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Cooperative face‐to‐face and edge‐to‐face aromatic interactions of tryptophan indole ring with N7‐quarternized guanine and neutral cytosine bases
Author(s) -
Ishida Toshimasa,
Tarui Mariko,
In Yasuko,
Ogiyama Michiyo,
Doi Mitsunobu,
Inoue Masatoshi
Publication year - 1993
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(93)80656-f
Subject(s) - indole test , stacking , tryptophan , guanine , cytosine , ring (chemistry) , chemistry , stereochemistry , crystallography , biochemistry , nucleotide , dna , organic chemistry , amino acid , gene
In order to investigate the effect of cytosine base upon the stacking interaction of N7‐quarternized guanine base with tryptophan indole ring, the X‐ray crystal structure of a 1:1 complex of model compounds 1 and 2 was carried out. Contrary to the expectation of the interaction of both molecules in aqueous solution, the crystal structure showed the first example of the simultaneous recognition of the Trp indole ring by guanine and cytosine bases by the coupling of the face‐to‐face and edge‐to‐face aromatic interactions, respectively.