scholarly journals Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly

2019 ◽  
Vol 58 (51) ◽  
pp. 18577-18583 ◽  
Author(s):  
Nitin J. Pawar ◽  
Lei Wang ◽  
Takuya Higo ◽  
Chandrabali Bhattacharya ◽  
Pavan K. Kancharla ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Building Blocks

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.

Assembly of glycoamino acid building blocks: a new strategy for the straightforward synthesis of heparan sulfate mimics

2018 ◽  
Vol 54 (95) ◽  
pp. 13455-13458 ◽  
Author(s):  
Julia Revuelta ◽  
Roberto Fuentes ◽  
Laura Lagartera ◽  
María José Hernáiz ◽  
Agatha Bastida ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Building Blocks ◽  
New Class ◽  
New Strategy

We report on a new class of linear heparan sulfate mimics prepared by the assembly of glycoaminoacid building blocks.

scholarly journals Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly

2019 ◽  
Vol 131 (51) ◽  
pp. 18750-18756
Author(s):  
Nitin J. Pawar ◽  
Lei Wang ◽  
Takuya Higo ◽  
Chandrabali Bhattacharya ◽  
Pavan K. Kancharla ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Building Blocks

scholarly journals Heparan Sulfate Structure Affects Autophagy, Lifespan, Responses to Oxidative Stress, and Cell Degeneration in Drosophila parkin Mutants

2019 ◽  
Vol 10 (1) ◽  
pp. 129-141 ◽  
Author(s):  
Claire Reynolds-Peterson ◽  
Jie Xu ◽  
Na Zhao ◽  
Casey Cruse ◽  
Brandon Yonel ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Flight Muscle ◽  
Cell Loss ◽  
Building Blocks ◽  
Cell Types ◽  
Cell Degeneration ◽  
Link Type ◽  
Molecular Building Blocks ◽  
Modified Proteins

Autophagy is a catabolic process that provides cells with energy and molecular building blocks during nutritional stress. Autophagy also removes misfolded proteins and damaged organelles, a critical mechanism for cellular repair. Earlier work demonstrated that heparan sulfate proteoglycans, an abundant class of carbohydrate-modified proteins found on cell surfaces and in the extracellular matrix, suppress basal levels of autophagy in several cell types during development in Drosophila melanogaster. In studies reported here, we examined the capacity of heparan sulfate synthesis to influence events affected by autophagy, including lifespan, resistance to reactive oxygen species (ROS) stress, and accumulation of ubiquitin-modified proteins in the brain. Compromising heparan sulfate synthesis increased autophagy-dependent processes, evident by extended lifespan, increased resistance to ROS, and reduced accumulation of ubiquitin-modified proteins in the brains of ROS exposed adults. The capacity of altering heparan sulfate biosynthesis to protect cells from injury was also evaluated in two different models of neurodegeneration, overexpression of Presenilin and parkin mutants. Presenilin overexpression in the retina produces cell loss, and compromising heparan sulfate biosynthesis rescued retinal patterning and size abnormalities in these animals. parkin is the fly homolog of human PARK2, one of the genes responsible for juvenile onset Parkinson’s Disease. Parkin is involved in mitochondrial surveillance and compromising parkin function results in degeneration of both flight muscle and dopaminergic neurons in Drosophila. Altering heparan sulfate biosynthesis suppressed flight muscle degeneration and mitochondrial dysmorphology, indicating that activation of autophagy-mediated removal of mitochondria (mitophagy) is potentiated in these animals. These findings provide in vivo evidence that altering the levels of heparan sulfate synthesis activates autophagy and can provide protection from a variety of cellular stressors.

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 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 Toward the assembly of heparin and heparan sulfate oligosaccharide libraries: efficient synthesis of uronic acid and disaccharide building blocks

Tetrahedron ◽  
2010 ◽  
Vol 66 (22) ◽  
pp. 3951-3962 ◽  
Author(s):  
Akihiro Saito ◽  
Masahiro Wakao ◽  
Hiroshi Deguchi ◽  
Aya Mawatari ◽  
Michael Sobel ◽  
...  
Keyword(s):  
Heparan Sulfate ◽  
Uronic Acid ◽  
Building Blocks ◽  
Efficient Synthesis

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.

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