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Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks

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,...

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Autores principales: Tanzi, Lisa, Robescu, Marina Simona, Marzatico, Sara, Recca, Teresa, Zhang, Yongmin, Terreni, Marco, Bavaro, Teodora
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7730743/
https://www.ncbi.nlm.nih.gov/pubmed/33297422
http://dx.doi.org/10.3390/molecules25235764
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author Tanzi, Lisa
Robescu, Marina Simona
Marzatico, Sara
Recca, Teresa
Zhang, Yongmin
Terreni, Marco
Bavaro, Teodora
author_facet Tanzi, Lisa
Robescu, Marina Simona
Marzatico, Sara
Recca, Teresa
Zhang, Yongmin
Terreni, Marco
Bavaro, Teodora
author_sort Tanzi, Lisa
collection PubMed
description 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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spelling pubmed-77307432020-12-12 Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks Tanzi, Lisa Robescu, Marina Simona Marzatico, Sara Recca, Teresa Zhang, Yongmin Terreni, Marco Bavaro, Teodora Molecules Article 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. MDPI 2020-12-07 /pmc/articles/PMC7730743/ /pubmed/33297422 http://dx.doi.org/10.3390/molecules25235764 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tanzi, Lisa
Robescu, Marina Simona
Marzatico, Sara
Recca, Teresa
Zhang, Yongmin
Terreni, Marco
Bavaro, Teodora
Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks
title Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks
title_full Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks
title_fullStr Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks
title_full_unstemmed Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks
title_short Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks
title_sort developing a library of mannose-based mono- and disaccharides: a general chemoenzymatic approach to monohydroxylated building blocks
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7730743/
https://www.ncbi.nlm.nih.gov/pubmed/33297422
http://dx.doi.org/10.3390/molecules25235764
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