Synthesis of fluorinated analogues of N-acetyllactosamine and the study of their conformation and interactions with human galectins

Abstract: N-acetyllactosamine is an important disaccharide found in the structure of bioactive glycoproteins and glycolipids involved in cell recognition, carcinogenesis, and metastasis. In this work, a complete series of systematically fluorinated N-acetyllactosamine analogs were synthesized and studied by a comprehensive approach involving molecular modeling, X-ray structural crystallography, and nuclear magnetic resonance. Fluorination of specific positions of N-acetyllactosamine was found to significantly affect its physicochemical properties, conformational behavior, and also recognition by human galectins. The results can be used for the development of new carbohydrate-based materials or therapeutics.