87419-91-8Relevant academic research and scientific papers
Synthesis of 4a-Carba-d-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases
Zaji?ková, Mária,Monco?, Ján,?esták, Sergej,Kóňa, Juraj,Koó?, Miroslav,Bella, Maro?
, p. 1114 - 1124 (2019/01/24)
A synthetic approach to 4a-carba-d-lyxofuranose derivatives starting from d-lyxose is described. The protected 4a-carba-β-d-lyxofuranose was employed as the key intermediate for the synthesis of 4a-carba-d-lyxofuranose derivatives including novel 1-amino-1-deoxy-4a-carba-d-lyxofuranoses. Synthesized 4a-carba-d-lyxofuranoses were evaluated as inhibitors of GH38 α-mannosidases, namely, the Golgi (GMIIb) and lysosomal (LManII) α-mannosidases from Drosophila melanogaster and commercial Jack bean α-mannosidase (JBMan) from Canavalia ensiformis. The biochemical evaluation revealed that only 1-amino-1-deoxy-4a-carba-β-d-lyxofuranose exhibited reasonable inhibitory activity against GMIIb (IC50 = 200 μm). In addition, the results of biological evaluation were discussed by means of molecular modelling.
