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Regioselective deprotection of monosaccharide bearing thiocyanomethyl group at the anomeric position monitored by reversed‐phase HPLC method

Abstract

In the current work, investigation and development of a chemo‐enzymatic approach for the synthesis of neo‐glycoproteins have been studied. This strategy is based on the regioselective enzymatic hydrolysis of peracetylated monosaccharide, functionalized in the anomeric position (C1) as 1‐thio‐(S‐cyanomethyl) group, a precursor of the 2‐ iminomethoxyethyl thioglycosides‐linker for protein glycosilation, catalyzed by immobilized enzymes to obtain selectively monodeprotected compounds. The use of this activation in C1 is the most frequently used strategy for glycoprotein preparation. The selected biocatalysts are the lipase from Candida rugosa and the acetyl xylan esterase from Bacillus pumilus. A reversed‐phase high‐performance liquid‐chromatographic (HPLC) method for monitoring the regioselective deprotection reaction has been developed. The developed HPLC method was used as fingerprints to follow the hydrolysis of substrate 1 to substrate 1a and to determine its purity and yield. Moreover, the obtained compound was further purified by flash chromatography. The obtained compound 1a was further characterized using 1H, 13C NMR, COZY and HMBC. The resulting product can be used as intermediate for the preparation of di‐ and more complex oligosaccharides aimed at protein conjugation.

Authors:   Qais Abualassal, Khaldun M. Al Azzam, Jamal A. Jilani
Journal:   Biomedical Chromatography
Year:   2016
Pages:   n/a
DOI:   10.1002/bmc.3699
Publication date:   11-Feb-2016
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