(1S,2S,3R,6R)‐6‐Aminocyclohex‐4‐ene‐1,2,3‐triol (= (−)‐Conduramine B‐1) Is a Selective Inhibitor of α‐Mannosidases. Its Inhibitory Activity Is Enhanced by N‐Benzylation
(−)- and (+)-Conduramine B-1 ((−)- and (+)-5, resp.) have been derived from (+)- and (−)-7-oxabicyclo[2.2.1]hept-5-en-2-one (‘naked sugars’ of the first generation). Although (−)-5 imitates the structure of β-glucosides, it does not inhibit β-glucosidases but inhibits α-mannosidases selectively. N-Benzylation of (−)-5 improves the potency of conduramine B-1 as α-mannosidase inhibitor and also generates compounds inhibiting β-glucosidases. For instance, (−)-N-benzyl-conduramine B-1 ((−)-19a) is a competitive inhibitor of β-glucosidase from almonds (IC50 = 32 μM, Ki = 10 μM) and a weak inhibitor of α-mannosidases from jack bean (IC50 = 171 μM) and from almonds (IC50 = 225 μM) whereas (−)-N-(4-phenylbenzyl)conduramine B-1 ((−)-19g) is a good inhibitor of α-mannosidase from jack beans (IC50 = 29 μM, Ki = 4.8 μM) and a weaker inhibitor of β-glucosidase from almonds (IC50 = 32 μM, Ki = 7.8 μM) (Table 1).
Data provided are for informational purposes only. Although carefully collected, accuracy cannot be guaranteed. The impact factor represents a rough estimation of the journal's impact factor and does not reflect the actual current impact factor. Publisher conditions are provided by RoMEO. Differing provisions from the publisher's actual policy or licence agreement may be applicable.