Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks |
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| Authors: | Lisa Tanzi Marina Simona Robescu Sara Marzatico Teresa Recca Yongmin Zhang Marco Terreni Teodora Bavaro |
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| Institution: | 1.Department of Drug Sciences, University of Pavia, viale Taramelli 12, I-27100 Pavia, Italy; (L.T.); (M.S.R.); (S.M.); (M.T.);2.Institut Parisien de Chimie Moléculaire, Sorbonne Université, CNRS, UMR 8232, 4 Place Jussieu, 75005 Paris, France;3.Centro Grandi Strumenti, University of Pavia, via Bassi 21, I-27100 Pavia, Italy; |
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| Abstract: | Regioselective deprotection of acetylated mannose-based mono- and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells. |
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| Keywords: | acetyl xylan esterase Candida rugosa lipase enzyme immobilization enzymatic hydrolysis monosaccharides disaccharides mannose-based oligosaccharides |
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