THE STRUCTURES OF THE m-CHLOROPERBENZOIC ACID OXIDATION PRODUCTS OF 8, 9-ANHYDROERYTHROMYCINS A-AND B-6, 9-HEMIACETAL AND OF (8S)-8-HYDROXYERYTHROMYCIN B
13C-NMR studies have confirmed the structures of (8S)-8-hydroxyerythromycins A- and B-6, 9;9, 11-acetal proposed by KROWICKI and ZAMOJSKI2, 3) for the products of the m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycins A- and B-6, 9-hemiacetal. The preparations of (8S)-8-methylthiomethoxy...
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| Veröffentlicht in: | Journal of antibiotics 1978, Vol.31(1), pp.55-62 |
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| creator | EGAN, RICHARD S. MARTIN, JERRY R. MCALPINE, JAMES B. KURATH, PAUL STANASZEK, RUTH S. GOLDSTEIN, ALMA W. JOHNSON, LEROY F. |
| description | 13C-NMR studies have confirmed the structures of (8S)-8-hydroxyerythromycins A- and B-6, 9;9, 11-acetal proposed by KROWICKI and ZAMOJSKI2, 3) for the products of the m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycins A- and B-6, 9-hemiacetal. The preparations of (8S)-8-methylthiomethoxy- and (8S)-8-methoxyerythromycin B-6, 9;9, 11-acetals are described. The latter are stable in aqueous acetic acid under conditions which convert (8S)-8-hydroxyerythromycin B-6, 9;9, 11-acetalinto (8S)-8-hydroxyerythromycin B. In a paper describing the preparation of the C8-epimeric 8-hydroxyerythromycins B, we reported1) that buffered m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycin B-6, 9-hemiacetal (1), followed by catalytic reduction of the resulting N-oxide to the free amine, gave (8S, 9S)-8, 9-anhydroerythromycin B-6, 9-hemiacetal-8, 9-epoxide (2). Our assignment of structure 2 was based on the expected course of olefin epoxidation with peracids and with apparently compatible spectral properties. In addition, the facile conversion of 2 to (8S)-8-hydroxyerythromycin B (3) in aqueous acetic acid was expected for the strained epoxy spiroacetal structure (2). |
| doi_str_mv | 10.7164/antibiotics.31.55 |
| format | Article |
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The preparations of (8S)-8-methylthiomethoxy- and (8S)-8-methoxyerythromycin B-6, 9;9, 11-acetals are described. The latter are stable in aqueous acetic acid under conditions which convert (8S)-8-hydroxyerythromycin B-6, 9;9, 11-acetalinto (8S)-8-hydroxyerythromycin B. In a paper describing the preparation of the C8-epimeric 8-hydroxyerythromycins B, we reported1) that buffered m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycin B-6, 9-hemiacetal (1), followed by catalytic reduction of the resulting N-oxide to the free amine, gave (8S, 9S)-8, 9-anhydroerythromycin B-6, 9-hemiacetal-8, 9-epoxide (2). Our assignment of structure 2 was based on the expected course of olefin epoxidation with peracids and with apparently compatible spectral properties. In addition, the facile conversion of 2 to (8S)-8-hydroxyerythromycin B (3) in aqueous acetic acid was expected for the strained epoxy spiroacetal structure (2).</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.7164/antibiotics.31.55</identifier><identifier>PMID: 627523</identifier><language>eng</language><publisher>Japan: JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</publisher><subject>Acetates ; Chemical Phenomena ; Chemistry ; Chlorobenzoates ; Drug Stability ; Erythromycin - analogs & derivatives ; Methods ; Oxidation-Reduction ; Peroxides</subject><ispartof>The Journal of Antibiotics, 1978, Vol.31(1), pp.55-62</ispartof><rights>Japan Antibiotics Research Association</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4875-5660ff79a72456cb817deb4e039502b853643d7c83011f584e6c2594f66de5223</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,4010,27900,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/627523$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>EGAN, RICHARD S.</creatorcontrib><creatorcontrib>MARTIN, JERRY R.</creatorcontrib><creatorcontrib>MCALPINE, JAMES B.</creatorcontrib><creatorcontrib>KURATH, PAUL</creatorcontrib><creatorcontrib>STANASZEK, RUTH S.</creatorcontrib><creatorcontrib>GOLDSTEIN, ALMA W.</creatorcontrib><creatorcontrib>JOHNSON, LEROY F.</creatorcontrib><title>THE STRUCTURES OF THE m-CHLOROPERBENZOIC ACID OXIDATION PRODUCTS OF 8, 9-ANHYDROERYTHROMYCINS A-AND B-6, 9-HEMIACETAL AND OF (8S)-8-HYDROXYERYTHROMYCIN B</title><title>Journal of antibiotics</title><addtitle>J. Antibiot.</addtitle><description>13C-NMR studies have confirmed the structures of (8S)-8-hydroxyerythromycins A- and B-6, 9;9, 11-acetal proposed by KROWICKI and ZAMOJSKI2, 3) for the products of the m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycins A- and B-6, 9-hemiacetal. The preparations of (8S)-8-methylthiomethoxy- and (8S)-8-methoxyerythromycin B-6, 9;9, 11-acetals are described. The latter are stable in aqueous acetic acid under conditions which convert (8S)-8-hydroxyerythromycin B-6, 9;9, 11-acetalinto (8S)-8-hydroxyerythromycin B. In a paper describing the preparation of the C8-epimeric 8-hydroxyerythromycins B, we reported1) that buffered m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycin B-6, 9-hemiacetal (1), followed by catalytic reduction of the resulting N-oxide to the free amine, gave (8S, 9S)-8, 9-anhydroerythromycin B-6, 9-hemiacetal-8, 9-epoxide (2). Our assignment of structure 2 was based on the expected course of olefin epoxidation with peracids and with apparently compatible spectral properties. In addition, the facile conversion of 2 to (8S)-8-hydroxyerythromycin B (3) in aqueous acetic acid was expected for the strained epoxy spiroacetal structure (2).</description><subject>Acetates</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Chlorobenzoates</subject><subject>Drug Stability</subject><subject>Erythromycin - analogs & derivatives</subject><subject>Methods</subject><subject>Oxidation-Reduction</subject><subject>Peroxides</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1978</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpNkUtv00AUhUeIVyj8ACQWs6pAYsK8Z7x0bBcbpZnKcaSGzch2xuAqj-JJFvwU_i12XUXZ3Cudc76zuBeAjwRPFZH8W7k_tlV7OLa1nzIyFeIFmBCtCSJcBi_BBGNKkNYUvwXvvH_AmCmm9BvwWlIlKJuAf0WawGWRr6JilSdLaG7goOxQlM5Nbu6SfJYsfposgmGUxdDcZ3FYZGYB73IT99ATob_CAIWLdB3nJsnXRZqb23WULZYw7OUYzpAcEmlym4VRUoRzOKg9-FkvvyCNnsD79SUKZ-_Bq6bcevfheV-B1U1SRCmam-9ZFM5RzbUSSEiJm0YFpaJcyLrSRG1cxR1mgcC00oJJzjaq1gwT0gjNnaypCHgj5cYJStkVuB57H7vDn5PzR7trfe2223LvDidvNdOYC0r6IBmDdXfwvnONfezaXdn9tQTb4Rv24huWEStEz3x6Lj9VO7c5E-P5e_vHaD_4Y_nLne2y6zu27rKQBFIPpWQcQpxD9e-ys27P_gP6WpYD</recordid><startdate>1978</startdate><enddate>1978</enddate><creator>EGAN, RICHARD S.</creator><creator>MARTIN, JERRY R.</creator><creator>MCALPINE, JAMES B.</creator><creator>KURATH, PAUL</creator><creator>STANASZEK, RUTH S.</creator><creator>GOLDSTEIN, ALMA W.</creator><creator>JOHNSON, LEROY F.</creator><general>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</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>1978</creationdate><title>THE STRUCTURES OF THE m-CHLOROPERBENZOIC ACID OXIDATION PRODUCTS OF 8, 9-ANHYDROERYTHROMYCINS A-AND B-6, 9-HEMIACETAL AND OF (8S)-8-HYDROXYERYTHROMYCIN B</title><author>EGAN, RICHARD S. ; MARTIN, JERRY R. ; MCALPINE, JAMES B. ; KURATH, PAUL ; STANASZEK, RUTH S. ; GOLDSTEIN, ALMA W. ; JOHNSON, LEROY F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4875-5660ff79a72456cb817deb4e039502b853643d7c83011f584e6c2594f66de5223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><topic>Acetates</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Chlorobenzoates</topic><topic>Drug Stability</topic><topic>Erythromycin - analogs & derivatives</topic><topic>Methods</topic><topic>Oxidation-Reduction</topic><topic>Peroxides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>EGAN, RICHARD S.</creatorcontrib><creatorcontrib>MARTIN, JERRY R.</creatorcontrib><creatorcontrib>MCALPINE, JAMES B.</creatorcontrib><creatorcontrib>KURATH, PAUL</creatorcontrib><creatorcontrib>STANASZEK, RUTH S.</creatorcontrib><creatorcontrib>GOLDSTEIN, ALMA W.</creatorcontrib><creatorcontrib>JOHNSON, LEROY F.</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>Journal of antibiotics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>EGAN, RICHARD S.</au><au>MARTIN, JERRY R.</au><au>MCALPINE, JAMES B.</au><au>KURATH, PAUL</au><au>STANASZEK, RUTH S.</au><au>GOLDSTEIN, ALMA W.</au><au>JOHNSON, LEROY F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>THE STRUCTURES OF THE m-CHLOROPERBENZOIC ACID OXIDATION PRODUCTS OF 8, 9-ANHYDROERYTHROMYCINS A-AND B-6, 9-HEMIACETAL AND OF (8S)-8-HYDROXYERYTHROMYCIN B</atitle><jtitle>Journal of antibiotics</jtitle><addtitle>J. Antibiot.</addtitle><date>1978</date><risdate>1978</risdate><volume>31</volume><issue>1</issue><spage>55</spage><epage>62</epage><pages>55-62</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><abstract>13C-NMR studies have confirmed the structures of (8S)-8-hydroxyerythromycins A- and B-6, 9;9, 11-acetal proposed by KROWICKI and ZAMOJSKI2, 3) for the products of the m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycins A- and B-6, 9-hemiacetal. The preparations of (8S)-8-methylthiomethoxy- and (8S)-8-methoxyerythromycin B-6, 9;9, 11-acetals are described. The latter are stable in aqueous acetic acid under conditions which convert (8S)-8-hydroxyerythromycin B-6, 9;9, 11-acetalinto (8S)-8-hydroxyerythromycin B. In a paper describing the preparation of the C8-epimeric 8-hydroxyerythromycins B, we reported1) that buffered m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycin B-6, 9-hemiacetal (1), followed by catalytic reduction of the resulting N-oxide to the free amine, gave (8S, 9S)-8, 9-anhydroerythromycin B-6, 9-hemiacetal-8, 9-epoxide (2). Our assignment of structure 2 was based on the expected course of olefin epoxidation with peracids and with apparently compatible spectral properties. In addition, the facile conversion of 2 to (8S)-8-hydroxyerythromycin B (3) in aqueous acetic acid was expected for the strained epoxy spiroacetal structure (2).</abstract><cop>Japan</cop><pub>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</pub><pmid>627523</pmid><doi>10.7164/antibiotics.31.55</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 0021-8820 |
| ispartof | The Journal of Antibiotics, 1978, Vol.31(1), pp.55-62 |
| issn | 0021-8820 1881-1469 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_83804521 |
| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese |
| subjects | Acetates Chemical Phenomena Chemistry Chlorobenzoates Drug Stability Erythromycin - analogs & derivatives Methods Oxidation-Reduction Peroxides |
| title | THE STRUCTURES OF THE m-CHLOROPERBENZOIC ACID OXIDATION PRODUCTS OF 8, 9-ANHYDROERYTHROMYCINS A-AND B-6, 9-HEMIACETAL AND OF (8S)-8-HYDROXYERYTHROMYCIN B |
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