It is part of a biopolymer in the bacterial cell wall, which is built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan (formerly called murein).
O-GlcNAcylation is the process of adding a single N-acetylglucosamine sugar to the serine or threonine of a protein.[4] Comparable to phosphorylation, addition or removal of N-acetylglucosamine is a means of activating or deactivating enzymes or transcription factors.[4] In fact, O-GlcNAcylation and phosphorylation often compete for the same serine/threonine sites.[4]O-GlcNAcylation most often occurs on chromatin proteins, and is often seen as a response to stress.[4]
Hyperglycemia increases O-GlcNAcylation, leading to insulin resistance.[5] Increased O-GlcNAcylation due to hyperglycemia is evidently a dysfunctional form of O-GlcNAcylation. O-GlcNAcylation decline in the brain with age is associated with cognitive decline. When O-GlcNAcylation was increased in the hippocampus of aged mice, spatial learning and memory improved.[6]
^Kamel M, Hanafi M, Bassiouni M (1991). "Inhibition of elastase enzyme release from human polymorphonuclear leukocytes by N-acetyl-galactosamine and N-acetyl-glucosamine". Clinical and Experimental Rheumatology. 9 (1): 17–21. PMID 2054963.
^Grigorian A, Araujo L, Naidu NN, Place DJ, Choudhury B, Demetriou M (November 2011). "N-acetylglucosamine inhibits T-helper 1 (Th1)/T-helper 17 (Th17) cell responses and treats experimental autoimmune encephalomyelitis". The Journal of Biological Chemistry. 286 (46): 40133–40141. doi:10.1074/jbc.M111.277814. PMC3220534. PMID 21965673.
^Sy M, Newton BL, Pawling J, Hayama KL, Cordon A, Yu Z, et al. (September 2023). "N-acetylglucosamine inhibits inflammation and neurodegeneration markers in multiple sclerosis: a mechanistic trial". Journal of Neuroinflammation. 20 (1): 209. doi:10.1186/s12974-023-02893-9. PMC10498575. PMID 37705084.
^ abcdHart GW, Slawson C, Ramirez-Correa G, Lagerlof O (2011). "Cross talk between O-GlcNAcylation and phosphorylation: roles in signaling, transcription, and chronic disease". Annual Review of Biochemistry. 80: 825–858. doi:10.1146/annurev-biochem-060608-102511. PMC3294376. PMID 21391816.
^Ma J, Hart GW (August 2013). "Protein O-GlcNAcylation in diabetes and diabetic complications". Expert Review of Proteomics. 10 (4): 365–380. doi:10.1586/14789450.2013.820536. PMC3985334. PMID 23992419.
^Wheatley EG, Albarran E, White CW, Bieri G, Sanchez-Diaz C, Pratt K, et al. (October 2019). "Neuronal O-GlcNAcylation Improves Cognitive Function in the Aged Mouse Brain". Current Biology. 29 (20): 3359–3369.e4. doi:10.1016/j.cub.2019.08.003. PMC7199460. PMID 31588002.
External linksedit
February 15, 2024
acetylglucosamine, glcnac, redirects, here, confused, with, glynac, glcnac, amide, derivative, monosaccharide, glucose, secondary, amide, between, glucosamine, acetic, acid, significant, several, biological, systems, haworth, projectionnamesiupac, name, acetyl. GlcNAc redirects here Not to be confused with GlyNAC N Acetylglucosamine GlcNAc is an amide derivative of the monosaccharide glucose It is a secondary amide between glucosamine and acetic acid It is significant in several biological systems N Acetylglucosamine Haworth projectionNamesIUPAC name b D Acetylamino 2 deoxy glucopyranoseOther names N Acetyl D glucosamineGlcNAcNAGIdentifiersCAS Number 7512 17 6 Y3D model JSmol Interactive imageBeilstein Reference 1247660ChEBI CHEBI 28009 NChEMBL ChEMBL447878 YChemSpider 22563 YECHA InfoCard 100 028 517EC Number 231 368 2Gmelin Reference 721281KEGG C03878PubChem CID 24139UNII V956696549 NCompTox Dashboard EPA DTXSID3045855InChI InChI 1S C8H15NO6 c1 3 11 9 5 7 13 6 12 4 2 10 15 8 5 14 h4 8 10 12 14H 2H2 1H3 H 9 11 t4 5 6 7 8 m1 s1 YKey OVRNDRQMDRJTHS FMDGEEDCSA N YInChI 1 C8H15NO6 c1 3 11 9 5 7 13 6 12 4 2 10 15 8 5 14 h4 8 10 12 14H 2H2 1H3 H 9 11 t4 5 6 7 8 m1 s1Key OVRNDRQMDRJTHS FMDGEEDCBLSMILES O C N C H 1 C H O C H O C H O C H 1O CO CPropertiesChemical formula C 8H 15N O 6Molar mass 221 21Melting point 211Related compoundsRelated Monosaccharides N AcetylgalactosamineRelated compounds GlucosamineGlucoseExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references N Acetylglucosamine moleculeIt is part of a biopolymer in the bacterial cell wall which is built from alternating units of GlcNAc and N acetylmuramic acid MurNAc cross linked with oligopeptides at the lactic acid residue of MurNAc This layered structure is called peptidoglycan formerly called murein GlcNAc is the monomeric unit of the polymer chitin which forms the exoskeletons of arthropods like insects and crustaceans It is the main component of the radulas of mollusks the beaks of cephalopods and a major component of the cell walls of most fungi Polymerized with glucuronic acid it forms hyaluronan GlcNAc has been reported to be an inhibitor of elastase release from human polymorphonuclear leukocytes range 8 17 inhibition however this is much weaker than the inhibition seen with N acetylgalactosamine range 92 100 1 Contents 1 Medical uses 2 O GlcNAcylation 3 See also 4 References 5 External linksMedical uses editIt has been proposed as a treatment for autoimmune diseases and recent tests have claimed some success 2 3 O GlcNAcylation editMain article O GlcNAc O GlcNAcylation is the process of adding a single N acetylglucosamine sugar to the serine or threonine of a protein 4 Comparable to phosphorylation addition or removal of N acetylglucosamine is a means of activating or deactivating enzymes or transcription factors 4 In fact O GlcNAcylation and phosphorylation often compete for the same serine threonine sites 4 O GlcNAcylation most often occurs on chromatin proteins and is often seen as a response to stress 4 Hyperglycemia increases O GlcNAcylation leading to insulin resistance 5 Increased O GlcNAcylation due to hyperglycemia is evidently a dysfunctional form of O GlcNAcylation O GlcNAcylation decline in the brain with age is associated with cognitive decline When O GlcNAcylation was increased in the hippocampus of aged mice spatial learning and memory improved 6 See also editKeratan sulfate N Acetylgalactosamine GalNAc N Acetyllactosamine synthase Wheat germ agglutinin a plant lectin that binds to this substrateReferences edit Kamel M Hanafi M Bassiouni M 1991 Inhibition of elastase enzyme release from human polymorphonuclear leukocytes by N acetyl galactosamine and N acetyl glucosamine Clinical and Experimental Rheumatology 9 1 17 21 PMID 2054963 Grigorian A Araujo L Naidu NN Place DJ Choudhury B Demetriou M November 2011 N acetylglucosamine inhibits T helper 1 Th1 T helper 17 Th17 cell responses and treats experimental autoimmune encephalomyelitis The Journal of Biological Chemistry 286 46 40133 40141 doi 10 1074 jbc M111 277814 PMC 3220534 PMID 21965673 Sy M Newton BL Pawling J Hayama KL Cordon A Yu Z et al September 2023 N acetylglucosamine inhibits inflammation and neurodegeneration markers in multiple sclerosis a mechanistic trial Journal of Neuroinflammation 20 1 209 doi 10 1186 s12974 023 02893 9 PMC 10498575 PMID 37705084 a b c d Hart GW Slawson C Ramirez Correa G Lagerlof O 2011 Cross talk between O GlcNAcylation and phosphorylation roles in signaling transcription and chronic disease Annual Review of Biochemistry 80 825 858 doi 10 1146 annurev biochem 060608 102511 PMC 3294376 PMID 21391816 Ma J Hart GW August 2013 Protein O GlcNAcylation in diabetes and diabetic complications Expert Review of Proteomics 10 4 365 380 doi 10 1586 14789450 2013 820536 PMC 3985334 PMID 23992419 Wheatley EG Albarran E White CW Bieri G Sanchez Diaz C Pratt K et al October 2019 Neuronal O GlcNAcylation Improves Cognitive Function in the Aged Mouse Brain Current Biology 29 20 3359 3369 e4 doi 10 1016 j cub 2019 08 003 PMC 7199460 PMID 31588002 External links editRe Multiple Sclerosis Retrieved from https en wikipedia org w index php title N Acetylglucosamine amp oldid 1179200076, wikipedia, wiki, book, books, library,
