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J Am Chem Soc. 2011 May 25;133(20):7692-5. doi: 10.1021/ja2022027. Epub 2011 Apr 29.

The multiple multicomponent approach to natural product mimics: tubugis, N-substituted anticancer peptides with picomolar activity.

Author information

1
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle (Saale), Germany.

Abstract

The synthesis of a new generation of highly cytotoxic tubulysin analogues (i.e., tubugis) is described. In the key step, the rare, unstable, and synthetically difficult to introduce tertiary amide-N,O-acetal moiety required for high potency in natural tubulysins is replaced by a dipeptoid element formed in an Ugi four-component reaction. Two of the four components required are themselves produced by other multicomponent reactions (MCRs). Thus, the tubugis represent the first examples of the synthesis of natural-product-inspired compounds using three intertwined isonitrile MCRs.

PMID:
21528905
DOI:
10.1021/ja2022027
[Indexed for MEDLINE]

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