Enzymes in Organic Synthesis: Aldolase-Mediated Synthesis of Iminocyclitols and Novel Heterocycles

摘要

The preparation and evaluation of carbohydrate mimics in which the endocyclic oxygen is replaced with nitrogen began with the syntheses of 5-acctamido-5-deoxy-D-xylopiperidinose in the 1960s by Paulsen,Jones,and Hanessian as purely academic exercises.The substitution of nitrogen for oxygen produces metabolically inert iminocyclitols (also referred to as iminosugars or azasugars) that typically bind to carbohydrate-processing enzymes such as glycosidases.