Current Organic Chemistry

Author(s): Roman Bielski and Michal Tencer

DOI: 10.2174/138527208785161178

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Why is Ribose the Sugar Component of Nucleic Acids? New Insights into Absolute Asymmetric Synthesis and Absolute Enantioselective Separation

Page: [995 - 1003] Pages: 9

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Abstract

Consequences of a chiral influence consisting of three independent factors orienting molecules are reviewed and discussed. This influence may affect mutual orientation of reacting molecules leading to absolute asymmetric synthesis. It may also exert different orientation of opposite enantiomers relative to a flat surface which can lead to absolute enantioselective separation. Besides the obvious although not trivial possible applicability in organic synthesis, such a process, when applied to a mixture of monosaccharides may have consequences related to the formation of enantiomerically pure ribose under prebiotic conditions. It is shown that α-DL-ribopyranose is the easiest racemic monosaccharide to get separated to enantiomers.

Keywords: Asymmetric Synthesis, Ribose, Nucleic Acids, chiral, enantiomers, enantioselective separation, racemic monosaccharide, stereochemistry