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Nat Mater. 2003 May;2(5):324-8.

Enantiomeric interactions between nucleic acid bases and amino acids on solid surfaces.

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1
School of Chemistry, North Haugh, University of St Andrews, St Andrews, Fife KY16 9ST, UK. qc@st-and.ac.uk

Abstract

Molecular interaction between nucleic acid bases and amino acids is a fundamental process in biology. The adsorption of the molecules on surfaces provides the opportunity to study such interactions in great detail by exploiting the high-resolution imaging capabilities of scanning tunnelling microscopy (STM). The chemisorption of prochiral molecules, such as adenine, on a metal surface causes the adsorbed species to become chiral. Subsequent interactions with inherently chiral molecules may then lead to the formation of diastereoisomers, if the enantiomeric interaction process is sufficiently strong. In the case of adenine adsorption on Cu[110], the chiral adsorbates form homochiral chains. Here, we show that the adenine chain direction is fully correlated with the chirality, and that the alpha-amino acid, phenylglycine, shows a strong chiral preference in its interaction with these chains. STM images clearly demonstrate that S-phenylglycine (R-phenylglycine) binds only to chains rotated 19.5 degrees (anti-) clockwise from the [001] direction. Closer examination reveals that the enantiomeric interaction involves double rows of phenylglycine molecules and the adenine chains. This is the first observation at the molecular level of diastereoisomeric interaction, and demonstrates that STM is a powerful method for studying the details of these interactions.

PMID:
12692537
DOI:
10.1038/nmat878
[Indexed for MEDLINE]
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