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RESEARCH ARTICLE
Contents Vol 65(6)

The Synthesis of a Cubane-Substituted Dipeptide

Quentin I. Churches A , Roger J. Mulder A , Jonathan M. White B , John Tsanaktsidis A and Peter J. Duggan A C
+ Author Affiliations
- Author Affiliations

A CSIRO Materials Science and Engineering, Private Bag 10, Clayton South, Vic. 3169, Australia.

B School of Chemistry and Bio21 Molecular Science and Biotechnology Institute, University of Melbourne, Parkville, Vic. 3010, Australia.

C Corresponding author. Email: peter.duggan@csiro.au

Australian Journal of Chemistry 65(6) 690-693 https://doi.org/10.1071/CH12179
Submitted: 2 April 2012  Accepted: 2 May 2012   Published: 24 May 2012

Abstract

Amino acids and peptides bearing cyclic hydrocarbon side-chains are of interest in the development of a wide range of bioactive molecules. The preparation of an amino acid and a dipeptide derivative bearing an unfunctionalised cubane substituent is described. Attempts to prepare a cubylalanine derivative via the corresponding dehydroalanine were unsuccessful due to the high sensitivity of this vinyl cubane compound. Conversely, the addition of cubyllithium to a (RS)-glyoxylate sulfinimine led to an effective synthesis of a cubylglycine derivative and a cubane-substituted dipeptide in diastereomerically pure form.


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