Synthesis and Glycosidase Inhibition Study of 2‐C‐Hydroxymethyl‐ and 6‐C‐Hydroxymethyl‐Branched Piperidines from D‐Glucose Using Ene‐Yne Metathesis as a Key Step. Issue 19 (19th May 2014)

• Record Type: Journal Article
• Authors: Mallick, Asadulla; Vankar, Yashwant D.
• Is Part Of: European journal of organic chemistry. Issue 19(2014)
• Page Start: 4155
• Page End: 4161
• Publication Date: 2014-05-19
• Subjects: Carbohydrates -- Azasugars -- Metathesis -- Inhibitors; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402142
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Two polyhydroxylated piperidine‐based 2‐ C ‐hydroxymethyl‐branched analogues ofL ‐1‐deoxyallonojirimycin (L ‐ allo ‐DNJ) were synthesized from readily available 1, 2:5, 6‐di‐ O ‐isopropylidene‐α‐glucofuranose through an ene‐yne metathesis as the key step. The glycosidase inhibition activity of these compounds against some commercially available enzymes was examined, and the analogues were found to be very selective glycosidase inhibitors at concentrations in the range of 21–44 μM . Abstract : Piperidine‐based 2‐ C ‐hydroxymethyl‐branched analogues ofL ‐1‐deoxyallonojirimycin (L ‐ allo ‐DNJ) were synthesized from readily availableD ‐glucose by using an ene‐yne metathesis as the key step; PG = protecting group. The glycosidase inhibition activity of these compounds was studied and found to be active and very selective.