Origin of slow conformer conversion of triostin A and interaction ability with nucleic acid bases

The n.m.r. pattern of triostin A in weakly polar solvents was explained by the presence of two symmetrical conformers. Its S-benzyl derivative still shows the n.m.r. pattern of two conformers, while des-N-tetramethyltriostin A, which lacks the N-methyl groups, gives one conformer. Therefore the slow...

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Bibliographic Details
Published inInternational journal of peptide and protein research Vol. 21; no. 5; p. 541
Main Authors Higuchi, N, Kyogoku, Y, Shin, M, Inouye, K
Format Journal Article
LanguageEnglish
Published Denmark 01.05.1983
Subjects
Adenosine - analysis
Chemical Phenomena
Chemistry
Guanosine - analysis
Magnetic Resonance Spectroscopy
Molecular Conformation
Nucleic Acids
Quinoxalines
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Summary:The n.m.r. pattern of triostin A in weakly polar solvents was explained by the presence of two symmetrical conformers. Its S-benzyl derivative still shows the n.m.r. pattern of two conformers, while des-N-tetramethyltriostin A, which lacks the N-methyl groups, gives one conformer. Therefore the slow interconversion of two conformers arises from the cis-trans isomerization of the N-methyl peptide bonds, but not from the reversal of the chirality around the S-S bond. Only one of the two conformers of triostin A interacts with adenosine and guanosine derivatives. Des-N-tetramethyltriostin A can also interact with the purine nucleosides, but more preferentially with the adenosine derivative.
ISSN:0367-8377
DOI:10.1111/j.1399-3011.1983.tb02681.x