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Conformer equilibria of triostin A and its conformer-specific interaction with nucleic acid bases

✍ Scribed by Yoshimasa Kyogoku; Naoki Higuchi; Mayumi Watanabe; Keiichi Kawano


Publisher
Wiley (John Wiley & Sons)
Year
1981
Tongue
English
Weight
587 KB
Volume
20
Category
Article
ISSN
0006-3525

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✦ Synopsis


Abstract

A quinoxaline antibiotic triostin A has a bicyclic octadepsipeptide structure. Proton and carbon‐13 nmr spectra showed the presence of two symmetrical conformations favoring polar and nonpolar solvents, respectively. They interconvert slowly on the nmr time scale, and this slow interconversion is due to the cooperative effects of the presence of the quinoxaline ring and the N‐methyl peptide bonds. Reversal of the chirality of the disulfide bond as the origin of the slow exchange was excluded by the presence of two conformers for S‐benzyltriostin A. Conformer 2, which favors the polar solvent, can form hydrogen‐bonded complexes with purine nucleoside derivatives in organic solvents, but conformer 1 does not. The binding sites were elucidated and a mode of interaction with DNA proposed.


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