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

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 fo... Full description

Journal Title: Journal of the American Chemical Society 25 May 2011, Vol.133(20), pp.7692-5
Main Author: Pando, Orlando
Other Authors: Stark, Sebastian , Denkert, Annika , Porzel, Andrea , Preusentanz, Rainer , Wessjohann, Ludger A
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1520-5126 ; PMID: 21528905 Version:1 ; DOI: 10.1021/ja2022027
Link: http://pubmed.gov/21528905
Zum Text:
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recordid: medline21528905
title: The multiple multicomponent approach to natural product mimics: tubugis, N-substituted anticancer peptides with picomolar activity
format: Article
creator:
  • Pando, Orlando
  • Stark, Sebastian
  • Denkert, Annika
  • Porzel, Andrea
  • Preusentanz, Rainer
  • Wessjohann, Ludger A
subjects:
  • Molecular Mimicry
  • Antineoplastic Agents -- Pharmacology
  • Biological Products -- Chemistry
  • Peptides -- Pharmacology
ispartof: Journal of the American Chemical Society, 25 May 2011, Vol.133(20), pp.7692-5
description: 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.
language: eng
source:
identifier: E-ISSN: 1520-5126 ; PMID: 21528905 Version:1 ; DOI: 10.1021/ja2022027
fulltext: no_fulltext
issn:
  • 15205126
  • 1520-5126
url: Link


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titleThe multiple multicomponent approach to natural product mimics: tubugis, N-substituted anticancer peptides with picomolar activity
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subjectMolecular Mimicry ; Antineoplastic Agents -- Pharmacology ; Biological Products -- Chemistry ; Peptides -- Pharmacology
descriptionThe 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.
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descriptionThe 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.
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abstractThe 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.
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