{"corpus_id":25524766,"paper_sha":"f11ad44cef704f0d4aa500970e87d1288e1cb0a6","doi":"10.1074/JBC.M309090200","arxiv_id":null,"pmid":14634019,"pmcid":null,"mag_id":2010261765,"dblp_id":null,"acl_id":null,"title":"2-Ammonio-6-(3-oxidopyridinium-1-yl)hexanoate (OP-lysine) Is a Newly Identified Advanced Glycation End Product in Cataractous and Aged Human Lenses*","year":2004,"publication_date":"2004-02-20","venue":"Journal of Biological Chemistry","journal":{"name":"Journal of Biological Chemistry","pages":"6487 - 6495","volume":"279"},"journal_issn":null,"journal_title":null,"publication_types":["JournalArticle"],"pubmed_pub_types":["Journal Article","Research Support, Non-U.S. Gov't","Research Support, U.S. Gov't, P.H.S."],"s2_fields_of_study":["Biology","Medicine","Chemistry"],"reference_count":31,"citation_count":60,"influential_citation_count":0,"is_open_access":true,"arxiv_categories":null,"arxiv_license":null,"arxiv_journal_ref":null,"mesh_headings":[{"d":"Aged","mj":false,"ui":"D000368"},{"d":"Aging","mj":false,"ui":"D000375"},{"d":"Ascorbic Acid","mj":false,"qs":[{"q":"chemistry","mj":false,"ui":"Q000737"}],"ui":"D001205"},{"d":"Caproates","mj":false,"qs":[{"q":"chemistry","mj":true,"ui":"Q000737"},{"q":"metabolism","mj":false,"ui":"Q000378"}],"ui":"D002208"},{"d":"Cataract","mj":false,"qs":[{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D002386"},{"d":"Chromatography, High Pressure Liquid","mj":false,"ui":"D002851"},{"d":"Chromatography, Ion Exchange","mj":false,"ui":"D002852"},{"d":"Glycation End Products, Advanced","mj":true,"qs":[{"q":"chemistry","mj":true,"ui":"Q000737"}],"ui":"D017127"},{"d":"Humans","mj":false,"ui":"D006801"},{"d":"Hydrolysis","mj":false,"ui":"D006868"},{"d":"Lens, Crystalline","mj":false,"qs":[{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D007908"},{"d":"Light","mj":false,"ui":"D008027"},{"d":"Lysine","mj":false,"qs":[{"q":"analogs & derivatives","mj":false,"ui":"Q000031"},{"q":"chemistry","mj":true,"ui":"Q000737"},{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D008239"},{"d":"Magnetic Resonance Spectroscopy","mj":false,"ui":"D009682"},{"d":"Middle Aged","mj":false,"ui":"D008875"},{"d":"Models, Chemical","mj":false,"ui":"D008956"},{"d":"Pyridinium Compounds","mj":false,"qs":[{"q":"chemistry","mj":true,"ui":"Q000737"},{"q":"metabolism","mj":true,"ui":"Q000378"}],"ui":"D011726"},{"d":"Time Factors","mj":false,"ui":"D013997"},{"d":"Ultraviolet Rays","mj":false,"ui":"D014466"},{"d":"Water","mj":false,"qs":[{"q":"chemistry","mj":false,"ui":"Q000737"}],"ui":"D014867"}],"chemicals":[{"n":"2-amino-6-(3-oxidopyridinium-1-yl)hexanoic acid","ui":"C484321","reg":"0"},{"n":"Caproates","ui":"D002208","reg":"0"},{"n":"Glycation End Products, Advanced","ui":"D017127","reg":"0"},{"n":"Pyridinium Compounds","ui":"D011726","reg":"0"},{"n":"Water","ui":"D014867","reg":"059QF0KO0R"},{"n":"hexanoic acid","ui":"C037652","reg":"1F8SN134MX"},{"n":"Lysine","ui":"D008239","reg":"K3Z4F929H6"},{"n":"Ascorbic Acid","ui":"D001205","reg":"PQ6CK8PD0R"}],"comments_corrections":null,"source_flags":5,"s2_open_access_pdf_url":"http://www.jbc.org/article/S0021925818445991/pdf","s2_open_access_landing_url":"https://www.semanticscholar.org/paper/f11ad44cef704f0d4aa500970e87d1288e1cb0a6","s2_open_access_license":"CCBY","s2_open_access_status":"HYBRID","pmc_open_access_pdf_url":null,"pmc_open_access_landing_url":null,"pmc_open_access_license":null,"pmc_open_access_status":null,"unpaywall_open_access_pdf_url":null,"unpaywall_open_access_landing_url":null,"unpaywall_open_access_license":null,"unpaywall_open_access_status":null,"abstract":"Post-translational modifications of proteins take place during the aging of human lens. The present study describes a newly isolated glycation product of lysine, which was found in the human lens. Cataractous and aged human lenses were hydrolyzed and fractionated using reverse-phase and ion-exchange high performance liquid chromatography (HPLC). One of the nonproteinogenic amino acid components of the hydrolysates was identified as a 3-hydroxypyridinium derivative of lysine, 2-ammonio-6-(3-oxidopyridinium-1-yl)hexanoate (OP-lysine). The compound was synthesized independently from 3-hydroxypyridine and methyl 2-[(tert-butoxycarbonyl)amino]-6-iodohexanoate. The spectral and chromatographic properties of the synthetic OP-lysine and the substance isolated from hydrolyzed lenses were identical. HPLC analysis showed that the amounts of OP-lysine were higher in water-insoluble compared with water-soluble proteins and was higher in a pool of cataractous lenses compared with normal aged lenses, reaching 500 pmol/mg protein. The model incubations showed that an anaerobic reaction mixture of Nα-tert-butoxycarbonyllysine, glycolaldehyde, and glyceraldehyde could produce the Nα-t-butoxycarbonyl derivative of OP-lysine. The irradiation of OP-lysine with UVA under anaerobic conditions in the presence of ascorbate led to a photochemical bleaching of this compound. Our results argue that OP-lysine is a newly identified glycation product of lysine in the lens. It is a marker of aging and pathology of the lens, and its formation could be considered as a potential cataract risk-factor based on its concentration and its photochemical properties.","claims":[{"public_id":"cl_3c2654673b1c7e4025be71d22fbc51ae","status":"active","text":"An anaerobic incubation of Nα-tert-butoxycarbonyllysine, glycolaldehyde, and glyceraldehyde produced the Nα-t-butoxycarbonyl derivative of OP-lysine.","confidence":0.95,"contributors":[{"id":1,"public_id":"12632b8b5f","public_label":"Anonymous (12632b8b5f)","roles":["extraction"],"url":"https://sah.borca.ai/u/12632b8b5f"}],"url":"https://sah.borca.ai/claims/cl_3c2654673b1c7e4025be71d22fbc51ae"},{"public_id":"cl_ef396a6dc59ffb041d48275c0b98a0c9","status":"active","text":"OP-lysine levels were higher in water-insoluble proteins than in water-soluble proteins and were elevated in cataractous lenses compared with normal aged lenses, reaching 500 pmol/mg 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