Observation of CH⋅⋅⋅π Interactions between Methyl and Carbonyl Groups in Proteins
نویسندگان
چکیده
منابع مشابه
Orthogonal dipolar interactions between amide carbonyl groups.
Orthogonal dipolar interactions between amide C=O bond dipoles are commonly found in crystal structures of small molecules, proteins, and protein-ligand complexes. We herein present the experimental quantification of such interactions by employing a model system based on a molecular torsion balance. Application of a thermodynamic double-mutant cycle allows for the determination of the increment...
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Noncovalent interactions define and modulate biomolecular structure, function, and dynamics. In many protein secondary structures, an intimate interaction exists between adjacent carbonyl groups of the main-chain amide bonds. As this short contact contributes to the energetics of protein conformational stability as well as protein-ligand interactions, understanding its nature is crucial. The in...
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Electronic delocalization, a central concept in organic chemistry, is being invoked increasingly in biological contexts [1–3]. We have discovered a non-covalent interaction in proteins, termed the n→π* interaction, in which the lone pair (n) of the oxygen (Oi–1) of a peptide bond overlaps with the antibonding orbital (π*) of the carbonyl group (C′i=Oi) of the subsequent peptide bond (Figure 1A,...
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n→π* Interactions Engender Chirality in Carbonyl Groups
An n→π* interaction stems from the delocalization of the electron pair (n) of a donor group into the antibonding orbital (π*) of a carbonyl group. Crystallographic analyses of five pairs of diastereoisomers demonstrate that an n→π* interaction can induce chirality in an otherwise planar, prochiral carbonyl group. Thus, a subtle delocalization of electrons can have stereochemical consequences.
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ژورنال
عنوان ژورنال: Angewandte Chemie
سال: 2017
ISSN: 0044-8249
DOI: 10.1002/ange.201702626