Dimethyl (1S,2S,4S,5S)-4-allyloxy-5-(α-mannosyloxy)cyclohexane-1,2- dicarboxylate (3) was designed as a structural mimic of α(1,2)mannobioside (1). Its synthesis and structural analysis by NMR spectroscopy and molecular modelling are described. The results show that 3, like 1, populates two low-energy conformations - stacked (S) and extended (E) - that are in fast dynamic equilibrium around the glycosidic linkage. Thus, the data confirm the expectation that the pseudo-disaccharide can be used as a structural mimic of mannobioside. The mannosidase stability of 3 was found to be significantly higher (sixfold) than that of natural mannobioside. This is a very useful feature of this mimic and is encouraging for its future development.
Synthesis, Conformational Studies and Mannosidase Stability of a Mimic of 1,2-Mannobioside / S. Mari, H. Posteri, G. Marcou, D. Potenza, F. Micheli, F. J. Cañada, J. Jimenez-Barbero,A. Bernardi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - :24(2004), pp. 5119-5125. [10.1002/ejoc.200400520]
Synthesis, Conformational Studies and Mannosidase Stability of a Mimic of 1,2-Mannobioside
S. MariPrimo
;H. PosteriSecondo
;D. Potenza;A. BernardiUltimo
2004
Abstract
Dimethyl (1S,2S,4S,5S)-4-allyloxy-5-(α-mannosyloxy)cyclohexane-1,2- dicarboxylate (3) was designed as a structural mimic of α(1,2)mannobioside (1). Its synthesis and structural analysis by NMR spectroscopy and molecular modelling are described. The results show that 3, like 1, populates two low-energy conformations - stacked (S) and extended (E) - that are in fast dynamic equilibrium around the glycosidic linkage. Thus, the data confirm the expectation that the pseudo-disaccharide can be used as a structural mimic of mannobioside. The mannosidase stability of 3 was found to be significantly higher (sixfold) than that of natural mannobioside. This is a very useful feature of this mimic and is encouraging for its future development.Pubblicazioni consigliate
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