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2005
Antibiotics
U 1200
03- 208
New DNA Binding Ligands as a Model of Chromomycin A3. — The trisaccharide
part of chromomycin A3 is replaced with a hexyl group to mimic the trisaccharide chain,
which seems to be responsible for the formation of Mg2+-coordinated dimers. The synthesis of model compounds (XI) and (XII) includes the construction of a peri-hydroxy
aromatic skeleton by a molecular-sieves-catalyzed [4 + 2] cycloaddition of homophthalic anhydride derivative (III) and α-sulfinyl-substituted cyclohexenone (VII). The
hexyl chain is responsible for the formation of dimeric complexes of model ligands (XI)
and (XII) with Mg2+. Also, DNA binding experiments indicate that the alkyl chain of
these compounds plays a key role for Mg2+-mediated DNA binding. The binding properties are independent of the stereospecific outcome of the ligands. — (IMOTO, S.;
HARUTA, Y.; WATANABE, K.; SASAKI*, S.; Bioorg. Med. Chem. Lett. 14 (2004)
19, 4855-4859; Grad. Sch. Pharm. Sci., Kyushu Univ., Higashi, Fukuoka 812, Japan;
Eng.) — H. Hoennerscheid
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