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Synthesis of bis-peptides attached on poly[n]norbornene molecular scaffolds with well-defined relative positions and distances

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Abstract

This article describes novel synthetic approaches to polynorbornene molecular scaffolds substituted with peptides at various, well-defined positions. A library of norbornene building blocks with attached peptides was prepared. Alkene cyclobutane epoxide (ACE) coupling method was used as a key step reaction for the connection of two norbornene building blocks into bis-peptide scaffolds. Photodimerization of cyclobutene diesters offers an alternative route to polynorbornene bis-peptides. Pyrrolo-peptides were used for preparation of peptide-substituted 7-aza norbornenes. Asymmetrical bis-peptide scaffolds were prepared by ACE coupling of peptide-norbornane epoxide with another norbornene-peptide block. Chemical elaboration of bridgehead dimethyl esters of ACE products or epoxide ACE reagents was also used for peptide attachment.

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Authors and Affiliations

  1. Centre for Molecular Architecture, Central Queensland University, Rockhampton, QLD, 4702, Australia

    Muhong Shang, Ronald N. Warrener & Douglas N. Butler

  2. Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan

    Yasujiro Murata

  3. Laboratory for Physical Organic Chemistry, Department of Organic Chemistry and Biochemistry, Ruder Bošković Institute, Bijenička c. 54, 10000, Zagreb, Croatia

    Davor Margetić

Authors
  1. Muhong Shang
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  2. Ronald N. Warrener
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  3. Douglas N. Butler
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  4. Yasujiro Murata
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  5. Davor Margetić
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Correspondence to Davor Margetić.

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Shang, M., Warrener, R.N., Butler, D.N. et al. Synthesis of bis-peptides attached on poly[n]norbornene molecular scaffolds with well-defined relative positions and distances. Mol Divers 15, 541–560 (2011). https://doi.org/10.1007/s11030-010-9279-9

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