Biological functions of iduronic acid in chondroitin/dermatan sulfate.
paper
Cited
Public
- Authors
- Thelin, Martin A; Bartolini, Barbara; Axelsson, Jakob; Gustafsson, Renata; Tykesson, Emil; Pera, Edgar; Oldberg, Γ ke; Maccarana, Marco; Malmstrom, Anders
- Year
- 2013
- Journal
- The FEBS journal
- PMID
- 23441919
- DOI
- 10.1111/febs.12214
- PMCID
- PMC3717172
The presence of iduronic acid in chondroitin/dermatan sulfate changes the properties of the polysaccharides because it generates a more flexible chain with increased binding potentials. Iduronic acid in chondroitin/dermatan sulfate influences multiple cellular properties, such as migration, proliferation, differentiation, angiogenesis and the regulation of cytokine/growth factor activities. Under pathological conditions such as wound healing, inflammation and cancer, iduronic acid has diverse regulatory functions. Iduronic acid is formed by two epimerases (i.e. dermatan sulfate epimerase 1 and 2) that have different tissue distribution and properties. The role of iduronic acid in chondroitin/dermatan sulfate is highlighted by the vast changes in connective tissue features in patients with a new type of Ehler-Danlos syndrome: adducted thumb-clubfoot syndrome. Future research aims to understand the roles of the two epimerases and their interplay with the sulfotransferases involved in chondroitin sulfate/dermatan sulfate biosynthesis. Furthermore, a better definition of chondroitin/dermatan sulfate functions using different knockout models is needed. In this review, we focus on the two enzymes responsible for iduronic acid formation, as well as the role of iduronic acid in health and disease.
Structure of CS/DS and conformations of IdoA. (A) The domains of variable length containing blocks of IdoA, alternating IdoA and GlcA or blocks of GlcA. (B) The epimerase reaction. (C) Conformations of IdoA.
(A) DS-epi1 and DS-epi2 domain structures. (B) Three-dimensional modelling of the DS-epi1 epimerase domain based on the crystal structure of heparinase II. A chondroitin sulfate tetrasaccharide is positioned in the groove containing the active site.
Formation of IdoA in CS/DS. The amount and distribution of IdoA depends upon the expression level of the DS epimerases and D4ST1.
Overview of the functions of IdoA in CS/DS. Role of IdoA in the storage of cytokines growth factors and collagen fibril formation (A), Borrelia infection (B), atherosclerosis (C), coagulation (D), P-selectin-dependent leukocyte recruitment (E), activation of cytokine and growth factor receptors (F) and leukocyte recruitment by ICAM (G).
β Prev
21β38 of 38
No entities extracted from this document yet.
No uploaded files.
Not in any collection.
In this knowledge base
| Title | Year | PMID |
|---|---|---|
| A genome wide association study of fast beta EEG in families of European ancestry. | 2017 | 28040410 |
External
| Title | Authors | Journal | Year | Link |
|---|---|---|---|---|
| Change in the chondroitin/dermatan structure in distal lung tissue from COPD patients. | Alsafadi HN et al. | β | 2026 | β |
| Leveraging mirror-image glycans in carbohydrate materials. | Weh D et al. | β | 2026 | β |
| Only in Halobacterium salinarum: Sugar modifications unique to an archaeal N-linked glycan. | Eichler J et al. | β | 2026 | β |
| Acidogenic fermentation of Ulva in a fed-batch reactor system: tubular versus foliose biomass. | Lawrence J et al. | β | 2025 | β |
| Dermatan Sulfate: Structure, Biosynthesis, and Biological Roles. | Chen C et al. | β | 2025 | β |
| Group A Streptococcus interacts with glycosaminoglycans via M proteins to modulate bacterial adherence in vitro. | McEwan TB et al. | β | 2025 | β |
| Identification of lens-regulated genes driving anterior eye development. | Murcia-Belmonte V et al. | β | 2025 | β |
| Identification of the D-glucuronyl C5-epimerase that introduces iduronic acid into N-linked glycans decorating archaeal glycoproteins. | Vershinin Z et al. | β | 2025 | β |
| Segmented ring-mesh model of glycosaminoglycan chains based on the 3D analysis of normal individual and musculocontractural Ehlers-Danlos syndrome skin using scanning transmission electron microscopy. | Takahashi N et al. | β | 2025 | β |
| Structural Variants of Dermatan Sulfate Can Affect the Expression of Proteins Involved in Breast Cancer Cell Survival. | Wisowski G et al. | β | 2025 | β |
| A biological guide to glycosaminoglycans: current perspectives and pending questions. | Ricard-Blum S et al. | β | 2024 | β |
| Dermatan Sulfate Affects the Activation of the Necroptotic Effector MLKL in Breast Cancer Cell Lines via the NFΞΊB Pathway and Rac-Mediated Oxidative Stress. | Wisowski G et al. | β | 2024 | β |
| Genome-wide DNA methylation and gene expression in human placentas derived from assisted reproductive technology. | Auvinen P et al. | β | 2024 | β |
| Biochemical and crystallographic assessments of the effect of 4,6-O-disulfated disaccharide moieties in chondroitin sulfate E on chondroitinase ABC I activity. | Watanabe I et al. | β | 2023 | β |
| Biomaterials and tissue engineering approaches using glycosaminoglycans for tissue repair: Lessons learned from the native extracellular matrix. | Menezes R et al. | β | 2023 | β |
| Chemistry and Function of Glycosaminoglycans in the Nervous System. | Schwartz NB et al. | β | 2023 | β |
| Collagen Network Formation in In Vitro Models of Musculocontractural Ehlers-Danlos Syndrome. | Hashimoto A et al. | β | 2023 | β |
| Genome-wide DNA methylation, imprinting, and gene expression in human placentas derived from Assisted Reproductive Technology | Auvinen P et al. | β | 2023 | β |
| Histories of Dermatan Sulfate Epimerase and Dermatan 4-<i>O</i>-Sulfotransferase from Discovery of Their Enzymes and Genes to Musculocontractural Ehlers-Danlos Syndrome. | Mizumoto S et al. | β | 2023 | β |
| Mouse Models of Musculocontractural Ehlers-Danlos Syndrome. | Yoshizawa T et al. | β | 2023 | β |
| Precolumn derivatization LC-MS/MS method to simultaneous quantitation of 10 monosaccharides in rat plasma. | Li M et al. | β | 2023 | β |
| The effect of the sulfation patterns of dermatan and chondroitin sulfate from vertebrates and ascidians on their neuritogenic and neuroprotective properties. | Medeiros TB et al. | β | 2023 | β |
| C7 Epimerization of Benzylidene-Protected Ξ²-d-Idopyranosides Brings Structural Insights into Idose Conformational Flexibility. | Cloutier M et al. | β | 2022 | β |
| Cell Surface Glycosaminoglycans as Receptors for Adhesion of <i>Candida</i> spp. to Corneal Cells. | Ordiales H et al. | β | 2022 | β |
| Dermatan Sulfate Affects Breast Cancer Cell Function via the Induction of Necroptosis. | Wisowski G et al. | β | 2022 | β |
| Pathogenesis of COVID-19 described through the lens of an undersulfated and degraded epithelial and endothelial glycocalyx. | du Preez HN et al. | β | 2022 | β |
| The Specific Role of Dermatan Sulfate as an Instructive Glycosaminoglycan in Tissue Development. | Mizumoto S et al. | β | 2022 | β |
| An Overview of <i>in vivo</i> Functions of Chondroitin Sulfate and Dermatan Sulfate Revealed by Their Deficient Mice. | Mizumoto S et al. | β | 2021 | β |
| Congenital Disorders of Deficiency in Glycosaminoglycan Biosynthesis. | Mizumoto S et al. | β | 2021 | β |
| Discrimination of sulfated isomers of chondroitin sulfate disaccharides by HILIC-MS. | Poyer S et al. | β | 2021 | β |
| Modeling Extracellular Matrix-Cell Interactions in Lung Repair and Chronic Disease. | Hackett TL et al. | β | 2021 | β |
| Neural Tissue Homeostasis and Repair Is Regulated via CS and DS Proteoglycan Motifs. | Hayes AJ et al. | β | 2021 | β |
| New Insights Into Human Hyaluronidase 4/Chondroitin Sulphate Hydrolase. | Maciej-Hulme ML | β | 2021 | β |
| Novel Insight Into Glycosaminoglycan Biosynthesis Based on Gene Expression Profiles. | Huang YF et al. | β | 2021 | β |
| Structural analysis of glycosaminoglycans from Oviductus ranae. | Huang H et al. | β | 2021 | β |
| The CNS/PNS Extracellular Matrix Provides Instructive Guidance Cues to Neural Cells and Neuroregulatory Proteins in Neural Development and Repair. | Melrose J et al. | β | 2021 | β |
| The structure of human dermatan sulfate epimerase 1 emphasizes the importance of C5-epimerization of glucuronic acid in higher organisms. | Hasan M et al. | β | 2021 | β |
| Evidence of biglycan structure-function in bone homeostasis and aging. | Miguez PA | β | 2020 | β |
| Increased Microvessel and Arteriole Density in the Contracted Side of the Relapsed Clubfoot. | Novotny T et al. | β | 2020 | β |
| Mining GWAS and eQTL data for CF lung disease modifiers by gene expression imputation. | Dang H et al. | β | 2020 | β |
| Structural analysis of glycosaminoglycans from Colla corii asini by liquid chromatography-electrospray ion trap mass spectrometry. | Huang H et al. | β | 2020 | β |
| Chondroitin sulfate inhibits secretion of TNF and CXCL8 from human mast cells stimulated by IL-33. | Gross AR et al. | β | 2019 | β |
| Glycosaminoglycans: A Link Between Development and Regeneration in the Lung. | WigΓ©n J et al. | β | 2019 | β |
| Iduronate-2-Sulfatase-Regulated Dermatan Sulfate Levels Potentiate the Invasion of Breast Cancer Epithelia through Collagen Matrix. | Singh V et al. | β | 2019 | β |
| Porcine Circovirus 2 Uses a Multitude of Weak Binding Sites To Interact with Heparan Sulfate, and the Interactions Do Not Follow the Symmetry of the Capsid. | Dhindwal S et al. | β | 2019 | β |
| Structural alteration of glycosaminoglycan side chains and spatial disorganization of collagen networks in the skin of patients with mcEDS-CHST14. | Hirose T et al. | β | 2019 | β |
| Substrate binding mode and catalytic mechanism of human heparan sulfate d-glucuronyl C5 epimerase. | Debarnot C et al. | β | 2019 | β |
| Synthesis of Heparan Sulfate- and Dermatan Sulfate-Related Oligosaccharides via Iterative Chemoselective Glycosylation Exploiting Conformationally Disarmed [2.2.2] l-Iduronic Lactone Thioglycosides. | Jeanneret RA et al. | β | 2019 | β |
| The dual role of the glycosaminoglycan chondroitin-6-sulfate in the development, progression and metastasis of cancer. | PudeΕko A et al. | β | 2019 | β |
| Viscera of fishes as raw material for extraction of glycosaminoglycans of pharmacological interest. | Nogueira AV et al. | β | 2019 | β |
| Aerogels made of chitosan and chondroitin sulfate at high degree of neutralization: Biological properties toward wound healing. | Concha M et al. | β | 2018 | β |
| Biodiversity of CS-proteoglycan sulphation motifs: chemical messenger recognition modules with roles in information transfer, control of cellular behaviour and tissue morphogenesis. | Hayes A et al. | β | 2018 | β |
| Dendritic Cell Migration to Skin-Draining Lymph Nodes Is Controlled by Dermatan Sulfate and Determines Adaptive Immunity Magnitude. | Nadafi R et al. | β | 2018 | β |
| Dermatan sulfate epimerase 1 and dermatan 4-<i>O</i>-sulfotransferase 1 form complexes that generate long epimerized 4-<i>O</i>-sulfated blocks. | Tykesson E et al. | β | 2018 | β |
| Extracellular matrix and traumatic brain injury. | George N et al. | β | 2018 | β |
| Gene expression of the two developmentally regulated dermatan sulfate epimerases in the Xenopus embryo. | Gouignard N et al. | β | 2018 | β |
| Glycosaminoglycans from a Sea Snake (<i>Lapemis curtus</i>): Extraction, Structural Characterization and Antioxidant Activity. | Bai M et al. | β | 2018 | β |
| Glycosaminoglycans from grey triggerfish and smooth hound skins: Rheological, Anti-inflammatory and wound healing properties. | Krichen F et al. | β | 2018 | β |
| Identification of novel binding sites for heparin in receptor protein-tyrosine phosphatase (RPTPΟ): Implications for proteoglycan signaling. | Katagiri Y et al. | β | 2018 | β |
| Medical application of glycosaminoglycans: a review. | KΓΆwitsch A et al. | β | 2018 | β |
| Quantifying extracellular matrix turnover in human lung scaffold cultures. | Rosmark O et al. | β | 2018 | β |
| The metalloproteinase-proteoglycans ADAMTS7 and ADAMTS12 provide an innate, tendon-specific protective mechanism against heterotopic ossification. | Mead TJ et al. | β | 2018 | β |
| A genome wide association study of fast beta EEG in families of European ancestry. | Meyers JL et al. | β | 2017 | β |
| Defect in dermatan sulfate in urine of patients with Ehlers-Danlos syndrome caused by a CHST14/D4ST1 deficiency. | Mizumoto S et al. | β | 2017 | β |
| Glycosaminoglycanomics: where we are. | Ricard-Blum S et al. | β | 2017 | β |
| Glycosaminoglycans are involved in bacterial adherence to lung cells. | Rajas O et al. | β | 2017 | β |
| Increased deposition of glycosaminoglycans and altered structure of heparan sulfate in idiopathic pulmonary fibrosis. | Westergren-Thorsson G et al. | β | 2017 | β |
| Isomer separation and effect of the degree of polymerization on the gas-phase structure of chondroitin sulfate oligosaccharides analyzed by ion mobility and tandem mass spectrometry. | Poyer S et al. | β | 2017 | β |
| Sulfation of Glycosaminoglycans and Its Implications in Human Health and Disorders. | Soares da Costa D et al. | β | 2017 | β |
| Biosynthesis of glycosaminoglycans: associated disorders and biochemical tests. | Sasarman F et al. | β | 2016 | β |
| Chemical Synthesis of Glycosaminoglycans. | Mende M et al. | β | 2016 | β |
| Deciphering the Mode of Action of the Processive Polysaccharide Modifying Enzyme Dermatan Sulfate Epimerase 1 by Hydrogen-Deuterium Exchange Mass Spectrometry. | Tykesson E et al. | β | 2016 | β |
| Different Use of Cell Surface Glycosaminoglycans As Adherence Receptors to Corneal Cells by Gram Positive and Gram Negative Pathogens. | GarcΓa B et al. | β | 2016 | β |
| Germline ablation of dermatan-4O-sulfotransferase1 reduces regeneration after mouse spinal cord injury. | Rost S et al. | β | 2016 | β |
| Musculocontractural Ehlers-Danlos syndrome and neurocristopathies: dermatan sulfate is required for Xenopus neural crest cells to migrate and adhere to fibronectin. | Gouignard N et al. | β | 2016 | β |
| The stereoselectivities of tributyltin hydride-mediated reductions of 5-bromo-D-glucuronides to L-iduronides are dependent on the anomeric substituent: syntheses and DFT calculations. | Mohamed S et al. | β | 2016 | β |
| Chondroitin / dermatan sulfate modification enzymes in zebrafish development. | Habicher J et al. | β | 2015 | β |
| Dermatan Sulfate-Free Mice Display Embryological Defects and Are Neonatal Lethal Despite Normal Lymphoid and Non-Lymphoid Organogenesis. | Stachtea XN et al. | β | 2015 | β |
| Genetic heterogeneity and clinical variability in musculocontractural Ehlers-Danlos syndrome caused by impaired dermatan sulfate biosynthesis. | Syx D et al. | β | 2015 | β |
| Heparin and related polysaccharides: synthesis using recombinant enzymes and metabolic engineering. | Suflita M et al. | β | 2015 | β |
| Identification of chondroitin sulfate linkage region glycopeptides reveals prohormones as a novel class of proteoglycans. | Noborn F et al. | β | 2015 | β |
| Interleukin-34 promotes tumor progression and metastatic process in osteosarcoma through induction of angiogenesis and macrophage recruitment. | SΓ©galiny AI et al. | β | 2015 | β |
| Molecular interactions between chondroitin-dermatan sulfate and growth factors/receptors/matrix proteins. | Mizumoto S et al. | β | 2015 | β |
| Mutations in Biosynthetic Enzymes for the Protein Linker Region of Chondroitin/Dermatan/Heparan Sulfate Cause Skeletal and Skin Dysplasias. | Mizumoto S et al. | β | 2015 | β |
| Partial filling affinity capillary electrophoresis including adsorption energy distribution calculations--towards reliable and feasible biomolecular interaction studies. | Witos J et al. | β | 2015 | β |
| Role for chondroitin sulfate glycosaminoglycan in NEDD9-mediated breast cancer cell growth. | Iida J et al. | β | 2015 | β |
| Active signals, gradient formation and regional specificity in neural induction. | Pera EM et al. | β | 2014 | β |
| Dermatan sulfate epimerase 1 deficient mice as a model for human abdominal wall defects. | Gustafsson R et al. | β | 2014 | β |
| Influence of proteolytic-antiproteolytic enzymes and prooxidative-antioxidative factors on proteoglycan alterations in children with juvenile idiopathic arthritis. | Winsz-Szczotka K et al. | β | 2014 | β |
| Masquerading microbial pathogens: capsular polysaccharides mimic host-tissue molecules. | Cress BF et al. | β | 2014 | β |
| Partial-filling affinity capillary electrophoresis and quartz crystal microbalance with adsorption energy distribution calculations in the study of biomolecular interactions with apolipoprotein E as interaction partner. | Lipponen K et al. | β | 2014 | β |
| Synthesis and characterization of proteoglycan-mimetic graft copolymers with tunable glycosaminoglycan density. | Place LW et al. | β | 2014 | β |
| Urinary glycosaminoglycan (uGAG) excretion in healthy pediatric and adolescent population. | Komosinska-Vassev K et al. | β | 2014 | β |