Chemical synthesis of α(2,8) octasialosides, the minimum structure of polysialic acids

2020 ◽  
Vol 56 (85) ◽  
pp. 12981-12984
Author(s):  
Ryousuke Koinuma ◽  
Kazuki Tohda ◽  
Taku Aoyagi ◽  
Hiroshi Tanaka
Keyword(s):  
Sialic Acid ◽  
Chemical Synthesis ◽  
Protecting Groups ◽  
Polysialic Acids

Modification of a sialic acid with just carbonyl protecting groups opened the door to a chemical synthesis of polysialic acids.

scholarly journals Postsynthetic On-Column 2′ Functionalization of RNA by Convenient Versatile Method

2020 ◽  
Vol 21 (14) ◽  
pp. 5127
Author(s):  
Olga A. Krasheninina ◽  
Veniamin S. Fishman ◽  
Alexander A. Lomzov ◽  
Alexey V. Ustinov ◽  
Alya G. Venyaminova
Keyword(s):  
Chemical Synthesis ◽  
Physicochemical Properties ◽  
Functional Groups ◽  
Convenient Method ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Protecting Groups ◽  
Hydroxyl Group ◽  
Phase Synthesis ◽  
Wide Range

We report a universal straightforward strategy for the chemical synthesis of modified oligoribonucleotides containing functional groups of different structures at the 2′ position of ribose. The on-column synthetic concept is based on the incorporation of two types of commercial nucleotide phosphoramidites containing orthogonal 2′-O-protecting groups, namely 2′-O-thiomorpholine-carbothioate (TC, as “permanent”) and 2′-O-tert-butyl(dimethyl)silyl (tBDMS, as “temporary”), to RNA during solid-phase synthesis. Subsequently, the support-bound RNA undergoes selective deprotection and follows postsynthetic 2′ functionalization of the naked hydroxyl group. This convenient method to tailor RNA, utilizing the advantages of solid phase approaches, gives an opportunity to introduce site-specifically a wide range of linkers and functional groups. By this strategy, a series of RNAs containing diverse 2′ functionalities were synthesized and studied with respect to their physicochemical properties.

ChemInform Abstract: The Chemical Synthesis of Glycosylphosphatidylinositol Anchors from Trypanosoma Cruzi Trypomastigote Mucins - Exploration of Ester- and Acetal-Type Permanent Protecting Groups

ChemInform ◽  
2008 ◽  
Vol 39 (26) ◽  
Author(s):  
Dmitry V. Yashunsky ◽  
Vladimir S. Borodkin ◽  
Philip G. McGivern ◽  
Michael A. J. Ferguson ◽  
Andrei V. Nikolaev
Keyword(s):  
Trypanosoma Cruzi ◽  
Chemical Synthesis ◽  
Protecting Groups

Chemical Synthesis of a Synthetic Analogue of the Sialic Acid-Binding Lectin Siglec-7

ChemBioChem ◽  
2014 ◽  
Vol 15 (17) ◽  
pp. 2503-2507 ◽  
Author(s):  
Masayuki Izumi ◽  
Akihisa Otsuki ◽  
Mika Nishihara ◽  
Ryo Okamoto ◽  
Yasuhiro Kajihara
Keyword(s):  
Sialic Acid ◽  
Chemical Synthesis ◽  
Synthetic Analogue ◽  
Sialic Acid Binding ◽  
Binding Lectin

Chemical Synthesis and Enzymatic Testing of CMP-Sialic Acid Derivatives

ChemBioChem ◽  
2012 ◽  
Vol 13 (17) ◽  
pp. 2605-2615 ◽  
Author(s):  
Saskia Wolf ◽  
Svenja Warnecke ◽  
Jörg Ehrit ◽  
Friedrich Freiberger ◽  
Rita Gerardy-Schahn ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Chemical Synthesis

scholarly journals Tissue-based metabolic labeling of polysialic acids in living primary hippocampal neurons

2015 ◽  
Vol 112 (3) ◽  
pp. E241-E248 ◽  
Author(s):  
Kyungtae Kang ◽  
Sunghoon Joo ◽  
Ji Yu Choi ◽  
Sujeong Geum ◽  
Seok-Pyo Hong ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Hippocampal Neurons ◽  
Neuronal Development ◽  
Polysialic Acid ◽  
Metabolic Labeling ◽  
Primary Hippocampal Neurons ◽  
Polysialic Acids ◽  
Conventional Cell ◽  
Vitro Analysis

The posttranslational modification of neural cell-adhesion molecule (NCAM) with polysialic acid (PSA) and the spatiotemporal distribution of PSA-NCAM play an important role in the neuronal development. In this work, we developed a tissue-based strategy for metabolically incorporating an unnatural monosaccharide, peracetylated N-azidoacetyl-d-mannosamine, in the sialic acid biochemical pathway to present N-azidoacetyl sialic acid to PSA-NCAM. Although significant neurotoxicity was observed in the conventional metabolic labeling that used the dissociated neuron cells, neurotoxicity disappeared in this modified strategy, allowing for investigation of the temporal and spatial distributions of PSA in the primary hippocampal neurons. PSA-NCAM was synthesized and recycled continuously during neuronal development, and the two-color labeling showed that newly synthesized PSA-NCAMs were transported and inserted mainly to the growing neurites and not significantly to the cell body. This report suggests a reliable and cytocompatible method for in vitro analysis of glycans complementary to the conventional cell-based metabolic labeling for chemical glycobiology.

scholarly journals Sialometabolism in Brain Health and Alzheimer’s Disease

2021 ◽  
Vol 15 ◽  
Author(s):  
Punam Rawal ◽  
Liqin Zhao
Keyword(s):  
Alzheimer’S Disease ◽  
Alzheimer's Disease ◽  
Sialic Acid ◽  
Late Onset ◽  
Critical Role ◽  
Sialic Acids ◽  
Polysialic Acids ◽  
Neuronal Connections ◽  
Acidic Sugars ◽  
Neuronal Sprouting

Sialic acids refer to a unique family of acidic sugars with a 9-carbon backbone that are mostly found as terminal residues in glycan structures of glycoconjugates including both glycoproteins and glycolipids. The highest levels of sialic acids are expressed in the brain where they regulate neuronal sprouting and plasticity, axon myelination and myelin stability, as well as remodeling of mature neuronal connections. Moreover, sialic acids are the sole ligands for microglial Siglecs (sialic acid-binding immunoglobulin-type lectins), and sialic acid-Siglec interactions have been indicated to play a critical role in the regulation of microglial homeostasis in a healthy brain. The recent discovery of CD33, a microglial Siglec, as a novel genetic risk factor for late-onset Alzheimer’s disease (AD), highlights the potential role of sialic acids in the development of microglial dysfunction and neuroinflammation in AD. Apart from microglia, sialic acids have been found to be involved in several other major changes associated with AD. Elevated levels of serum sialic acids have been reported in AD patients. Alterations in ganglioside (major sialic acid carrier) metabolism have been demonstrated as an aggravating factor in the formation of amyloid pathology in AD. Polysialic acids are linear homopolymers of sialic acids and have been implicated to be an important regulator of neurogenesis that contributes to neuronal repair and recovery from neurodegeneration such as in AD. In summary, this article reviews current understanding of neural functions of sialic acids and alterations of sialometabolism in aging and AD brains. Furthermore, we discuss the possibility of looking at sialic acids as a promising novel therapeutic target for AD intervention.

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