Modulation of an n→π* interaction with α-fluoro groups.

Authors:
Amit Choudhary
Amit Choudhary
University of Wisconsin-Madison
United States
Charles G Fry
Charles G Fry
University of Wisconsin-Madison
United States
Ronald T Raines
Ronald T Raines
University of Wisconsin-Madison
United States

ARKIVOC 2010 Jul;2010:251-262

Noncovalent interactions play an essential role in biological and chemical processes. In the main chain of common protein secondary structures, the lone pair (n) of a carbonyl oxygen is delocalized into the antibonding orbital (π*) of the subsequent carbonyl group. Herein, experimental and computational data reveal that this n→π* interaction can be attenuated by the inductive electron withdrawal of one or two α-fluoro groups in the donor. The steric effect of three α-fluoro groups, however, overcomes the inductive withdrawal. These data evoke a means to modulate the n→π* interaction in peptides, proteins, and other systems.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107012PMC

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July 2010
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