Photooxidation of hypotaurine taurine in the presence of flavins
Irradiation of organic sulfinates such as hypotaurine and cysteine sulfinic acid in the presence of catalytic amounts of flavins led to the oxidation of its sulfinic groups (-SO2H) to the corresponding sulfonates. The process of hypotaurine oxidation in the presence of riboflavin, followed by absorb...
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| Veröffentlicht in: | Journal of Nutritional Science and Vitaminology 1989, Vol.35(2), pp.143-153 |
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| container_end_page | 153 |
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| container_issue | 2 |
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| container_title | Journal of Nutritional Science and Vitaminology |
| container_volume | 35 |
| creator | Ricci, G. (University G. D'Annuzio, Chieti (Italy)) Chiaraluce, R Pitari, G Dupre, S Fujii, O Hosokawa, Y Yamaguti, K |
| description | Irradiation of organic sulfinates such as hypotaurine and cysteine sulfinic acid in the presence of catalytic amounts of flavins led to the oxidation of its sulfinic groups (-SO2H) to the corresponding sulfonates. The process of hypotaurine oxidation in the presence of riboflavin, followed by absorbance decrease at 220 nm and by ion-exchange chromatography, showed a pseudo-first-order kinetics at pH 6.0. The k value depended linearly on flavin concentrations. The reaction rate was higher at acidic pH. Although the reaction rate was not affected by the addition of superoxide dismutase or catalase, superoxide ions were supposed to be by-products of the reaction. The effectiveness of allyl alcohol as a scavenger pointed to a free-radical mechanism of the reaction. We propose a new reaction mechanism involving sulfinic radicals on this photochemical reaction. |
| doi_str_mv | 10.3177/jnsv.35.143 |
| format | Article |
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(University G. D'Annuzio, Chieti (Italy)) ; Chiaraluce, R ; Pitari, G ; Dupre, S ; Fujii, O ; Hosokawa, Y ; Yamaguti, K</creator><creatorcontrib>Ricci, G. (University G. D'Annuzio, Chieti (Italy)) ; Chiaraluce, R ; Pitari, G ; Dupre, S ; Fujii, O ; Hosokawa, Y ; Yamaguti, K</creatorcontrib><description>Irradiation of organic sulfinates such as hypotaurine and cysteine sulfinic acid in the presence of catalytic amounts of flavins led to the oxidation of its sulfinic groups (-SO2H) to the corresponding sulfonates. The process of hypotaurine oxidation in the presence of riboflavin, followed by absorbance decrease at 220 nm and by ion-exchange chromatography, showed a pseudo-first-order kinetics at pH 6.0. The k value depended linearly on flavin concentrations. The reaction rate was higher at acidic pH. Although the reaction rate was not affected by the addition of superoxide dismutase or catalase, superoxide ions were supposed to be by-products of the reaction. The effectiveness of allyl alcohol as a scavenger pointed to a free-radical mechanism of the reaction. We propose a new reaction mechanism involving sulfinic radicals on this photochemical reaction.</description><identifier>ISSN: 0301-4800</identifier><identifier>EISSN: 1881-7742</identifier><identifier>DOI: 10.3177/jnsv.35.143</identifier><identifier>PMID: 2732808</identifier><language>eng</language><publisher>Japan: Center for Academic Publications Japan</publisher><subject>Amino Acids - analysis ; Catalase - pharmacology ; cysteine sulfinic acid ; flavin ; FLAVINA ; FLAVINE ; FLAVINES ; Flavins ; Hydrogen-Ion Concentration ; hypotaurine ; Kinetics ; LIGHT ; LUMIERE ; LUZ ; OXIDACION ; OXIDATION ; Oxidation-Reduction ; OXYDATION ; Photochemistry ; photooxidation ; Superoxide Dismutase - pharmacology ; TAURINA ; TAURINE ; Taurine - analogs & derivatives ; Ultraviolet Rays</subject><ispartof>Journal of Nutritional Science and Vitaminology, 1989, Vol.35(2), pp.143-153</ispartof><rights>the Center for Academic Publications Japan</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c524t-4cb6b22529b7804e25c88af3663a52bc1c8dcf2459ca723d3ebd81a92025e1323</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,1884,27929,27930</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2732808$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ricci, G. (University G. D'Annuzio, Chieti (Italy))</creatorcontrib><creatorcontrib>Chiaraluce, R</creatorcontrib><creatorcontrib>Pitari, G</creatorcontrib><creatorcontrib>Dupre, S</creatorcontrib><creatorcontrib>Fujii, O</creatorcontrib><creatorcontrib>Hosokawa, Y</creatorcontrib><creatorcontrib>Yamaguti, K</creatorcontrib><title>Photooxidation of hypotaurine taurine in the presence of flavins</title><title>Journal of Nutritional Science and Vitaminology</title><addtitle>J Nutr Sci Vitaminol</addtitle><description>Irradiation of organic sulfinates such as hypotaurine and cysteine sulfinic acid in the presence of catalytic amounts of flavins led to the oxidation of its sulfinic groups (-SO2H) to the corresponding sulfonates. The process of hypotaurine oxidation in the presence of riboflavin, followed by absorbance decrease at 220 nm and by ion-exchange chromatography, showed a pseudo-first-order kinetics at pH 6.0. The k value depended linearly on flavin concentrations. The reaction rate was higher at acidic pH. Although the reaction rate was not affected by the addition of superoxide dismutase or catalase, superoxide ions were supposed to be by-products of the reaction. The effectiveness of allyl alcohol as a scavenger pointed to a free-radical mechanism of the reaction. We propose a new reaction mechanism involving sulfinic radicals on this photochemical reaction.</description><subject>Amino Acids - analysis</subject><subject>Catalase - pharmacology</subject><subject>cysteine sulfinic acid</subject><subject>flavin</subject><subject>FLAVINA</subject><subject>FLAVINE</subject><subject>FLAVINES</subject><subject>Flavins</subject><subject>Hydrogen-Ion Concentration</subject><subject>hypotaurine</subject><subject>Kinetics</subject><subject>LIGHT</subject><subject>LUMIERE</subject><subject>LUZ</subject><subject>OXIDACION</subject><subject>OXIDATION</subject><subject>Oxidation-Reduction</subject><subject>OXYDATION</subject><subject>Photochemistry</subject><subject>photooxidation</subject><subject>Superoxide Dismutase - pharmacology</subject><subject>TAURINA</subject><subject>TAURINE</subject><subject>Taurine - analogs & derivatives</subject><subject>Ultraviolet Rays</subject><issn>0301-4800</issn><issn>1881-7742</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kDtPwzAUhS0EKqUwsSEhZWJBKX4ldjZQeasSHWC2HOemdZXGxU4q-u9JSelyz3C--w0HoUuCx4wIcbesw2bMkjHh7AgNiZQkFoLTYzTEDJOYS4xP0VkIS4x5JrkcoAEVjEosh-h-tnCNcz-20I11deTKaLFdu0a33tYQ_aeto2YB0dpDgNrADisrvbF1OEcnpa4CXOxzhL6enz4nr_H04-Vt8jCNTUJ5E3OTpzmlCc1yITEHmhgpdcnSlOmE5oYYWZiS8iQzWlBWMMgLSXRGMU2AMMpG6Kb3rr37biE0amWDgarSNbg2KJHh7pukHXjbg8a7EDyUau3tSvutIljt9lK7vRRLVLdXR1_vtW2-guLA7gfq-se-X4ZGz-HQa99YU8Gfi2SC7Xy0P532UJuF9grqTnPVa0rtlJ57G9T7LOOYYJayX-gehtE</recordid><startdate>19890101</startdate><enddate>19890101</enddate><creator>Ricci, G. (University G. D'Annuzio, Chieti (Italy))</creator><creator>Chiaraluce, R</creator><creator>Pitari, G</creator><creator>Dupre, S</creator><creator>Fujii, O</creator><creator>Hosokawa, Y</creator><creator>Yamaguti, K</creator><general>Center for Academic Publications Japan</general><scope>FBQ</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>19890101</creationdate><title>Photooxidation of hypotaurine taurine in the presence of flavins</title><author>Ricci, G. (University G. 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(University G. D'Annuzio, Chieti (Italy))</creatorcontrib><creatorcontrib>Chiaraluce, R</creatorcontrib><creatorcontrib>Pitari, G</creatorcontrib><creatorcontrib>Dupre, S</creatorcontrib><creatorcontrib>Fujii, O</creatorcontrib><creatorcontrib>Hosokawa, Y</creatorcontrib><creatorcontrib>Yamaguti, K</creatorcontrib><collection>AGRIS</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>Journal of Nutritional Science and Vitaminology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ricci, G. (University G. 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| ispartof | Journal of Nutritional Science and Vitaminology, 1989, Vol.35(2), pp.143-153 |
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| language | eng |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese |
| subjects | Amino Acids - analysis Catalase - pharmacology cysteine sulfinic acid flavin FLAVINA FLAVINE FLAVINES Flavins Hydrogen-Ion Concentration hypotaurine Kinetics LIGHT LUMIERE LUZ OXIDACION OXIDATION Oxidation-Reduction OXYDATION Photochemistry photooxidation Superoxide Dismutase - pharmacology TAURINA TAURINE Taurine - analogs & derivatives Ultraviolet Rays |
| title | Photooxidation of hypotaurine taurine in the presence of flavins |
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