Abstract
Recent studies confirm that C-H...O hydrogen bonds have many, if not all, of the spectroscopic and physical earmarks of “traditional” H-bonds. Only more recently have we come to understand that these contacts are operative not only in protein-protein recognition, but enzyme-substrate interactions (with implications for drug design), biological and nonbiological transition state stabilization and have, in some circumstances, a strength and geometric predictability to make them useful in the construction of materials and supramolecular assemblies. Forays into each of these areas have come largely due to advances in computational protocols and spectroscopic instrumentation. This review discusses the most recent findings related to the nature (i.e. strength, geometrical preferences, and spectroscopic features) and function (i.e. in supramolecular design and synthesis, conformational control, enantioselective synthesis, and biology) of C-H...O interactions in a variety of chemical and biological systems. An understanding of the key features of these interactions should promote their deployment in target areas like medicinal chemistry and materials science.
Keywords: H-bonds, enzyme-substrate interactions, spectroscopic
Current Organic Chemistry
Title: Progress Toward Understanding the Nature and Function of C-H...O Interactions
Volume: 8 Issue: 10
Author(s): Ronald K. Castellano
Affiliation:
Keywords: H-bonds, enzyme-substrate interactions, spectroscopic
Abstract: Recent studies confirm that C-H...O hydrogen bonds have many, if not all, of the spectroscopic and physical earmarks of “traditional” H-bonds. Only more recently have we come to understand that these contacts are operative not only in protein-protein recognition, but enzyme-substrate interactions (with implications for drug design), biological and nonbiological transition state stabilization and have, in some circumstances, a strength and geometric predictability to make them useful in the construction of materials and supramolecular assemblies. Forays into each of these areas have come largely due to advances in computational protocols and spectroscopic instrumentation. This review discusses the most recent findings related to the nature (i.e. strength, geometrical preferences, and spectroscopic features) and function (i.e. in supramolecular design and synthesis, conformational control, enantioselective synthesis, and biology) of C-H...O interactions in a variety of chemical and biological systems. An understanding of the key features of these interactions should promote their deployment in target areas like medicinal chemistry and materials science.
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Cite this article as:
Castellano K. Ronald, Progress Toward Understanding the Nature and Function of C-H...O Interactions, Current Organic Chemistry 2004; 8 (10) . https://dx.doi.org/10.2174/1385272043370384
DOI https://dx.doi.org/10.2174/1385272043370384 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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