Synlett 2017; 28(01): 103-107
DOI: 10.1055/s-0036-1589709
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© Georg Thieme Verlag Stuttgart · New York

Mechanism of Building Block Exchange in Stacks of Self-Replicating Macrocycles

Elio Mattia
University of Groningen, Centre for Systems Chemistry, Stratingh Institute, Nijenborgh 4, 9747 AG Groningen, The Netherlands   eMail: s.otto@rug.nl
,
Asish Pal
University of Groningen, Centre for Systems Chemistry, Stratingh Institute, Nijenborgh 4, 9747 AG Groningen, The Netherlands   eMail: s.otto@rug.nl
,
Giulia Leonetti
University of Groningen, Centre for Systems Chemistry, Stratingh Institute, Nijenborgh 4, 9747 AG Groningen, The Netherlands   eMail: s.otto@rug.nl
,
Sijbren Otto*
University of Groningen, Centre for Systems Chemistry, Stratingh Institute, Nijenborgh 4, 9747 AG Groningen, The Netherlands   eMail: s.otto@rug.nl
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Publikationsverlauf

Received: 30. September 2016

Accepted after revision: 07. November 2016

Publikationsdatum:
23. November 2016 (online)


Abstract

Self-replicating molecules containing labile reversible covalent bonds are becoming increasingly topical. Yet their robustness to component exchange and the threat of loss of information has received very little attention. We show here that supramolecular interactions can efficiently protect self-replicating molecules from otherwise rapid component exchange.

Supporting Information

 
  • References and Notes


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  • 5 Supramolecular block copolymers were obtained starting with the preparation of 500 μL of a 3.8 mM solution of unlabeled monomers 1 (in 50 mM pH 8.1 potassium borate buffer) and allowing this solution to oxidize (while stirring in an HPLC vial (12 × 32 mm) tightly closed with Teflon-lined snap caps using a Teflon-coated magnetic stirrer bar (5 × 2 mm) at 1200 rpm) resulting in the formation of hexamers 1 6. These were brought to the appropriate stirring rate and 500 μL of a 3.8 mM solution of labeled building blocks 1* were added. Over the course of 2 d, labeled hexamers 1* 6 grow on the previously existing 1 6 fibers.
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