Noncovalent Saccharide Recognition by Means of a Tetrakis(bile acid)–Porphyrin Conjugate: Selectivity, Cooperation, and Stability

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Molecular recognition of Glu, Glc 2 ‐Glc 6 and Mal 3 by a tetrakis(bile acid)–porphyrin conjugate has been studied by using ESI‐FTICR mass spectrometry. The bile acid conjugate was observed to form 1:1 noncovalent complexes with saccharides. The conjugate was found to have size‐selectivity towards saccharides with three or more glucose residues. The Glc 3 and Glc 4 also formed kinetically the most stable complexes. The electron capture dissociation (ECD) experiments revealed that in complexation of an oligosaccharide three glucose residues interact with the bile acid conjugate, whereas additional glucose residues are susceptible to fragmentation. The ECD results also showed the significance of the porphyrin centre for complexation of an intact oligosaccharide. It is obvious that the complexation of an intact sugar requires at least one bile acid side arm and the porphyrin centre.