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Zinc-Catalyzed Amide Cleavage and Esterification of β-Hydroxyethylamides

Authors

  • Dr. Yusuke Kita,

    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • Yuji Nishii,

    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • Takafumi Higuchi,

    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • Prof. Dr. Kazushi Mashima

    Corresponding author
    1. Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
    • Department of Chemistry, Graduate School of Engineering Science, Osaka University, CREST, Toyonaka, Osaka 560-8531 (Japan)
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  • This work is finantially supported by The Core Research for Evolutional Science and Technology (CREST), program of the Japan Science and Technology Agency (JST).

Abstract

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Schneidewerkzeug: Zn(OTf)2 ist ein effizienter Katalysator für die selektive Spaltung von Amiden mit β-Hydroxyethylgruppe am Stickstoffatom. Der Mechanismus umfasst eine N,O-Acylumlagerung und eine Umesterung. Das neue Katalysatorsystem kann auf die sequenzspezifische Spaltung von Peptidbindungen am Aminzentrum eines Serins angewendet werden. Tf=Trifluormethansulfonyl.

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