SYNTHESIS OF 1,5-DIDEOXY-3-O-(ALPHA-D-MANNOPYRANOSYL)-1,5-IMINO-D-MANNITOL AND 1,5-DIDEOXY-3-O-(ALPHA-D-GLUCOPYRANOSYL)-1,5-IMINO-D-MANNITOL - POWERFUL INHIBITORS OF ENDOMANNOSIDASE

The synthesis and conformations of 3-O-methylDMJ, 3-O-(alpha-D-glucopyranosyl)-DMJ (Glcalpha1,3DMJ), and 3-O-(alpha-D-mannopyranosyl)-DMJ (Manalpha1,3DMJ) are described. Manalpha1,3DMJ and Glcalpha1,3DMJ are shown to be very powerful inhibitors of an endomannosidase. The potential use of these compounds in both probing the pathways of N-linked glycoprotein processing and in the chemotherapy of some viral diseases is discussed.