Identification of 3,4-Dihydroxy-2-oxo-butanal (L-threosone) as an Intermediate Compound in Oxidative Degradation of Dehydro-L-ascorbic Acid and 2,3-Diketo-L-gulonic Acid in a Deuterium Oxide Phosphate Buffer
Dehydro-L-ascorbic acid (DAA), an oxidation product of L-ascorbic acid (vitamin C), is unstable in the neutral and basic pH regions. When DAA was incubated in a phosphate buffer with deuterium oxide (pH 7.4), it was degraded to form the main degradation compound, which was identified as 3,4-dihydrox...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2001-08, Vol.65 (8), p.1707-1712 |
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| creator | NISHIKAWA, Yoko TOYOSHIMA, Yuka KURATA, Tadao |
| description | Dehydro-L-ascorbic acid (DAA), an oxidation product of L-ascorbic acid (vitamin C), is unstable in the neutral and basic pH regions. When DAA was incubated in a phosphate buffer with deuterium oxide (pH 7.4), it was degraded to form the main degradation compound, which was identified as 3,4-dihydroxy-2-oxo-butanal (L-threosone). This compound was also formed from diketo-L-gulonic acid (DKG) in a phosphate buffer with deuterium oxide. L-threosone had reducing activity, probably due to its enolization, and is likely to have been involved in the formation of the reducing activity that was observed in aqueous DAA and DKG solutions. As a reactive dicarbonyl compound, L-threosone might also take some role in the cross-linking of tissue proteins that are formed in vivo in the Maillard reaction. |
| doi_str_mv | 10.1271/bbb.65.1707 |
| format | Article |
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When DAA was incubated in a phosphate buffer with deuterium oxide (pH 7.4), it was degraded to form the main degradation compound, which was identified as 3,4-dihydroxy-2-oxo-butanal (L-threosone). This compound was also formed from diketo-L-gulonic acid (DKG) in a phosphate buffer with deuterium oxide. L-threosone had reducing activity, probably due to its enolization, and is likely to have been involved in the formation of the reducing activity that was observed in aqueous DAA and DKG solutions. As a reactive dicarbonyl compound, L-threosone might also take some role in the cross-linking of tissue proteins that are formed in vivo in the Maillard reaction.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1271/bbb.65.1707</identifier><identifier>PMID: 11577707</identifier><language>eng</language><publisher>Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry</publisher><subject>2,3-Diketogulonic Acid - chemistry ; Aldehydes - chemistry ; Analytical, structural and metabolic biochemistry ; Biological and medical sciences ; Buffers ; Chromatography, Liquid ; Coenzymes, vitamins ; degradation ; Dehydroascorbic Acid - chemistry ; Deuterium Oxide - chemistry ; diketo-L-gulonic acid ; Fundamental and applied biological sciences. Psychology ; Hydrazones - chemistry ; L-ascorbic acid ; L-threosone ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Molecular Weight ; Other biological molecules ; Oxalic Acid - chemistry ; Oxidation-Reduction ; Phosphates ; Spectrometry, Mass, Fast Atom Bombardment ; Spectrophotometry, Ultraviolet</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2001-08, Vol.65 (8), p.1707-1712</ispartof><rights>2001 by Japan Society for Bioscience, Biotechnology, and Agrochemistry 2001</rights><rights>2002 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2001</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c619t-e5d48685598e494d9bcdcf6d7432ea89dc70c5fb88caff35bea15d42036cd3133</citedby><cites>FETCH-LOGICAL-c619t-e5d48685598e494d9bcdcf6d7432ea89dc70c5fb88caff35bea15d42036cd3133</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14141834$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11577707$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>NISHIKAWA, Yoko</creatorcontrib><creatorcontrib>TOYOSHIMA, Yuka</creatorcontrib><creatorcontrib>KURATA, Tadao</creatorcontrib><title>Identification of 3,4-Dihydroxy-2-oxo-butanal (L-threosone) as an Intermediate Compound in Oxidative Degradation of Dehydro-L-ascorbic Acid and 2,3-Diketo-L-gulonic Acid in a Deuterium Oxide Phosphate Buffer</title><title>Bioscience, biotechnology, and biochemistry</title><addtitle>Biosci Biotechnol Biochem</addtitle><description>Dehydro-L-ascorbic acid (DAA), an oxidation product of L-ascorbic acid (vitamin C), is unstable in the neutral and basic pH regions. When DAA was incubated in a phosphate buffer with deuterium oxide (pH 7.4), it was degraded to form the main degradation compound, which was identified as 3,4-dihydroxy-2-oxo-butanal (L-threosone). This compound was also formed from diketo-L-gulonic acid (DKG) in a phosphate buffer with deuterium oxide. L-threosone had reducing activity, probably due to its enolization, and is likely to have been involved in the formation of the reducing activity that was observed in aqueous DAA and DKG solutions. As a reactive dicarbonyl compound, L-threosone might also take some role in the cross-linking of tissue proteins that are formed in vivo in the Maillard reaction.</description><subject>2,3-Diketogulonic Acid - chemistry</subject><subject>Aldehydes - chemistry</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Biological and medical sciences</subject><subject>Buffers</subject><subject>Chromatography, Liquid</subject><subject>Coenzymes, vitamins</subject><subject>degradation</subject><subject>Dehydroascorbic Acid - chemistry</subject><subject>Deuterium Oxide - chemistry</subject><subject>diketo-L-gulonic acid</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Hydrazones - chemistry</subject><subject>L-ascorbic acid</subject><subject>L-threosone</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Molecular Weight</subject><subject>Other biological molecules</subject><subject>Oxalic Acid - chemistry</subject><subject>Oxidation-Reduction</subject><subject>Phosphates</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkV9v0zAUxSMEYmXwxDuyhEAg5hLHdpw8bi1_KlUaD_AcOfb16pHYnZ2w9lPylXDWjkkI-cGS7--eY52TZS9JPieFIB_btp2XfE5ELh5lM0KZwGXNxONsltekxBXj5CR7FuN1nqcHTp5mJ4RwIRI_y36vNLjBGqvkYL1D3iB6xvDSbvY6-N0eF9jvPG7HQTrZoXdrPGwC-OgdvEcyIunQyg0QetBWDoAWvt_60WlkHbrcWZ1UfwFawlWQ-q_DEu7U8RrLqHxorULnyuokplFxRpP7Txim8dXYeXc_TYoyrY7JzY79nTqgbxsft5vJ-WI0BsLz7ImRXYQXx_s0-_H50_fFV7y-_LJanK-xKkk9YOCaVWXFeV0Bq5muW6WVKbVgtABZ1VqJXHHTVpWSxlDegiRppchpqTQllJ5mbw-62-BvRohD09uooOukAz_GRpAiF4xP4Ot_wGs_hpRlbAhL1oyVtEjUhwOlgo8xgGm2wfYy7BuSN1PLTWq5KXkztZzoV0fNsU3BP7DHWhPw5gikgGVngnTKxgeOpVNRlrjywFlnfOjlrQ-dbga573y4X6L_-8EfDUXDUw</recordid><startdate>20010801</startdate><enddate>20010801</enddate><creator>NISHIKAWA, Yoko</creator><creator>TOYOSHIMA, Yuka</creator><creator>KURATA, Tadao</creator><general>Japan Society for Bioscience, Biotechnology, and Agrochemistry</general><general>Japan Society for Bioscience Biotechnology and Agrochemistry</general><general>Oxford University Press</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20010801</creationdate><title>Identification of 3,4-Dihydroxy-2-oxo-butanal (L-threosone) as an Intermediate Compound in Oxidative Degradation of Dehydro-L-ascorbic Acid and 2,3-Diketo-L-gulonic Acid in a Deuterium Oxide Phosphate Buffer</title><author>NISHIKAWA, Yoko ; TOYOSHIMA, Yuka ; KURATA, Tadao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c619t-e5d48685598e494d9bcdcf6d7432ea89dc70c5fb88caff35bea15d42036cd3133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>2,3-Diketogulonic Acid - chemistry</topic><topic>Aldehydes - chemistry</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Biological and medical sciences</topic><topic>Buffers</topic><topic>Chromatography, Liquid</topic><topic>Coenzymes, vitamins</topic><topic>degradation</topic><topic>Dehydroascorbic Acid - chemistry</topic><topic>Deuterium Oxide - chemistry</topic><topic>diketo-L-gulonic acid</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Hydrazones - chemistry</topic><topic>L-ascorbic acid</topic><topic>L-threosone</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Molecular Weight</topic><topic>Other biological molecules</topic><topic>Oxalic Acid - chemistry</topic><topic>Oxidation-Reduction</topic><topic>Phosphates</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>NISHIKAWA, Yoko</creatorcontrib><creatorcontrib>TOYOSHIMA, Yuka</creatorcontrib><creatorcontrib>KURATA, Tadao</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>NISHIKAWA, Yoko</au><au>TOYOSHIMA, Yuka</au><au>KURATA, Tadao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of 3,4-Dihydroxy-2-oxo-butanal (L-threosone) as an Intermediate Compound in Oxidative Degradation of Dehydro-L-ascorbic Acid and 2,3-Diketo-L-gulonic Acid in a Deuterium Oxide Phosphate Buffer</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><addtitle>Biosci Biotechnol Biochem</addtitle><date>2001-08-01</date><risdate>2001</risdate><volume>65</volume><issue>8</issue><spage>1707</spage><epage>1712</epage><pages>1707-1712</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>Dehydro-L-ascorbic acid (DAA), an oxidation product of L-ascorbic acid (vitamin C), is unstable in the neutral and basic pH regions. When DAA was incubated in a phosphate buffer with deuterium oxide (pH 7.4), it was degraded to form the main degradation compound, which was identified as 3,4-dihydroxy-2-oxo-butanal (L-threosone). This compound was also formed from diketo-L-gulonic acid (DKG) in a phosphate buffer with deuterium oxide. L-threosone had reducing activity, probably due to its enolization, and is likely to have been involved in the formation of the reducing activity that was observed in aqueous DAA and DKG solutions. As a reactive dicarbonyl compound, L-threosone might also take some role in the cross-linking of tissue proteins that are formed in vivo in the Maillard reaction.</abstract><cop>Tokyo</cop><pub>Japan Society for Bioscience, Biotechnology, and Agrochemistry</pub><pmid>11577707</pmid><doi>10.1271/bbb.65.1707</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | Bioscience, biotechnology, and biochemistry, 2001-08, Vol.65 (8), p.1707-1712 |
| issn | 0916-8451 1347-6947 |
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| source | Oxford University Press Journals All Titles (1996-Current); MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Open Access Titles of Japan; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | 2,3-Diketogulonic Acid - chemistry Aldehydes - chemistry Analytical, structural and metabolic biochemistry Biological and medical sciences Buffers Chromatography, Liquid Coenzymes, vitamins degradation Dehydroascorbic Acid - chemistry Deuterium Oxide - chemistry diketo-L-gulonic acid Fundamental and applied biological sciences. Psychology Hydrazones - chemistry L-ascorbic acid L-threosone Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Weight Other biological molecules Oxalic Acid - chemistry Oxidation-Reduction Phosphates Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Ultraviolet |
| title | Identification of 3,4-Dihydroxy-2-oxo-butanal (L-threosone) as an Intermediate Compound in Oxidative Degradation of Dehydro-L-ascorbic Acid and 2,3-Diketo-L-gulonic Acid in a Deuterium Oxide Phosphate Buffer |
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