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

original image

Snipping tool: Zn(OTf)2 is an efficient catalyst for selective cleavage of amides bearing a β-hydroxyethyl group on the nitrogen atom. The mechanism involves an N,O-acyl rearrangement and transesterification. This new catalytic system can be applied to sequence-specific peptide bond scission at the amine side of a serine residue. Tf=trifluoromethanesulfonyl.

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