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Chemo-enzymatic Synthesis of Clickable Xylo-oligosaccharide Monomers From Hardwood 4-O-Methylglucuronoxylan

Chemo-enzymatic Synthesis of Clickable Xylo-oligosaccharide Monomers From Hardwood 4-O-Methylglucuronoxylan

Benjamin MacCormick, Thu V Vuong, Emma R Master

Biomacromolecules. 2018 Feb 12;19(2):521-530.

PMID: 29338223

Abstract:

A chemo-enzymatic pathway was developed to transform 4-O-methylglucuronic acid (MeGlcpA) containing xylo-oligosaccharides from beechwood into clickable monomers capable of polymerizing at room temperature and in aqueous conditions to form unique polytriazoles. While the gluco-oligosaccharide oxidase (GOOX) from Sarocladium strictum was used to oxidize C6-propargylated oligosaccharides, the acid-amine coupling reagents 1-ethyl-3-(3-(dimethylamino)propyl) carbodiimide (EDAC) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) were employed and compared for their ability to append click functionalities to carboxylic acid groups of enzyme-treated oligosaccharides. While DMT-MM was a superior coupling reagent for this application, a triazine side product was observed during C-1 amidation. Resulting bifunctional xylo-oligosaccharide monomers were polymerized using a Cu(I) catalyst, forming a soft gel which was characterized by 1H NMR, confirming the triazole product.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP56512493	4-(Dimethylamino)azobenzene-4′-sulfonyl chloride		56512-49-3	Price

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