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Sci. STKE, 3 May 2005
Vol. 2005, Issue 282, p. tw168
[DOI: 10.1126/stke.2822005tw168]

EDITORS' CHOICE

BIOCHEMISTRY Linked Rings from a Library

Combinatorial chemical synthesis can rapidly generate many different compounds, but they often share an underlying structure that represents a fairly small region of chemical space. Lam et al. used a dynamic combinatorial approach to discover a surprisingly elaborate structure for binding the acetylcholine neurotransmitter. The authors added synthetic dipeptides to an acetylcholine solution under conditions allowing reversible coupling. At equilibrium, the predominant structure that had self-assembled as a receptor was a pair of linked 42-membered rings, each a trimer of the dipeptide building blocks. This catenane molecule was isolated in 65% yield and showed a 100 nanomolar affinity for the neurotransmitter.

R. T. S. Lam, A. Belenguer, S. L. Roberts, C. Naumann, T. Jarrosson, S. Otto, J. K. M. Sanders, Amplification of acetylcholine-binding catenanes from dynamic combinatorial libraries. Science 308, 667-669 (2005). [Abstract] [Full Text]

Citation: Linked Rings from a Library. Sci. STKE 2005, tw168 (2005).


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