Allysine is a derivative of lysine, used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin.[1]
Large quantities of elastin and collagen present in tissue may lead to metastasis: spread of disease. Fibrous tissue containing oxidized collagen may result in a condition known as fibrosis. The oxidation of lysine residues present in collagen creates the aldehyde, aminoadipic-δ-semialdehyde (allysine). Increased allysine concentration in tissues has been correlated to the presence of fibrosis.[2] To qualify protein carbonyls in biological systems, most research studies use the dinitrophenylhydrazine (DNPH) process. The study of particular protein carbonyls, such as allysine, reveals more about specific redox processes and mechanisms at the molecular level.[3] Allysine and its oxidation product, α- amino adipic acid (α-AA), have been discovered to also be diabetes risk indicators. To get a better understanding of this concept, human serum albumin was incubated for 32 hours at 37 degrees Celsius in the presence of FeCl3 (25 μM) and increasing glucose concentrations. Both allysine and α-AA levels were found to rise as glucose levels increased which lead to the depletion of tryptophan. Regarding the underlying functions of tryptophan and its metabolites, depletion of tryptophan and its metabolites may result in additional physiological problems such as coronary artery disease and neurological complications.[4]
Allysine quantification
Allysine can be reacted with sodium 2-naphthol-6-sulfonate to produce a fluorescent bis-naphtol allysine product. Allysine can then be quantified through use of high-performance liquid chromatography (HPLC). This method of detection was used to show that allysine has a 2.5 fold higher concentration in fibrotic vs. normal tissue.[5]
^Pinnell SR, Martin GR (October 1968). "The cross-linking of collagen and elastin: enzymatic conversion of lysine in peptide linkage to alpha-aminoadipic-delta-semialdehyde (allysine) by an extract from bone". Proceedings of the National Academy of Sciences of the United States of America. 61 (2): 708–16. Bibcode:1968PNAS...61..708P. doi:10.1073/pnas.61.2.708. PMC225217. PMID 5246001.
^Wahsner J, Désogère P, Abston E, Graham-O'Regan KA, Wang J, Rotile NJ, et al. (April 2019). "68Ga-NODAGA-Indole: An Allysine-Reactive Positron Emission Tomography Probe for Molecular Imaging of Pulmonary Fibrogenesis". Journal of the American Chemical Society. 141 (14): 5593–5596. doi:10.1021/jacs.8b12342. PMC6494104. PMID 30908032.
^Luna C, Estévez M (January 2019). "Formation of allysine in β-lactoglobulin and myofibrillar proteins by glyoxal and methylglyoxal: Impact on water-holding capacity and in vitro digestibility". Food Chemistry. 271: 87–93. doi:10.1016/j.foodchem.2018.07.167. PMID 30236745. S2CID 52309183.
^Luna C, Arjona A, Dueñas C, Estevez M (March 2021). "Allysine and α-Aminoadipic Acid as Markers of the Glyco-Oxidative Damage to Human Serum Albumin under Pathological Glucose Concentrations". Antioxidants. 10 (3): 474. doi:10.3390/antiox10030474. PMC8002732. PMID 33802856.
^Waghorn PA, Oliveira BL, Jones CM, Tager AM, Caravan P (October 2017). "High sensitivity HPLC method for determination of the allysine concentration in tissue by use of a naphthol derivative". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 1064: 7–13. doi:10.1016/j.jchromb.2017.08.032. PMC5662445. PMID 28886479.
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allysine, confused, with, allicin, derivative, lysine, used, production, elastin, collagen, produced, actions, enzyme, lysyl, oxidase, extracellular, matrix, essential, crosslink, formation, that, stabilizes, collagen, elastin, namespreferred, iupac, name, ami. Not to be confused with Allicin Allysine is a derivative of lysine used in the production of elastin and collagen It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin 1 Allysine NamesPreferred IUPAC name 2S 2 Amino 6 oxohexanoic acidOther names 2 aminoadipate semialdehyde 2 amino 5 formylvaleric acid norvaline 6 oxo DL norleucineIdentifiersCAS Number 1962 83 0 Y3D model JSmol Interactive imageInteractive imageChEBI CHEBI 57988 YChemSpider 202 YKEGG C04076 YMeSH allysinePubChem CID 207UNII 425I4Y24YZ YInChI InChI 1S C6H11NO3 c7 5 6 9 10 3 1 2 4 8 h4 5H 1 3 7H2 H 9 10 YKey GFXYTQPNNXGICT UHFFFAOYSA N YInChI 1 C6H11NO3 c7 5 6 9 10 3 1 2 4 8 h4 5H 1 3 7H2 H 9 10 t5 m0 s1Key GFXYTQPNNXGICT YFKPBYRVBJInChI 1 C6H11NO3 c7 5 6 9 10 3 1 2 4 8 h4 5H 1 3 7H2 H 9 10 Key GFXYTQPNNXGICT UHFFFAOYADSMILES O CCCC C H N C O OO CCCCC N C O OPropertiesChemical formula C 6H 11N O 3Molar mass 145 158 g mol 1Density 1 74g cm3Boiling point 295 2 C 563 4 F 568 3 K HazardsFlash point 132 3 C 270 1 F 405 4 K Except 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 Contents 1 Clinical relevance 2 Allysine quantification 3 See also 4 ReferencesClinical relevance EditLarge quantities of elastin and collagen present in tissue may lead to metastasis spread of disease Fibrous tissue containing oxidized collagen may result in a condition known as fibrosis The oxidation of lysine residues present in collagen creates the aldehyde aminoadipic d semialdehyde allysine Increased allysine concentration in tissues has been correlated to the presence of fibrosis 2 To qualify protein carbonyls in biological systems most research studies use the dinitrophenylhydrazine DNPH process The study of particular protein carbonyls such as allysine reveals more about specific redox processes and mechanisms at the molecular level 3 Allysine and its oxidation product a amino adipic acid a AA have been discovered to also be diabetes risk indicators To get a better understanding of this concept human serum albumin was incubated for 32 hours at 37 degrees Celsius in the presence of FeCl3 25 mM and increasing glucose concentrations Both allysine and a AA levels were found to rise as glucose levels increased which lead to the depletion of tryptophan Regarding the underlying functions of tryptophan and its metabolites depletion of tryptophan and its metabolites may result in additional physiological problems such as coronary artery disease and neurological complications 4 Allysine quantification EditAllysine can be reacted with sodium 2 naphthol 6 sulfonate to produce a fluorescent bis naphtol allysine product Allysine can then be quantified through use of high performance liquid chromatography HPLC This method of detection was used to show that allysine has a 2 5 fold higher concentration in fibrotic vs normal tissue 5 See also EditSaccharopineReferences Edit Pinnell SR Martin GR October 1968 The cross linking of collagen and elastin enzymatic conversion of lysine in peptide linkage to alpha aminoadipic delta semialdehyde allysine by an extract from bone Proceedings of the National Academy of Sciences of the United States of America 61 2 708 16 Bibcode 1968PNAS 61 708P doi 10 1073 pnas 61 2 708 PMC 225217 PMID 5246001 Wahsner J Desogere P Abston E Graham O Regan KA Wang J Rotile NJ et al April 2019 68Ga NODAGA Indole An Allysine Reactive Positron Emission Tomography Probe for Molecular Imaging of Pulmonary Fibrogenesis Journal of the American Chemical Society 141 14 5593 5596 doi 10 1021 jacs 8b12342 PMC 6494104 PMID 30908032 Luna C Estevez M January 2019 Formation of allysine in b lactoglobulin and myofibrillar proteins by glyoxal and methylglyoxal Impact on water holding capacity and in vitro digestibility Food Chemistry 271 87 93 doi 10 1016 j foodchem 2018 07 167 PMID 30236745 S2CID 52309183 Luna C Arjona A Duenas C Estevez M March 2021 Allysine and a Aminoadipic Acid as Markers of the Glyco Oxidative Damage to Human Serum Albumin under Pathological Glucose Concentrations Antioxidants 10 3 474 doi 10 3390 antiox10030474 PMC 8002732 PMID 33802856 Waghorn PA Oliveira BL Jones CM Tager AM Caravan P October 2017 High sensitivity HPLC method for determination of the allysine concentration in tissue by use of a naphthol derivative Journal of Chromatography B Analytical Technologies in the Biomedical and Life Sciences 1064 7 13 doi 10 1016 j jchromb 2017 08 032 PMC 5662445 PMID 28886479 This biochemistry article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Allysine amp oldid 1125336196, wikipedia, wiki, book, books, library,
