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

作者：Kalenius Elina^*; Koivukorpi Juha; Kolehmainen Erkki; Vainiotalo Pirjo

来源：European Journal of Organic Chemistry, 2010, 2010(6): 1052-1058.

DOI：10.1002/ejoc.200901168

• Molecular recognition
• Saccharide recognition
• Porphyrin conjugates
• Noncovalent interactions
• Mass spectrometry

Molecular recognition of Glu, Glc(2)-Glc(6) and Mal(3) by a tetrakis(bile acid)-porphyrin conjugate has been studied by using EST-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.

• 出版日期2010-2