Periodate Oxidation of Pseudouridine 5'-Phosphate and Spectral Characterization of the Products
Under the conditions for oxidative degradation, with a 2-fold molar excess of periodate and cyclohexylamine at room temperature, ÏMP is degraded to inorganic phosphate but fails to release the base. In this latter respect, the parent pseudouridine behaves similarly. Under more drastic conditions, w...
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| Veröffentlicht in: | The Journal of biological chemistry 1969-05, Vol.244 (10), p.2750-2754 |
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| container_title | The Journal of biological chemistry |
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| creator | Dugaiczyk, A Eiler, J J |
| description | Under the conditions for oxidative degradation, with a 2-fold molar excess of periodate and cyclohexylamine at room temperature,
ÏMP is degraded to inorganic phosphate but fails to release the base. In this latter respect, the parent pseudouridine behaves
similarly. Under more drastic conditions, with a prolonged treatment at 45° and a 6-fold molar excess of periodate and cyclohexylamine,
ÏMP is degraded to inorganic phosphate and a mixture of 5-formyluracil and 5-carboxyuracil.
The apparent pK a values of 5-formyluracil, calculated from ultraviolet absorption spectra at various pH values, are 6.8 and >11.2. The
same constants of 5-carboxyuracil are 4.3,9.15, and >13.2. Analysis of the spectral data shows that in both of these 5-substituted
uracil derivatives anion formation involves loss of a proton from N-1 rather than from N-3 of the uracil ring. |
| doi_str_mv | 10.1016/S0021-9258(18)83459-7 |
| format | Article |
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ÏMP is degraded to inorganic phosphate but fails to release the base. In this latter respect, the parent pseudouridine behaves
similarly. Under more drastic conditions, with a prolonged treatment at 45° and a 6-fold molar excess of periodate and cyclohexylamine,
ÏMP is degraded to inorganic phosphate and a mixture of 5-formyluracil and 5-carboxyuracil.
The apparent pK a values of 5-formyluracil, calculated from ultraviolet absorption spectra at various pH values, are 6.8 and >11.2. The
same constants of 5-carboxyuracil are 4.3,9.15, and >13.2. Analysis of the spectral data shows that in both of these 5-substituted
uracil derivatives anion formation involves loss of a proton from N-1 rather than from N-3 of the uracil ring.</description><identifier>ISSN: 0021-9258</identifier><identifier>EISSN: 1083-351X</identifier><identifier>DOI: 10.1016/S0021-9258(18)83459-7</identifier><identifier>PMID: 4306036</identifier><language>eng</language><publisher>United States: American Society for Biochemistry and Molecular Biology</publisher><subject>Amines ; Chemical Phenomena ; Chemistry ; Hydrogen-Ion Concentration ; Nucleotides ; Periodic Acid ; Solutions ; Spectrophotometry ; Ultraviolet Rays ; Uracil</subject><ispartof>The Journal of biological chemistry, 1969-05, Vol.244 (10), p.2750-2754</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c379t-1518aae3d2a7224781bb20f91237f7f63fe7dd32614f1e216662e7c87e237da23</citedby><cites>FETCH-LOGICAL-c379t-1518aae3d2a7224781bb20f91237f7f63fe7dd32614f1e216662e7c87e237da23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/4306036$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dugaiczyk, A</creatorcontrib><creatorcontrib>Eiler, J J</creatorcontrib><title>Periodate Oxidation of Pseudouridine 5'-Phosphate and Spectral Characterization of the Products</title><title>The Journal of biological chemistry</title><addtitle>J Biol Chem</addtitle><description>Under the conditions for oxidative degradation, with a 2-fold molar excess of periodate and cyclohexylamine at room temperature,
ÏMP is degraded to inorganic phosphate but fails to release the base. In this latter respect, the parent pseudouridine behaves
similarly. Under more drastic conditions, with a prolonged treatment at 45° and a 6-fold molar excess of periodate and cyclohexylamine,
ÏMP is degraded to inorganic phosphate and a mixture of 5-formyluracil and 5-carboxyuracil.
The apparent pK a values of 5-formyluracil, calculated from ultraviolet absorption spectra at various pH values, are 6.8 and >11.2. The
same constants of 5-carboxyuracil are 4.3,9.15, and >13.2. Analysis of the spectral data shows that in both of these 5-substituted
uracil derivatives anion formation involves loss of a proton from N-1 rather than from N-3 of the uracil ring.</description><subject>Amines</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Nucleotides</subject><subject>Periodic Acid</subject><subject>Solutions</subject><subject>Spectrophotometry</subject><subject>Ultraviolet Rays</subject><subject>Uracil</subject><issn>0021-9258</issn><issn>1083-351X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1969</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kNtKAzEQhoMotVYfQVgQPFysZpLsJnspxRMUWqiCdyHdzLqRtqnJLh6e3u2Bzs1czPf_Ax8h50BvgUJ-N6WUQVqwTF2DulFcZEUqD0gfqOIpz-D9kPT3yDE5ifGTdiMK6JGe4DSnPO8TPcHgvDUNJuMf123nl4mvkknE1vo2OOuWmGRX6aT2cVWvObO0yXSFZRPMPBnWJpiy6Ur-9tmmxmQSvG3LJp6So8rMI57t9oC8PT68Dp_T0fjpZXg_SksuiyaFDJQxyC0zkjEhFcxmjFYFMC4rWeW8QmktZzmICpBBnucMZakkdoA1jA_I5bZ3FfxXi7HRCxdLnM_NEn0btRIgMlaoDsy2YBl8jAErvQpuYcKvBqrXYvVGrF5b06D0RqyWXe5896CdLdDuUzuT3f1ie6_dR_3tAuqZ82WNC82EWHczmVH-D-X-f1o</recordid><startdate>19690525</startdate><enddate>19690525</enddate><creator>Dugaiczyk, A</creator><creator>Eiler, J J</creator><general>American Society for Biochemistry and Molecular Biology</general><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>19690525</creationdate><title>Periodate Oxidation of Pseudouridine 5'-Phosphate and Spectral Characterization of the Products</title><author>Dugaiczyk, A ; Eiler, J J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c379t-1518aae3d2a7224781bb20f91237f7f63fe7dd32614f1e216662e7c87e237da23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1969</creationdate><topic>Amines</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Nucleotides</topic><topic>Periodic Acid</topic><topic>Solutions</topic><topic>Spectrophotometry</topic><topic>Ultraviolet Rays</topic><topic>Uracil</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dugaiczyk, A</creatorcontrib><creatorcontrib>Eiler, J J</creatorcontrib><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>The Journal of biological chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dugaiczyk, A</au><au>Eiler, J J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Periodate Oxidation of Pseudouridine 5'-Phosphate and Spectral Characterization of the Products</atitle><jtitle>The Journal of biological chemistry</jtitle><addtitle>J Biol Chem</addtitle><date>1969-05-25</date><risdate>1969</risdate><volume>244</volume><issue>10</issue><spage>2750</spage><epage>2754</epage><pages>2750-2754</pages><issn>0021-9258</issn><eissn>1083-351X</eissn><abstract>Under the conditions for oxidative degradation, with a 2-fold molar excess of periodate and cyclohexylamine at room temperature,
ÏMP is degraded to inorganic phosphate but fails to release the base. In this latter respect, the parent pseudouridine behaves
similarly. Under more drastic conditions, with a prolonged treatment at 45° and a 6-fold molar excess of periodate and cyclohexylamine,
ÏMP is degraded to inorganic phosphate and a mixture of 5-formyluracil and 5-carboxyuracil.
The apparent pK a values of 5-formyluracil, calculated from ultraviolet absorption spectra at various pH values, are 6.8 and >11.2. The
same constants of 5-carboxyuracil are 4.3,9.15, and >13.2. Analysis of the spectral data shows that in both of these 5-substituted
uracil derivatives anion formation involves loss of a proton from N-1 rather than from N-3 of the uracil ring.</abstract><cop>United States</cop><pub>American Society for Biochemistry and Molecular Biology</pub><pmid>4306036</pmid><doi>10.1016/S0021-9258(18)83459-7</doi><tpages>5</tpages><oa>free_for_read</oa></addata></record> |
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| ispartof | The Journal of biological chemistry, 1969-05, Vol.244 (10), p.2750-2754 |
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| language | eng |
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| source | MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Alma/SFX Local Collection |
| subjects | Amines Chemical Phenomena Chemistry Hydrogen-Ion Concentration Nucleotides Periodic Acid Solutions Spectrophotometry Ultraviolet Rays Uracil |
| title | Periodate Oxidation of Pseudouridine 5'-Phosphate and Spectral Characterization of the Products |
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