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Glycation

February 16, 2024

Not to be confused with Glycosylation.

Glycation (non-enzymatic glycosylation) is the covalent attachment of a sugar to a protein, lipid or nucleic acid molecule.[1] Typical sugars that participate in glycation are glucose, fructose, and their derivatives. Glycation is the non-enzymatic process responsible for many (e.g. micro and macrovascular) complications in diabetes mellitus and is implicated in some diseases and in aging.[2][3][4] Glycation end products are believed to play a causative role in the vascular complications of diabetes mellitus.[5]

In contrast with glycation, glycosylation is the enzyme-mediated ATP-dependent attachment of sugars to protein or lipid.[1] Glycosylation occurs at defined sites on the target molecule. It is a common form of post-translational modification of proteins and is required for the functioning of the mature protein.

Biochemistry edit

 
Glycation pathway via Amadori rearrangement (in HbA1c, R is typically N-terminal valine)[6]
 
Imidazolones (R = CH2CH(OH)CH(OH)CH2OH) are typical glycation products. They arise by the condensation of 3-deoxyglucosone with the guanidine group of an arginine residue.[7]

Glycations occur mainly in the bloodstream to a small proportion of the absorbed simple sugars: glucose, fructose, and galactose. It appears that fructose has approximately ten times the glycation activity of glucose, the primary body fuel.[8] Glycation can occur through Amadori reactions, Schiff base reactions, and Maillard reactions; which lead to advanced glycation end products (AGEs).[1]

Biomedical implications edit

Red blood cells have a consistent lifespan of 120 days and are accessible for measurement of glycated hemoglobin. Measurement of HbA1c—the predominant form of glycated hemoglobin—enables medium-term blood sugar control to be monitored in diabetes.

Some glycation products are implicated in many age-related chronic diseases, including cardiovascular diseases (the endothelium, fibrinogen, and collagen are damaged) and Alzheimer's disease (amyloid proteins are side-products of the reactions progressing to AGEs).[9][10]

Long-lived cells (such as nerves and different types of brain cell), long-lasting proteins (such as crystallins of the lens and cornea), and DNA can sustain substantial glycation over time. Damage by glycation results in stiffening of the collagen in the blood vessel walls, leading to high blood pressure, especially in diabetes.[11] Glycations also cause weakening of the collagen in the blood vessel walls,[12] which may lead to micro- or macro-aneurysm; this may cause strokes if in the brain.

DNA glycation edit

The term DNA glycation applies to DNA damage induced by reactive carbonyls (principally methylglyoxal and glyoxal) that are present in cells as by-products of sugar metabolism.[13] Glycation of DNA can cause mutation, breaks in DNA and cytotoxicity.[13] Guanine in DNA is the base most susceptible to glycation. Glycated DNA, as a form of damage, appears to be as frequent as the more well studied oxidative DNA damage. A protein, designated DJ-1 (also known as PARK7), is employed in the repair of glycated DNA bases in humans, and homologs of this protein have also been identified in bacteria.[13]

See also edit

Additional reading edit

  • Ahmed N, Furth AJ (July 1992). "Failure of common glycation assays to detect glycation by fructose". Clin. Chem. 38 (7): 1301–3. doi:10.1093/clinchem/38.7.1301. PMID 1623595.
  • Vlassara H (June 2005). "Advanced glycation in health and disease: role of the modern environment". Annals of the New York Academy of Sciences. 1043 (1): 452–60. Bibcode:2005NYASA1043..452V. doi:10.1196/annals.1333.051. PMID 16037266. S2CID 20952378.

References edit

  1. ^ a b c Lima, M.; Baynes, J. W. (2013-01-01), "Glycation", in Lennarz, William J.; Lane, M. Daniel (eds.), Encyclopedia of Biological Chemistry (Second Edition), Waltham: Academic Press, pp. 405–411, doi:10.1016/b978-0-12-378630-2.00120-1, ISBN 978-0-12-378631-9, retrieved 2020-12-16
  2. ^ Glenn, J.; Stitt, A. (2009). "The role of advanced glycation end products in retinal ageing and disease". Biochimica et Biophysica Acta (BBA) - General Subjects. 1790 (10): 1109–1116. doi:10.1016/j.bbagen.2009.04.016. PMID 19409449.
  3. ^ Semba, R. D.; Ferrucci, L.; Sun, K.; Beck, J.; Dalal, M.; Varadhan, R.; Walston, J.; Guralnik, J. M.; Fried, L. P. (2009). "Advanced glycation end products and their circulating receptors predict cardiovascular disease mortality in older community-dwelling women". Aging Clinical and Experimental Research. 21 (2): 182–190. doi:10.1007/BF03325227. PMC 2684987. PMID 19448391.
  4. ^ Semba, R.; Najjar, S.; Sun, K.; Lakatta, E.; Ferrucci, L. (2009). "Serum carboxymethyl-lysine, an advanced glycation end product, is associated with increased aortic pulse wave velocity in adults". American Journal of Hypertension. 22 (1): 74–79. doi:10.1038/ajh.2008.320. PMC 2637811. PMID 19023277.
  5. ^ Yan, S. F.; D'Agati, V.; Schmidt, A. M.; Ramasamy, R. (2007). "Receptor for Advanced Glycation Endproducts (RAGE): a formidable force in the pathogenesis of the cardiovascular complications of diabetes & aging". Current Molecular Medicine. 7 (8): 699–710. doi:10.2174/156652407783220732. PMID 18331228.
  6. ^ Yaylayan, Varoujan A.; Huyghues-Despointes, Alexis (1994). "Chemistry of Amadori Rearrangement Products: Analysis, Synthesis, Kinetics, Reactions, and Spectroscopic Properties". Critical Reviews in Food Science and Nutrition. 34 (4): 321–69. doi:10.1080/10408399409527667. PMID 7945894.
  7. ^ Bellier, Justine; Nokin, Marie-Julie; Lardé, Eva; Karoyan, Philippe; Peulen, Olivier; Castronovo, Vincent; Bellahcène, Akeila (2019). "Methylglyoxal, a Potent Inducer of AGEs, Connects between Diabetes and Cancer". Diabetes Research and Clinical Practice. 148: 200–211. doi:10.1016/j.diabres.2019.01.002. PMID 30664892. S2CID 58631777.
  8. ^ McPherson JD, Shilton BH, Walton DJ (March 1988). "Role of fructose in glycation and cross-linking of proteins". Biochemistry. 27 (6): 1901–7. doi:10.1021/bi00406a016. PMID 3132203.
  9. ^ Münch, Gerald; et al. (27 February 1997). "Influence of advanced glycation end-products and AGE-inhibitors on nucleation-dependent polymerization of β-amyloid peptide". Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease. 1360 (1): 17–29. doi:10.1016/S0925-4439(96)00062-2. PMID 9061036.
  10. ^ Munch, G; Deuther-Conrad W; Gasic-Milenkovic J. (2002). "Glycoxidative stress creates a vicious cycle of neurodegeneration in Alzheimer's disease--a target for neuroprotective treatment strategies?". J Neural Transm Suppl. 62 (62): 303–307. doi:10.1007/978-3-7091-6139-5_28. PMID 12456073.
  11. ^ Soldatos, G.; Cooper ME (Dec 2006). "Advanced glycation end products and vascular structure and function". Curr Hypertens Rep. 8 (6): 472–478. doi:10.1007/s11906-006-0025-8. PMID 17087858. S2CID 31239347.
  12. ^ Lee, J. Michael; Samuel P. Veres (2019-04-02). "Advanced glycation end-product cross-linking inhibits biomechanical plasticity and characteristic failure morphology of native tendon". Journal of Applied Physiology. 126 (4): 832–841. doi:10.1152/japplphysiol.00430.2018. PMC 6485690. PMID 30653412.
  13. ^ a b c Richarme G, Liu C, Mihoub M, Abdallah J, Leger T, Joly N, Liebart JC, Jurkunas UV, Nadal M, Bouloc P, Dairou J, Lamouri A. Guanine glycation repair by DJ-1/Park7 and its bacterial homologs. Science. 2017 Jul 14;357(6347):208-211. doi: 10.1126/science.aag1095. Epub 2017 Jun 8. PMID: 28596309

February 16, 2024
glycation, confused, with, glycosylation, enzymatic, glycosylation, covalent, attachment, sugar, protein, lipid, nucleic, acid, molecule, typical, sugars, that, participate, glycation, glucose, fructose, their, derivatives, enzymatic, process, responsible, man. Not to be confused with Glycosylation Glycation non enzymatic glycosylation is the covalent attachment of a sugar to a protein lipid or nucleic acid molecule 1 Typical sugars that participate in glycation are glucose fructose and their derivatives Glycation is the non enzymatic process responsible for many e g micro and macrovascular complications in diabetes mellitus and is implicated in some diseases and in aging 2 3 4 Glycation end products are believed to play a causative role in the vascular complications of diabetes mellitus 5 In contrast with glycation glycosylation is the enzyme mediated ATP dependent attachment of sugars to protein or lipid 1 Glycosylation occurs at defined sites on the target molecule It is a common form of post translational modification of proteins and is required for the functioning of the mature protein Contents 1 Biochemistry 2 Biomedical implications 3 DNA glycation 4 See also 5 Additional reading 6 ReferencesBiochemistry edit nbsp Glycation pathway via Amadori rearrangement in HbA1c R is typically N terminal valine 6 nbsp Imidazolones R CH2CH OH CH OH CH2OH are typical glycation products They arise by the condensation of 3 deoxyglucosone with the guanidine group of an arginine residue 7 Glycations occur mainly in the bloodstream to a small proportion of the absorbed simple sugars glucose fructose and galactose It appears that fructose has approximately ten times the glycation activity of glucose the primary body fuel 8 Glycation can occur through Amadori reactions Schiff base reactions and Maillard reactions which lead to advanced glycation end products AGEs 1 Biomedical implications editRed blood cells have a consistent lifespan of 120 days and are accessible for measurement of glycated hemoglobin Measurement of HbA1c the predominant form of glycated hemoglobin enables medium term blood sugar control to be monitored in diabetes Some glycation products are implicated in many age related chronic diseases including cardiovascular diseases the endothelium fibrinogen and collagen are damaged and Alzheimer s disease amyloid proteins are side products of the reactions progressing to AGEs 9 10 Long lived cells such as nerves and different types of brain cell long lasting proteins such as crystallins of the lens and cornea and DNA can sustain substantial glycation over time Damage by glycation results in stiffening of the collagen in the blood vessel walls leading to high blood pressure especially in diabetes 11 Glycations also cause weakening of the collagen in the blood vessel walls 12 which may lead to micro or macro aneurysm this may cause strokes if in the brain DNA glycation editThe term DNA glycation applies to DNA damage induced by reactive carbonyls principally methylglyoxal and glyoxal that are present in cells as by products of sugar metabolism 13 Glycation of DNA can cause mutation breaks in DNA and cytotoxicity 13 Guanine in DNA is the base most susceptible to glycation Glycated DNA as a form of damage appears to be as frequent as the more well studied oxidative DNA damage A protein designated DJ 1 also known as PARK7 is employed in the repair of glycated DNA bases in humans and homologs of this protein have also been identified in bacteria 13 See also editAdvanced glycation end product Alagebrium Fructose Galactose Glucose Glycosylation Glycated hemoglobin List of aging processesAdditional reading editAhmed N Furth AJ July 1992 Failure of common glycation assays to detect glycation by fructose Clin Chem 38 7 1301 3 doi 10 1093 clinchem 38 7 1301 PMID 1623595 Vlassara H June 2005 Advanced glycation in health and disease role of the modern environment Annals of the New York Academy of Sciences 1043 1 452 60 Bibcode 2005NYASA1043 452V doi 10 1196 annals 1333 051 PMID 16037266 S2CID 20952378 References edit a b c Lima M Baynes J W 2013 01 01 Glycation in Lennarz William J Lane M Daniel eds Encyclopedia of Biological Chemistry Second Edition Waltham Academic Press pp 405 411 doi 10 1016 b978 0 12 378630 2 00120 1 ISBN 978 0 12 378631 9 retrieved 2020 12 16 Glenn J Stitt A 2009 The role of advanced glycation end products in retinal ageing and disease Biochimica et Biophysica Acta BBA General Subjects 1790 10 1109 1116 doi 10 1016 j bbagen 2009 04 016 PMID 19409449 Semba R D Ferrucci L Sun K Beck J Dalal M Varadhan R Walston J Guralnik J M Fried L P 2009 Advanced glycation end products and their circulating receptors predict cardiovascular disease mortality in older community dwelling women Aging Clinical and Experimental Research 21 2 182 190 doi 10 1007 BF03325227 PMC 2684987 PMID 19448391 Semba R Najjar S Sun K Lakatta E Ferrucci L 2009 Serum carboxymethyl lysine an advanced glycation end product is associated with increased aortic pulse wave velocity in adults American Journal of Hypertension 22 1 74 79 doi 10 1038 ajh 2008 320 PMC 2637811 PMID 19023277 Yan S F D Agati V Schmidt A M Ramasamy R 2007 Receptor for Advanced Glycation Endproducts RAGE a formidable force in the pathogenesis of the cardiovascular complications of diabetes amp aging Current Molecular Medicine 7 8 699 710 doi 10 2174 156652407783220732 PMID 18331228 Yaylayan Varoujan A Huyghues Despointes Alexis 1994 Chemistry of Amadori Rearrangement Products Analysis Synthesis Kinetics Reactions and Spectroscopic Properties Critical Reviews in Food Science and Nutrition 34 4 321 69 doi 10 1080 10408399409527667 PMID 7945894 Bellier Justine Nokin Marie Julie Larde Eva Karoyan Philippe Peulen Olivier Castronovo Vincent Bellahcene Akeila 2019 Methylglyoxal a Potent Inducer of AGEs Connects between Diabetes and Cancer Diabetes Research and Clinical Practice 148 200 211 doi 10 1016 j diabres 2019 01 002 PMID 30664892 S2CID 58631777 McPherson JD Shilton BH Walton DJ March 1988 Role of fructose in glycation and cross linking of proteins Biochemistry 27 6 1901 7 doi 10 1021 bi00406a016 PMID 3132203 Munch Gerald et al 27 February 1997 Influence of advanced glycation end products and AGE inhibitors on nucleation dependent polymerization of b amyloid peptide Biochimica et Biophysica Acta BBA Molecular Basis of Disease 1360 1 17 29 doi 10 1016 S0925 4439 96 00062 2 PMID 9061036 Munch G Deuther Conrad W Gasic Milenkovic J 2002 Glycoxidative stress creates a vicious cycle of neurodegeneration in Alzheimer s disease a target for neuroprotective treatment strategies J Neural Transm Suppl 62 62 303 307 doi 10 1007 978 3 7091 6139 5 28 PMID 12456073 Soldatos G Cooper ME Dec 2006 Advanced glycation end products and vascular structure and function Curr Hypertens Rep 8 6 472 478 doi 10 1007 s11906 006 0025 8 PMID 17087858 S2CID 31239347 Lee J Michael Samuel P Veres 2019 04 02 Advanced glycation end product cross linking inhibits biomechanical plasticity and characteristic failure morphology of native tendon Journal of Applied Physiology 126 4 832 841 doi 10 1152 japplphysiol 00430 2018 PMC 6485690 PMID 30653412 a b c Richarme G Liu C Mihoub M Abdallah J Leger T Joly N Liebart JC Jurkunas UV Nadal M Bouloc P Dairou J Lamouri A Guanine glycation repair by DJ 1 Park7 and its bacterial homologs Science 2017 Jul 14 357 6347 208 211 doi 10 1126 science aag1095 Epub 2017 Jun 8 PMID 28596309 Retrieved from https en wikipedia org w index php title Glycation amp oldid 1171210108, wikipedia, wiki, book, books, library,

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