909900-65-8

Upstream product

• 17277-59-7 methyl (benzylthio)acetate 
• 2450-71-7 Propargylamine 
• 103-46-8 S-benzylmercaptoacetic acid 
• 100-53-8 phenylmethanethiol 
• 173208-24-7 2-bromo-N-(prop-2-ynyl)acetamide 

Downstream Products

• 909900-66-9 1-N-(3,4,6-tri-O-acetyl-2-deoxy-2-N-deoxy-N-acetyl-β-D-glucopyranosylamido)-4-(N'-methylidenyl-2'-thiobenzylacetamido)-4,5-anhydro-triazole 

Relevant academic research and scientific papers

A combinatorial approach towards the synthesis of non-hydrolysable triazole-iduronic acid hybrid inhibitors of human α-l-iduronidase: Discovery of enzyme stabilizers for the potential treatment of MPSI

Preparation of substituent-diverse, triazole-iduronic acid hybrid molecules by click reaction of an azido iduronic acid derivative with randomly chosen alkynes is described. Library members were screened for their ability to inhibit α-l-iduronidase, and hit molecules and analogues were then investigated for their ability to stabilize rh-α-IDUA in a thermal denaturation study. This work resulted in the discovery of the first small molecules that can be used to stabilize exogenous rh-α-IDUA protein in vitro.

Three-component chemoenzymatic synthesis of amide ligated 1,2,3-triazoles

CAL-B (Candida antarctica lipase B) immobilized on an acrylic resin (Novozyme 435) smoothly catalyzes the aminolysis of methyl esters with propargyl amine furnishing propargyl amides. In the same reaction vessel these propargyl derivatives are consecutively transformed into amide ligated 1,2,3-triazoles in a Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction in good to excellent yields.

A novel neoglycopeptide linkage compatible with native chemical ligation

The straightforward synthesis of a novel class of neoglycopeptide and its fusion with a larger peptide thioester using sequential chemoselective ligations is described. The Royal Society of Chemistry 2006.