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Issue 43, 2013
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Effective synthesis of kynurenine-containing peptides via on-resin ozonolysis of tryptophan residues: synthesis of cyclomontanin B

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Abstract

The preparation of Kyn-containing peptides is difficult, owing to the low reactivity of Kyn in the coupling reaction. In this report, Kyn-containing peptides were efficiently obtained via on-resin ozonolysis of the corresponding Trp-containing peptide. In addition, a Kyn-containing cyclic peptide, cyclomontanin B, has been synthesized by this strategy in the combination with serine/threonine ligation (STL)-mediated cyclization.

Graphical abstract: Effective synthesis of kynurenine-containing peptides via on-resin ozonolysis of tryptophan residues: synthesis of cyclomontanin B

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Publication details

The article was received on 09 Aug 2013, accepted on 11 Sep 2013 and first published on 12 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41631C
Citation: Org. Biomol. Chem., 2013,11, 7616-7620
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    Effective synthesis of kynurenine-containing peptides via on-resin ozonolysis of tryptophan residues: synthesis of cyclomontanin B

    C. T. T. Wong, H. Y. Lam and X. Li, Org. Biomol. Chem., 2013, 11, 7616
    DOI: 10.1039/C3OB41631C

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