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Hyaluronic acid information


Hyaluronic acid

Haworth projection
Names
IUPAC name
(1→4)-(2-Acetamido-2-deoxy-D-gluco)-(1→3)-D-glucuronoglycan
Systematic IUPAC name
Poly{[(2S,3R,4R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxane-2,4-diyl]oxy[(2R,3R,4R,5S,6S)-6-carboxy-3,4-dihydroxyoxane-2,5-diyl]oxy}
Identifiers
CAS Number
  • 9004-61-9 checkY
ChEBI
  • CHEBI:16336
ChemSpider
  • None
ECHA InfoCard 100.029.695 Edit this at Wikidata
EC Number
  • 232-678-0
PubChem CID
  • 3084050
UNII
  • S270N0TRQY checkY
CompTox Dashboard (EPA)
  • DTXSID90925319 DTXSID7046750, DTXSID90925319 Edit this at Wikidata
Properties
Chemical formula
(C14H21NO11)n
Pharmacology
ATC code
D03AX05 (WHO) M09AX01 (WHO), R01AX09 (WHO), S01KA01 (WHO)
Related compounds
Related compounds
  • D-Glucuronic acid and N-acetyl-D-glucosamine (monomers)
  • Sodium hyaluronate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Hyaluronic acid (/ˌh.əljʊəˈrɒnɪk/;[1][2] abbreviated HA; conjugate base hyaluronate), also called hyaluronan, is an anionic, nonsulfated glycosaminoglycan distributed widely throughout connective, epithelial, and neural tissues. It is unique among glycosaminoglycans as it is non-sulfated, forms in the plasma membrane instead of the Golgi apparatus, and can be very large: human synovial HA averages about 7 million Da per molecule, or about 20,000 disaccharide monomers,[3] while other sources mention 3–4 million Da.[4]

The average 70 kg (150 lb) person has roughly 15 grams of hyaluronan in the body, one third of which is turned over (i.e., degraded and synthesized) per day.[5]

As one of the chief components of the extracellular matrix, it contributes significantly to cell proliferation and migration, and is involved in the progression of many malignant tumors.[6][7] Hyaluronic acid is also a component of the group A streptococcal extracellular capsule,[8] and is believed to play a role in virulence.[9][10][11]

  1. ^ "Hyaluronic Acid | Definition of Hyaluronic Acid by Oxford Dictionary". Lexico Dictionaries | English. Archived from the original on October 6, 2019.
  2. ^ "Hyaluronic acid". wordreference.com.
  3. ^ Fraser JR, Laurent TC, Laurent UB (1997). "Hyaluronan: its nature, distribution, functions and turnover". J. Intern. Med. 242 (1): 27–33. doi:10.1046/j.1365-2796.1997.00170.x. PMID 9260563. S2CID 37551992.
  4. ^ Cite error: The named reference pmid8406685 was invoked but never defined (see the help page).
  5. ^ Stern R (2004). "Hyaluronan catabolism: a new metabolic pathway". Eur. J. Cell Biol. 83 (7): 317–25. doi:10.1078/0171-9335-00392. PMID 15503855.
  6. ^ Stern, Robert, ed. (2009). Hyaluronan in cancer biology (1st ed.). San Diego, CA: Academic Press/Elsevier. ISBN 978-0-12-374178-3.
  7. ^ Itano, Naoki (2002). "Abnormal accumulation of hyaluronan matrix diminishes contact inhibition of cell growth and promotes cell migration". Proceedings of the National Academy of Sciences. 99 (6). Proc Natl Acad Sci USA: 3609–3614. Bibcode:2002PNAS...99.3609I. doi:10.1073/pnas.052026799. PMC 122571. PMID 11891291.
  8. ^ Sugahara K, Schwartz NB, Dorfman A (1979). "Biosynthesis of hyaluronic acid by Streptococcus" (PDF). J. Biol. Chem. 254 (14): 6252–6261. doi:10.1016/S0021-9258(18)50356-2. PMID 376529.
  9. ^ Rao S, Pham TH, Poudyal S, Cheng LW, Nazareth SC, Wang PC, et al. (2021-04-27). "First report on genetic characterization, cell-surface properties and pathogenicity of Lactococcus garvieae, emerging pathogen isolated from cage-cultured cobia (Rachycentron canadum)". Transboundary and Emerging Diseases. 69 (3). Hindawi Limited: 1197–1211. doi:10.1111/tbed.14083. ISSN 1865-1674. PMID 33759359. S2CID 232338928.
  10. ^ Wessels MR, Moses AE, Goldberg JB, DiCesare TJ (1991). "Hyaluronic acid capsule is a virulence factor for mucoid group A streptococci". Proc. Natl. Acad. Sci. U.S.A. 88 (19): 8317–8321. Bibcode:1991PNAS...88.8317W. doi:10.1073/pnas.88.19.8317. PMC 52499. PMID 1656437.
  11. ^ Schrager HM, Rheinwald JG, Wessels MR (1996). "Hyaluronic acid capsule and the role of streptococcal entry into keratinocytes in invasive skin infection". J. Clin. Invest. 98 (9): 1954–1958. doi:10.1172/JCI118998. PMC 507637. PMID 8903312.

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N-linked glycosylation or O-linked glycosylation of the proteoglycan Hyaluronic acid (also known as hyaluronan), which is synthesized by integral membrane...

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Hyaluronidases are a family of enzymes that catalyse the degradation of hyaluronic acid. Karl Meyer classified these enzymes in 1971, into three distinct groups...

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for the injection of cosmetic wrinkle fillers like hyaluronic acid, collagen, poly-L-lactic acid, CaHA, etc., or for fat transfer (Liposuction). The...

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both endogenous and synthetic chemicals. Endogenous molecules include hyaluronic acid, glucosamine, and chondroitin sulfate. Felson, David T.; Kim, Young-Jo...

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anti-inflammatory agents, the most common of which are corticosteroids. Hyaluronic acid, because of its high viscosity, is sometimes used to replace bursa...

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