scholarly journals New glucuronic acid donors for the modular synthesis of heparan sulfate oligosaccharides

2014 ◽  
Vol 12 (13) ◽  
pp. 2087-2098 ◽  
Author(s):  
Omkar P. Dhamale ◽  
Chengli Zong ◽  
Kanar Al-Mafraji ◽  
Geert-Jan Boons
Keyword(s):  
Heparan Sulfate ◽  
Glucuronic Acid ◽  
Building Blocks ◽  
Modular Synthesis ◽  
Heparan Sulfate Oligosaccharides

A streamlined approach has been developed for the preparation of modular disaccharide building blocks for the assembly of libraries of HS oligosaccharides that avoids postglycosylation oxidation.

scholarly journals Fluorous Supported Modular Synthesis of Heparan Sulfate Oligosaccharides

2013 ◽  
Vol 15 (2) ◽  
pp. 342-345 ◽  
Author(s):  
Chengli Zong ◽  
Andre Venot ◽  
Omkar Dhamale ◽  
Geert-Jan Boons
Keyword(s):  
Heparan Sulfate ◽  
Modular Synthesis ◽  
Heparan Sulfate Oligosaccharides

scholarly journals Modular Synthesis of Heparan Sulfate Oligosaccharides for Structure−Activity Relationship Studies

2009 ◽  
Vol 131 (47) ◽  
pp. 17394-17405 ◽  
Author(s):  
Sailaja Arungundram ◽  
Kanar Al-Mafraji ◽  
Jinkeng Asong ◽  
Franklin E. Leach ◽  
I. Jonathan Amster ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Structure Activity Relationship ◽  
Activity Relationship ◽  
Modular Synthesis ◽  
Structure Activity ◽  
Heparan Sulfate Oligosaccharides

Toward the Solid-Phase Synthesis of Heparan Sulfate Oligosaccharides: Evaluation of Iduronic Acid and Idose Building Blocks

2013 ◽  
Vol 78 (14) ◽  
pp. 6911-6934 ◽  
Author(s):  
Nerea Guedes ◽  
Pawel Czechura ◽  
Begoña Echeverria ◽  
Ada Ruiz ◽  
Olatz Michelena ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis ◽  
Iduronic Acid ◽  
Heparan Sulfate Oligosaccharides

scholarly journals Preparation of a set of selectively protected disaccharides for modular synthesis of heparan sulfate fragments: toward the synthesis of several O-sulfonated [β-D-GlcUA-(1→4)-β-D-GlcNAc]OPr types

2005 ◽  
Vol 3 (4) ◽  
pp. 803-829 ◽  
Author(s):  
Hammed Hassan
Keyword(s):  
Heparan Sulfate ◽  
Building Blocks ◽  
Protecting Groups ◽  
Hydroxyl Group ◽  
Hydroxyl Groups ◽  
Allyl Ethers ◽  
Modular Synthesis ◽  
Stereocontrolled Synthesis ◽  
Benzyl Ethers ◽  
Free Hydroxyl

AbstractA concise method for a stereocontrolled synthesis of a set of selectively protected disaccharides is reported. Coupling of the donor 11 onto acceptors 23 and 24, promoted by trimethylsilyl triflate-N-iodosuccinimide (TMSOTf-NIS), generated the disaccharides 25 and 26. Under typical conditions, condensation of the fully protected donor 12 onto acceptors 23 and 24 produced the disaccharides 27 and 28. The building blocks 25–28 were prepared in moderate yields having exclusive β-stereoselectivity. A unique pattern of protecting groups distinguished clearly between positions to be sulfated and functional groups remaining as free hydroxyl groups. Acetyl and/or levulinoyl esters temporarily protected the positions to be sulfated, while benzyl ethers were used for permanent protection. The anomeric positions were protected as allyl ethers, whereas the 4′-positions were masked as p-methoxybenzyl (PMB) ethers. The orthogonality of the PMB and allyl groups can then be used for further elongation of the chain by recurrent deprotection and activation steps. The hydroxyl group, OH-6, of glucosamine moieties was protected as a TBDPS ether to avoid oxidation. A five-step deprotection/sulfonation sequence was applied to the disaccharide 27 to generate the corresponding sulfated [β-D-GlcUA-2-OSO3Na-(1→4)-β-D-Glc pNAc]-(1→O-Pro) 34.

scholarly journals Using automated glycan assembly (AGA) for the practical synthesis of heparan sulfate oligosaccharide precursors

2019 ◽  
Vol 17 (7) ◽  
pp. 1817-1821 ◽  
Author(s):  
Darshita Budhadev ◽  
Karinna Saxby ◽  
Julia Walton ◽  
Gideon Davies ◽  
Peter C. Tyler ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Building Blocks ◽  
Practical Synthesis

Herein we report synthesis of complex heparan sulfate oligosaccharide precursors by automated glycan assembly using disaccharide donor building blocks.

Sign in / Sign up

Export Citation Format

Share Document