The enzymatic modification of glucosamine (GlcN) and its derivatives have a keen interest for researchers due to the natural abundance of its bio-sourced such as chitin. The recent progress for understanding the role of glucosamine based on various novel approaches for enzymatic synthesis in the field of medicinal chemistry and food supplements. These developments led to improve chemo-selective protection and/or deprotection of amino-sugar during chainenhancement and allow the simultaneous regioselective reaction of functionally relevant acetyl, phosphate, or sulfate groups. In this review, we give an overview of current strategies on the synthesis of therapeutically relevant glucosaminecontaining derivatives.