Synthetic approach towards sulfated chondroitin di-, tri- and tetrasaccharides corresponding to the repeating unit

Carbohydrate Research
J TamuraT Ogawa

Abstract

Chondroitin di-, tri- and tetrasaccharides, as well as their 4-, 6-mono- and 4,6-disulfates as their 4-methoxyphenyl glycosides, were systematically synthesized. Target disaccharides having beta GalNAc-(1-->4)-beta GlcA sequences were obtained starting from the corresponding pivotal chondroitin disaccharide precursor. A trisaccharide intermediate, which was synthesized by coupling of glucuronate imidate with a known disaccharide acceptor, was transformed into the sulfated and non-sulfated chondroitin trisaccharides. Chondroitin tetrasaccharide and the corresponding 4-disulfate, 6-disulfate as well as 4,6-tetrasulfate were also obtained based on the strategy developed above starting from the reported tetrasaccharide having [beta GalN3-(1-->4)-beta GlcA2] sequence.

Citations

May 21, 1999·Carbohydrate Research·J C JacquinetJ P Combal
Mar 22, 2006·Chemical Communications : Chem Comm·Hirotaka UzawaYoshihiro Nishida
Mar 7, 2007·Organic & Biomolecular Chemistry·Hai Yu, Xi Chen
Dec 3, 2010·The Journal of Biological Chemistry·Satomi NadanakaHiroshi Kitagawa
Mar 15, 2015·Bioorganic & Medicinal Chemistry Letters·Masahiro WakaoYasuo Suda
May 8, 2019·Nature Chemical Biology·Kazuma SakamotoKenji Kadomatsu
Jul 16, 2019·Future Medicinal Chemistry·Shuang YangYinghong Wang
Nov 17, 2012·Chemistry : a European Journal·Guillaume DesprasJean-Maurice Mallet
Mar 5, 2021·Experimental Neurology·Sadayuki ItoKazuma Sakamoto
Jun 24, 2004·Journal of the American Chemical Society·Sarah E TullyLinda C Hsieh-Wilson
Jul 12, 2002·Carbohydrate Research·Derek K WattGeorge C Slim
May 15, 2018·The Journal of Organic Chemistry·Shuang YangPingsheng Lei

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.