Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker

A concise synthetic route to an immunomodulatory pentasaccharide, lacto-N-fucopentaose III (1) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio- and stereoselective glycosylations for the construction of disaccharide 10 a...

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Autores principales: Zhang, Junfeng, Zou, Lu, Lowary, Todd L
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2013
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3775522/
https://www.ncbi.nlm.nih.gov/pubmed/24551556
http://dx.doi.org/10.1002/open.201300024
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author Zhang, Junfeng
Zou, Lu
Lowary, Todd L
author_facet Zhang, Junfeng
Zou, Lu
Lowary, Todd L
author_sort Zhang, Junfeng
collection PubMed
description A concise synthetic route to an immunomodulatory pentasaccharide, lacto-N-fucopentaose III (1) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio- and stereoselective glycosylations for the construction of disaccharide 10 and pentasaccharide 12, a Birch reduction for deprotection of benzyl ethers, and a UV-promoted radical addition of a thiol to an alkene for modification of the aglycone.
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spelling pubmed-37755222014-02-18 Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker Zhang, Junfeng Zou, Lu Lowary, Todd L ChemistryOpen Full Papers A concise synthetic route to an immunomodulatory pentasaccharide, lacto-N-fucopentaose III (1) and its corresponding human serum albumin conjugate, is described. Key transformations of the strategy include two highly regio- and stereoselective glycosylations for the construction of disaccharide 10 and pentasaccharide 12, a Birch reduction for deprotection of benzyl ethers, and a UV-promoted radical addition of a thiol to an alkene for modification of the aglycone. WILEY-VCH Verlag 2013-08 2013-07-11 /pmc/articles/PMC3775522/ /pubmed/24551556 http://dx.doi.org/10.1002/open.201300024 Text en © 2013 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. http://creativecommons.org/licenses/by/2.5/ Re-use of this article is permitted in accordance with the Creative Commons Deed, Attribution 2.5, which does not permit commercial exploitation.
spellingShingle Full Papers
Zhang, Junfeng
Zou, Lu
Lowary, Todd L
Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker
title Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker
title_full Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker
title_fullStr Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker
title_full_unstemmed Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker
title_short Synthesis of the Tolerance-Inducing Oligosaccharide Lacto-N-Fucopentaose III Bearing an Activated Linker
title_sort synthesis of the tolerance-inducing oligosaccharide lacto-n-fucopentaose iii bearing an activated linker
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3775522/
https://www.ncbi.nlm.nih.gov/pubmed/24551556
http://dx.doi.org/10.1002/open.201300024
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