Issue 36, 2013
From the journal:

Organic & Biomolecular Chemistry

Synthesis of homogeneous MUC1 oligomers via a bi-directional ligation strategy†

Dima Al Sheikha,a   Brendan L. Wilkinson,a   Gajan Santhakumar,a   Morten Thaysen-Andersenb  and  Richard J. Payne*a  

* Corresponding authors

a School of Chemistry, The University of Sydney, Sydney, NSW 2006, Australia
E-mail: richard.payne@sydney.edu.au
Fax: +64 2 9351 3329
Tel: +64 2 9351 5877

b Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia

Abstract

The efficient synthesis of homogeneous MUC1 peptide oligomers using sequential ligation reactions in the N-to-C and C-to-N directions is reported. The bi-directional ligation strategy makes use of thioester formation via N → S acyl shift chemistry in combination with peptide ligation reactions and was used to prepare a library of peptide oligomers ranging in molecular mass from 3.8–9.4 kDa, comprised of between 2 and 5 repeats of the MUC1 variable number tandem repeat sequence.

Graphical abstract: Synthesis of homogeneous MUC1 oligomers via a bi-directional ligation strategy

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Article information

DOI
https://doi.org/10.1039/C3OB41363B
Article type
Paper
Submitted
14 May 2013
Accepted
30 Jul 2013
First published
31 Jul 2013

Org. Biomol. Chem., 2013,11, 6090-6096

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Synthesis of homogeneous MUC1 oligomers via a bi-directional ligation strategy

D. Al Sheikha, B. L. Wilkinson, G. Santhakumar, M. Thaysen-Andersen and R. J. Payne, Org. Biomol. Chem., 2013, 11, 6090 DOI: 10.1039/C3OB41363B

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