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The Self‐Assembly of a Lipophilic Guanosine Nucleoside into Polymeric Columnar Aggregates: The Nucleoside Structure Contains Sufficient Information To Drive the Process towards a Strikingly Regular Polymer
Author(s) -
Mezzina Elisabetta,
Mariani Paolo,
Itri Rosangela,
Masiero Stefano,
Pieraccini Silvia,
Spada Gian Piero,
Spinozzi Francesco,
Davis Jeffery T.,
Gottarelli Giovanni
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010119)7:2<388::aid-chem388>3.0.co;2-v
Subject(s) - guanosine , alkyl , chemistry , polymer , nucleoside , crystallography , glycosidic bond , self assembly , solvent , polymer chemistry , stereochemistry , organic chemistry , biochemistry , enzyme
Lipophilic guanosine derivatives act as self‐assembled ionophores. In the presence of alkali metal ions in organic solvents, these G derivatives can form tubular polymeric structures. The molecular aggregates formed by 3′,5′‐didecanoyl‐2′‐deoxyguanosine ( 1 ) have been characterised by SANS and NMR spectroscopy. The polymer is structured as a pile of stacked G quartets held together by the alkali metal ions that occupy the column's central channel. The deoxyribose moieties, with their alkyl substituents, surround the stacked G quartets, and the nucleoside's long‐chain alkyl tails are in intimate contact with the organic solvent. In this polymeric structure, there is an amazing regularity in the rotamers around the glycosidic bond within each G quartet and in the repeat sequence of the G quartets along the columns. In hydrocarbon solvents, these columnar aggregates form lyomesophases of the cholesteric and hexagonal types.