Synthesis and Characterization of "Picnic-Basket" Porphyrins with a Substituent in the Interior of the Pocket
"Picnic-basket" porphyrins of a new type, that have a substituent in the interior of the pocket, were synthesized to study stabilization of the bound oxygen in hemoprotein models. Though these Co(II) porphyrins have enormous equilibrium constants for the formation of base adducts, hydrogen...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1992/12/25, Vol.40(12), pp.3157-3162 |
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| container_issue | 12 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 40 |
| creator | MICHIDA, Takashi KYUHARA, Masahiro NISHIYAMA, Michiko YOSHIMI, Yukihiro FITZGERALD, Jeffrey P. SAYO, Hiroteru |
| description | "Picnic-basket" porphyrins of a new type, that have a substituent in the interior of the pocket, were synthesized to study stabilization of the bound oxygen in hemoprotein models. Though these Co(II) porphyrins have enormous equilibrium constants for the formation of base adducts, hydrogen-bonding interaction with coordinated dioxygen is not as effective for stabilization of the metal-dioxygen bond as we had expected. The results suggest that doming of the porphyrin plane plays an important role in the binding of dioxygen. |
| doi_str_mv | 10.1248/cpb.40.3157 |
| format | Article |
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Though these Co(II) porphyrins have enormous equilibrium constants for the formation of base adducts, hydrogen-bonding interaction with coordinated dioxygen is not as effective for stabilization of the metal-dioxygen bond as we had expected. 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Pharm. Bull.</addtitle><description>"Picnic-basket" porphyrins of a new type, that have a substituent in the interior of the pocket, were synthesized to study stabilization of the bound oxygen in hemoprotein models. Though these Co(II) porphyrins have enormous equilibrium constants for the formation of base adducts, hydrogen-bonding interaction with coordinated dioxygen is not as effective for stabilization of the metal-dioxygen bond as we had expected. The results suggest that doming of the porphyrin plane plays an important role in the binding of dioxygen.</description><subject>base-binding</subject><subject>Chemistry</subject><subject>cobalt porphyrin</subject><subject>dioxygen carrier</subject><subject>ESR</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>hydrogen-bonding</subject><subject>Organic chemistry</subject><subject>porphyrin</subject><subject>Preparations and properties</subject><subject>synthesis</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><recordid>eNpFkcFuGyEQhlHVSnWTnPoCKO0tWgcYdlkfUytpIkWKpTRnNGahxnVYB7Ai5-kLspVcGCG--Ub8Q8h3zqZcyP7SbJdTyabAW_WJTDhI1bRCwGcyYYzNGgEdfCXfUlozJlqmYEKeH_chr2zyiWIY6HyFEU220b9h9mOgo6PnC2-CN80vTP9sPqeLMW5X--hDoq8-ryjSx90yZZ93NmTqAy0-eheqZIxVUO-L0ZTmU_LF4SbZs2M9IU8313_mt839w--7-dV9Y2QPuYFOOkBloB_QSpy1feu4msm2Xw7AwKEZOmDOOKaEgZbbJR-EFArEYBnjACfkx8G7jePLzqas1-MuhjJSc9kx0XWy54W6OFAmjilF6_Q2-meMe82ZrnnqkqeWTNc8C_3z6MRkcOMiBuPTe4tUJWJVR98csHXK-Ne-v2PM3mxsVfLyoarl4nhW_wdQVqBtgP9Oro2Q</recordid><startdate>1992</startdate><enddate>1992</enddate><creator>MICHIDA, Takashi</creator><creator>KYUHARA, Masahiro</creator><creator>NISHIYAMA, Michiko</creator><creator>YOSHIMI, Yukihiro</creator><creator>FITZGERALD, Jeffrey P.</creator><creator>SAYO, Hiroteru</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><general>Japan Science and Technology Agency</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>1992</creationdate><title>Synthesis and Characterization of "Picnic-Basket" Porphyrins with a Substituent in the Interior of the Pocket</title><author>MICHIDA, Takashi ; KYUHARA, Masahiro ; NISHIYAMA, Michiko ; YOSHIMI, Yukihiro ; FITZGERALD, Jeffrey P. ; SAYO, Hiroteru</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c483t-364f3a7c38dae4a9585f179458bd303facd630fcf072c351eb1d242732de00133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1992</creationdate><topic>base-binding</topic><topic>Chemistry</topic><topic>cobalt porphyrin</topic><topic>dioxygen carrier</topic><topic>ESR</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>hydrogen-bonding</topic><topic>Organic chemistry</topic><topic>porphyrin</topic><topic>Preparations and properties</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>MICHIDA, Takashi</creatorcontrib><creatorcontrib>KYUHARA, Masahiro</creatorcontrib><creatorcontrib>NISHIYAMA, Michiko</creatorcontrib><creatorcontrib>YOSHIMI, Yukihiro</creatorcontrib><creatorcontrib>FITZGERALD, Jeffrey P.</creatorcontrib><creatorcontrib>SAYO, Hiroteru</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>MICHIDA, Takashi</au><au>KYUHARA, Masahiro</au><au>NISHIYAMA, Michiko</au><au>YOSHIMI, Yukihiro</au><au>FITZGERALD, Jeffrey P.</au><au>SAYO, Hiroteru</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of "Picnic-Basket" Porphyrins with a Substituent in the Interior of the Pocket</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1992</date><risdate>1992</risdate><volume>40</volume><issue>12</issue><spage>3157</spage><epage>3162</epage><pages>3157-3162</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>"Picnic-basket" porphyrins of a new type, that have a substituent in the interior of the pocket, were synthesized to study stabilization of the bound oxygen in hemoprotein models. Though these Co(II) porphyrins have enormous equilibrium constants for the formation of base adducts, hydrogen-bonding interaction with coordinated dioxygen is not as effective for stabilization of the metal-dioxygen bond as we had expected. The results suggest that doming of the porphyrin plane plays an important role in the binding of dioxygen.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.40.3157</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1992/12/25, Vol.40(12), pp.3157-3162 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_journals_1460266481 |
| source | J-STAGE Free; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | base-binding Chemistry cobalt porphyrin dioxygen carrier ESR Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms hydrogen-bonding Organic chemistry porphyrin Preparations and properties synthesis |
| title | Synthesis and Characterization of "Picnic-Basket" Porphyrins with a Substituent in the Interior of the Pocket |
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