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Influence of β ‐Alanine on Hairpin Polyamide Orientation in the DNA Minor Groove
Author(s) -
Rucker Victor C.,
Melander Christian,
Dervan Peter B.
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390148
Subject(s) - antiparallel (mathematics) , chemistry , minor groove , stereochemistry , dna , alanine , polyamide , orientation (vector space) , pyrrole , crystallography , amino acid , biochemistry , organic chemistry , geometry , physics , mathematics , quantum mechanics , magnetic field
Antiparallel polyamides containing 1 H ‐pyrrole, 1 H ‐imidazole, and 3‐hydroxy‐1 H ‐pyrrole amino acids display a preference for minor‐groove binding oriented NC with respect to the 5′‐3′ direction of the DNA helix. We find that replacement of a central Py/Py pair with a β / β pair within a ten‐ring hairpin relaxes the orientation preference and, for some DNA sequences, causes the polyamide to prefer the opposite CN orientation. Substitution of the achiral γ ‐aminobutanoic acid ( γ ) with either ( R )(or S )‐2‐(acetylamino)‐4‐aminobutanoic acid moderates the orientation preference of the 2‐ β ‐2‐hairpin.