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Synlett 2017; 28(01): 103-107
DOI: 10.1055/s-0036-1589709
DOI: 10.1055/s-0036-1589709
cluster
Mechanism of Building Block Exchange in Stacks of Self-Replicating Macrocycles
Further Information
Publication History
Received: 30 September 2016
Accepted after revision: 07 November 2016
Publication Date:
23 November 2016 (online)
![](https://www.thieme-connect.de/media/synlett/201701/lookinside/thumbnails/st-2016-s0657-c_10-1055_s-0036-1589709-1.jpg)
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.
Key words
self-replication - self-assembly - exchange - supramolecular polymers - dynamic combinatorial chemistry - systems chemistrySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1589709.
- Supporting Information
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References and Notes
- 1a Ghosh I, Chmielewski J. Curr. Opin. Chem. Biol. 2004; 8: 640
- 1b Paul N, Joyce GF. Curr. Opin. Chem. Biol. 2004; 8: 634
- 1c Patzke V, von Kiedrowski G. ARKIVOC 2007; (v): 293
- 1d Vidonne A, Philp D. Eur. J. Org. Chem. 2009; 593
- 1e Kassianidis E, Pearson RJ, Wood EA, Philp D. Faraday Discuss. 2010; 145: 235
- 1f Bissette AJ, Fletcher SP. Angew. Chem. Int. Ed. 2013; 52: 12800
- 1g Clixby G, Twyman L. Org. Biomol. Chem. 2016; 14: 4170
- 2a Ruiz-Mirazo K, Briones C, de la Escosura A. Chem. Rev. 2014; 114: 285
- 2b Pross A. What Is Life? How Chemistry Becomes Biology. Oxford University Press; Oxford: 2012
- 3a del Amo V, Philp D. Chem. Eur. J. 2010; 16: 13304
- 3b Moulin E, Giuseppone N. Top. Curr. Chem. 2012; 322: 87
- 3c Otto S. Acc. Chem. Res. 2012; 45: 2200
- 3d del Arno V, Slawin AM. Z, Philp D. Org. Lett. 2008; 10: 4589
- 3e Sadownik JW, Philp D. Angew. Chem. Int. Ed. 2008; 47: 9965
- 3f Turega SM, Lorenz C, Sadownik JW, Philp D. Chem. Commun. 2008; 4076
- 3g Xu S, Giuseppone N. J. Am. Chem. Soc. 2008; 130: 1826
- 3h Nguyen R, Allouche L, Buhler E, Giuseppone N. Angew. Chem. Int. Ed. 2009; 48: 1093
- 3i Mukherjee R, Cohen-Luria R, Wagner N, Ashkenasy GA. Angew. Chem. Int. Ed. 2015; 54: 12452
-
4a Carnall JM. A, Waudby CA, Belenguer AM, Stuart MC. A, Peyralans JJ. P, Otto S. Science 2010; 327: 1502
- 4b Malakoutikhah M, Peyralans JJ. P, Colomb-Delsuc M, Fanlo-Virgos H, Stuart MC. A, Otto S. J. Am. Chem. Soc. 2013; 135: 18406
-
4c Colomb-Delsuc M, Mattia E, Sadownik JW, Otto S. Nat. Commun. 2015; 6: 7427
- 4d Leonetti G, Otto S. J. Am. Chem. Soc. 2015; 137: 2067
- 4e Sadownik JW, Mattia E, Nowak P, Otto S. Nat. Chem. 2016; 8: 264
- 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.
- 6 da Silva RM. P, van der Zwaag D, Albertazzi L, Lee SS, Meijer EW, Stupp SI. Nat. Commun. 2016; 7: 11561
- 7 Pal A, Malakoutikhah M, Leonetti G, Tezcan M, Colomb-Delsuc M, Nguyen VD, van der Gucht J, Otto S. Angew. Chem. 2015; 54: 7852
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