be synthesized by previous methods. In addition, α-amino acylborons, which would be essential for peptide ligations, were prepared for the first time. The acylboron of l-alanine was obtained in high enantiopurity and found to be configurationally stable. Oligopeptide synthesis between the α-amino KATs and amino acid in dilute aqueous media was studied.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: amino acids; boron; chemical ligation; ozonolysis; peptides

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