Dynamic combinatorial chemistry at the phospholipid bilayer interface

Mansfeld, Friederike M., Au-Yeung, Ho Yu, Sanders, Jeremy K. M. and Otto, Sijbren (2010) Dynamic combinatorial chemistry at the phospholipid bilayer interface. Journal of Systems Chemistry, 1 12: 1-13. doi:10.1186/1759-2208-1-12

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Author Mansfeld, Friederike M.
Au-Yeung, Ho Yu
Sanders, Jeremy K. M.
Otto, Sijbren
Title Dynamic combinatorial chemistry at the phospholipid bilayer interface
Journal name Journal of Systems Chemistry   Check publisher's open access policy
ISSN 1759-2208
Publication date 2010-09-08
Sub-type Article (original research)
DOI 10.1186/1759-2208-1-12
Open Access Status DOI
Volume 1
Issue 12
Start page 1
End page 13
Total pages 13
Place of publication London, United Kingdom
Publisher BioMed Central
Language eng
Formatted abstract
Background: Molecular recognition at the environment provided by the phospholipid bilayer interface plays an important role in biology and is subject of intense investigation. Dynamic combinatorial chemistry is a powerful approach for exploring molecular recognition, but has thus far not been adapted for use in this special microenvironment.

Results:
Thioester exchange was found to be a suitable reversible reaction to achieve rapid equilibration of dynamic combinatorial libraries at the egg phosphatidyl choline bilayer interface. Competing thioester hydrolysis can be minimised by judicial choice of the structure of the thioesters and the experimental conditions. Comparison of the library compositions in bulk solution with those in the presence of egg PC revealed that the latter show a bias towards the formation of library members rich in membrane-bound building blocks. This leads to a shift away from macrocyclic towards linear library members.

Conclusions:
The methodology to perform dynamic combinatorial chemistry at the phospholipid bilayer interface has been developed. The spatial confinement of building blocks to the membrane interface can shift the ringchain equilibrium in favour of chain-like compounds. These results imply that interfaces may be used as a platform to direct systems to the formation of (informational) polymers under conditions where small macrocycles would dominate in the absence of interfacial confinement.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Chemistry and Molecular Biosciences
 
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Created: Tue, 20 Sep 2011, 16:55:36 EST by Friederike Mansfeld on behalf of School of Chemistry & Molecular Biosciences