(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid

(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid

Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified u...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2019-03, Vol.84 (6), p.3552-3558
Hauptverfasser: Iida, Sayaka, Yamamoto, Yorihiro, Fujisawa, Akio
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3558
container_issue 6
container_start_page 3552
container_title Journal of organic chemistry
container_volume 84
creator Iida, Sayaka
Yamamoto, Yorihiro
Fujisawa, Akio
description Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified unknown intermediates as (2,5-dioxoimidazolidin-4-ylidene)­aminocarbonylcarbamic acid (DIAA), dehydroallantoin, and 4-hydroxyallantoin (4-HAL). DIAA is the key to PA production, and its formation pathway was characterized using 18O2 and H2 18O. Two oxygen atoms were confirmed to be incorporated into DIAA: the 5-oxo- oxygen from singlet oxygen and the carboxylic oxygen from water. Isolated DIAA and 4-HAL gave PA stoichiometrically. A plausible reaction scheme in which two pathways branch out from DIAA is presented, and the potential for PA as an endogenous probe for biological formation of singlet oxygen is discussed.
doi_str_mv 10.1021/acs.joc.9b00163
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2186617072</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2186617072</sourcerecordid><originalsourceid>FETCH-LOGICAL-a333t-384f7fde98a68aaaf4984953fba7f4514f831b319c095cf3a19a5cc6a4057fc73</originalsourceid><addsrcrecordid>eNp1kUtPxCAYRYnR6PhYuzMsNcoIpfSxnPhOTMZEXTdfKSimhRHaZMZf4s-VyVR3svkIOfcQuAgdMzplNGGXIMP0w8lpWVPKMr6FJkwklGQlTbfRhNIkITzJ-B7aD-GDxiWE2EV7nBY0Z4JN0PdpciHItXFLZzrTwJdrTWMsSckqbpRVZ9AZ6yT42tlVu57xQOKZNA2GgAE_eSUHH5zHTuMn8FCDHYEL3L8r_GzsW6t6PF-u3pQlzwsljY7EfBnv642zUeGaQfZrwasfs4doR0Mb1NE4D9Dr7c3L1T15nN89XM0eCXDOe8KLVOe6UWUBWQEAOi2LtBRc15DrVLBUF5zVnJWSlkJqDqwEIWUGKRW5ljk_QKcb78K7z0GFvupMkKptwSo3hCphRZaxnOZJRC83qPQuBK90tfCmA7-qGK3WdVSxjirWUY11xMTJKB_qTjV__O__R-B8A2ySg7fxrf_qfgDMNZa2</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2186617072</pqid></control><display><type>article</type><title>(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid</title><source>ACS Publications</source><creator>Iida, Sayaka ; Yamamoto, Yorihiro ; Fujisawa, Akio</creator><creatorcontrib>Iida, Sayaka ; Yamamoto, Yorihiro ; Fujisawa, Akio</creatorcontrib><description>Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified unknown intermediates as (2,5-dioxoimidazolidin-4-ylidene)­aminocarbonylcarbamic acid (DIAA), dehydroallantoin, and 4-hydroxyallantoin (4-HAL). DIAA is the key to PA production, and its formation pathway was characterized using 18O2 and H2 18O. Two oxygen atoms were confirmed to be incorporated into DIAA: the 5-oxo- oxygen from singlet oxygen and the carboxylic oxygen from water. Isolated DIAA and 4-HAL gave PA stoichiometrically. A plausible reaction scheme in which two pathways branch out from DIAA is presented, and the potential for PA as an endogenous probe for biological formation of singlet oxygen is discussed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.9b00163</identifier><identifier>PMID: 30807151</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2019-03, Vol.84 (6), p.3552-3558</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a333t-384f7fde98a68aaaf4984953fba7f4514f831b319c095cf3a19a5cc6a4057fc73</citedby><cites>FETCH-LOGICAL-a333t-384f7fde98a68aaaf4984953fba7f4514f831b319c095cf3a19a5cc6a4057fc73</cites><orcidid>0000-0001-7223-324X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.9b00163$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.9b00163$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30807151$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Iida, Sayaka</creatorcontrib><creatorcontrib>Yamamoto, Yorihiro</creatorcontrib><creatorcontrib>Fujisawa, Akio</creatorcontrib><title>(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified unknown intermediates as (2,5-dioxoimidazolidin-4-ylidene)­aminocarbonylcarbamic acid (DIAA), dehydroallantoin, and 4-hydroxyallantoin (4-HAL). DIAA is the key to PA production, and its formation pathway was characterized using 18O2 and H2 18O. Two oxygen atoms were confirmed to be incorporated into DIAA: the 5-oxo- oxygen from singlet oxygen and the carboxylic oxygen from water. Isolated DIAA and 4-HAL gave PA stoichiometrically. A plausible reaction scheme in which two pathways branch out from DIAA is presented, and the potential for PA as an endogenous probe for biological formation of singlet oxygen is discussed.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kUtPxCAYRYnR6PhYuzMsNcoIpfSxnPhOTMZEXTdfKSimhRHaZMZf4s-VyVR3svkIOfcQuAgdMzplNGGXIMP0w8lpWVPKMr6FJkwklGQlTbfRhNIkITzJ-B7aD-GDxiWE2EV7nBY0Z4JN0PdpciHItXFLZzrTwJdrTWMsSckqbpRVZ9AZ6yT42tlVu57xQOKZNA2GgAE_eSUHH5zHTuMn8FCDHYEL3L8r_GzsW6t6PF-u3pQlzwsljY7EfBnv642zUeGaQfZrwasfs4doR0Mb1NE4D9Dr7c3L1T15nN89XM0eCXDOe8KLVOe6UWUBWQEAOi2LtBRc15DrVLBUF5zVnJWSlkJqDqwEIWUGKRW5ljk_QKcb78K7z0GFvupMkKptwSo3hCphRZaxnOZJRC83qPQuBK90tfCmA7-qGK3WdVSxjirWUY11xMTJKB_qTjV__O__R-B8A2ySg7fxrf_qfgDMNZa2</recordid><startdate>20190315</startdate><enddate>20190315</enddate><creator>Iida, Sayaka</creator><creator>Yamamoto, Yorihiro</creator><creator>Fujisawa, Akio</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7223-324X</orcidid></search><sort><creationdate>20190315</creationdate><title>(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid</title><author>Iida, Sayaka ; Yamamoto, Yorihiro ; Fujisawa, Akio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a333t-384f7fde98a68aaaf4984953fba7f4514f831b319c095cf3a19a5cc6a4057fc73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Iida, Sayaka</creatorcontrib><creatorcontrib>Yamamoto, Yorihiro</creatorcontrib><creatorcontrib>Fujisawa, Akio</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Iida, Sayaka</au><au>Yamamoto, Yorihiro</au><au>Fujisawa, Akio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2019-03-15</date><risdate>2019</risdate><volume>84</volume><issue>6</issue><spage>3552</spage><epage>3558</epage><pages>3552-3558</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Previously, we identified that parabanic acid (PA) and its hydrolysate, oxaluric acid (OUA), are the singlet oxygen-specific oxidation products of uric acid (UA). In this study, we investigated the PA formation mechanism by using HPLC and a time-of-flight mass spectrometry technique and identified unknown intermediates as (2,5-dioxoimidazolidin-4-ylidene)­aminocarbonylcarbamic acid (DIAA), dehydroallantoin, and 4-hydroxyallantoin (4-HAL). DIAA is the key to PA production, and its formation pathway was characterized using 18O2 and H2 18O. Two oxygen atoms were confirmed to be incorporated into DIAA: the 5-oxo- oxygen from singlet oxygen and the carboxylic oxygen from water. Isolated DIAA and 4-HAL gave PA stoichiometrically. A plausible reaction scheme in which two pathways branch out from DIAA is presented, and the potential for PA as an endogenous probe for biological formation of singlet oxygen is discussed.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>30807151</pmid><doi>10.1021/acs.joc.9b00163</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-7223-324X</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2019-03, Vol.84 (6), p.3552-3558
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2186617072
source ACS Publications
title (2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic Acid as a Precursor of Parabanic Acid, the Singlet Oxygen-Specific Oxidation Product of Uric Acid
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T12%3A42%3A19IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=(2,5-Dioxoimidazolidin-4-ylidene)aminocarbonylcarbamic%20Acid%20as%20a%20Precursor%20of%20Parabanic%20Acid,%20the%20Singlet%20Oxygen-Specific%20Oxidation%20Product%20of%20Uric%20Acid&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Iida,%20Sayaka&rft.date=2019-03-15&rft.volume=84&rft.issue=6&rft.spage=3552&rft.epage=3558&rft.pages=3552-3558&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.9b00163&rft_dat=%3Cproquest_cross%3E2186617072%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2186617072&rft_id=info:pmid/30807151&rfr_iscdi=true