4-(Dimethylamino)pyridine N-oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2-Methyl-6-nitrobenzoic Anhydride
Various carboxamides or peptides were synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of 4‐(dimethylamino)pyridine N‐oxide (DMAPO) with 2‐methyl‐6‐nitrobenzoic anhydride (MNBA). Because the segment‐coupling reaction of α‐amino acids pro...
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| Veröffentlicht in: | Chemistry, an Asian journal an Asian journal, 2008-02, Vol.3 (2), p.454-461 |
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| creator | Shiina, Isamu Ushiyama, Hisaya Yamada, Yo-ko Kawakita, Yo-ichi Nakata, Kenya |
| description | Various carboxamides or peptides were synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of 4‐(dimethylamino)pyridine N‐oxide (DMAPO) with 2‐methyl‐6‐nitrobenzoic anhydride (MNBA). Because the segment‐coupling reaction of α‐amino acids proceeds through the effective activation of the carboxylic acid moieties with DMAPO in the presence of tertiary amines under mild conditions, undesired racemization was hardly observed in the synthesis of oligopeptides such as Z‐Gly‐Phe‐Val‐OMe, Z‐Phe‐Val‐Ala‐OMe, and Bz‐Val‐Val‐OMe.
An ideal couple: Various carboxamides or peptides can be synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of DMAPO with MNBA. The effective activation of the carboxylic acid moieties in this reaction avoids undesired racemization of the products. |
| doi_str_mv | 10.1002/asia.200700305 |
| format | Article |
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An ideal couple: Various carboxamides or peptides can be synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of DMAPO with MNBA. The effective activation of the carboxylic acid moieties in this reaction avoids undesired racemization of the products.</description><identifier>ISSN: 1861-4728</identifier><identifier>EISSN: 1861-471X</identifier><identifier>DOI: 10.1002/asia.200700305</identifier><identifier>PMID: 18219641</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Anhydrides - chemistry ; carboxamides ; Catalysis ; Cyclic N-Oxides - chemistry ; Molecular Structure ; Nitrobenzoates - chemistry ; oligopeptides ; Oxides - chemical synthesis ; Oxides - chemistry ; peptide coupling ; peptides ; Peptides - chemistry ; synthetic methods</subject><ispartof>Chemistry, an Asian journal, 2008-02, Vol.3 (2), p.454-461</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3815-3be5f167eb114bd1b174f7ccdf152c60dcb61e9ac590c7b140fca88d056f2fd3</citedby><cites>FETCH-LOGICAL-c3815-3be5f167eb114bd1b174f7ccdf152c60dcb61e9ac590c7b140fca88d056f2fd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fasia.200700305$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fasia.200700305$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18219641$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shiina, Isamu</creatorcontrib><creatorcontrib>Ushiyama, Hisaya</creatorcontrib><creatorcontrib>Yamada, Yo-ko</creatorcontrib><creatorcontrib>Kawakita, Yo-ichi</creatorcontrib><creatorcontrib>Nakata, Kenya</creatorcontrib><title>4-(Dimethylamino)pyridine N-oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2-Methyl-6-nitrobenzoic Anhydride</title><title>Chemistry, an Asian journal</title><addtitle>Chemistry - An Asian Journal</addtitle><description>Various carboxamides or peptides were synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of 4‐(dimethylamino)pyridine N‐oxide (DMAPO) with 2‐methyl‐6‐nitrobenzoic anhydride (MNBA). Because the segment‐coupling reaction of α‐amino acids proceeds through the effective activation of the carboxylic acid moieties with DMAPO in the presence of tertiary amines under mild conditions, undesired racemization was hardly observed in the synthesis of oligopeptides such as Z‐Gly‐Phe‐Val‐OMe, Z‐Phe‐Val‐Ala‐OMe, and Bz‐Val‐Val‐OMe.
An ideal couple: Various carboxamides or peptides can be synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of DMAPO with MNBA. The effective activation of the carboxylic acid moieties in this reaction avoids undesired racemization of the products.</description><subject>Anhydrides - chemistry</subject><subject>carboxamides</subject><subject>Catalysis</subject><subject>Cyclic N-Oxides - chemistry</subject><subject>Molecular Structure</subject><subject>Nitrobenzoates - chemistry</subject><subject>oligopeptides</subject><subject>Oxides - chemical synthesis</subject><subject>Oxides - chemistry</subject><subject>peptide coupling</subject><subject>peptides</subject><subject>Peptides - chemistry</subject><subject>synthetic methods</subject><issn>1861-4728</issn><issn>1861-471X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1u1DAUhSMEoqWwZYm8Qu3Cg-0kTsIuTH-o6C-MBDvLca6JIbFD7LQN78H7kmFGAztW19L9vnMlnyh6ScmCEsLeSG_kghGSERKT9FG0T3NOcZLRL493b5bvRc-8_0ZIykiRP432aM5owRO6H_1K8OGx6SA0Uys7Y91RPw2mNhbQFXYPpgZ0eHxZ3lwfvUWlRSdagwrmbt6OqgXXN6Y1Ci1lkO3kAzIWhQbQDfRhrS7d2LfGfkUfQc6as-jehAYxfPnnIObYmjC4CuxPN8eUtpnq-To8j55o2Xp4sZ0H0er0ZLV8jy-uz86X5QVWcU5THFeQasozqChNqppWNEt0plStacoUJ7WqOIVCqrQgKqtoQrSSeV6TlGum6_gger2J7Qf3YwQfRGe8graVFtzoRUYYj-OEz-BiA6rBeT-AFv1gOjlMghKx7kGsexC7Hmbh1TZ5rDqo_-Lbj5-BYgPcmxam_8SJ8tN5-W843rjGB3jYuXL4LngWZ6n4fHUmbovVB8bid-I2_g2NeKUv</recordid><startdate>20080201</startdate><enddate>20080201</enddate><creator>Shiina, Isamu</creator><creator>Ushiyama, Hisaya</creator><creator>Yamada, Yo-ko</creator><creator>Kawakita, Yo-ichi</creator><creator>Nakata, Kenya</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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>20080201</creationdate><title>4-(Dimethylamino)pyridine N-oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2-Methyl-6-nitrobenzoic Anhydride</title><author>Shiina, Isamu ; Ushiyama, Hisaya ; Yamada, Yo-ko ; Kawakita, Yo-ichi ; Nakata, Kenya</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3815-3be5f167eb114bd1b174f7ccdf152c60dcb61e9ac590c7b140fca88d056f2fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Anhydrides - chemistry</topic><topic>carboxamides</topic><topic>Catalysis</topic><topic>Cyclic N-Oxides - chemistry</topic><topic>Molecular Structure</topic><topic>Nitrobenzoates - chemistry</topic><topic>oligopeptides</topic><topic>Oxides - chemical synthesis</topic><topic>Oxides - chemistry</topic><topic>peptide coupling</topic><topic>peptides</topic><topic>Peptides - chemistry</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shiina, Isamu</creatorcontrib><creatorcontrib>Ushiyama, Hisaya</creatorcontrib><creatorcontrib>Yamada, Yo-ko</creatorcontrib><creatorcontrib>Kawakita, Yo-ichi</creatorcontrib><creatorcontrib>Nakata, Kenya</creatorcontrib><collection>Istex</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>Chemistry, an Asian journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shiina, Isamu</au><au>Ushiyama, Hisaya</au><au>Yamada, Yo-ko</au><au>Kawakita, Yo-ichi</au><au>Nakata, Kenya</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>4-(Dimethylamino)pyridine N-oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2-Methyl-6-nitrobenzoic Anhydride</atitle><jtitle>Chemistry, an Asian journal</jtitle><addtitle>Chemistry - An Asian Journal</addtitle><date>2008-02-01</date><risdate>2008</risdate><volume>3</volume><issue>2</issue><spage>454</spage><epage>461</epage><pages>454-461</pages><issn>1861-4728</issn><eissn>1861-471X</eissn><abstract>Various carboxamides or peptides were synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of 4‐(dimethylamino)pyridine N‐oxide (DMAPO) with 2‐methyl‐6‐nitrobenzoic anhydride (MNBA). Because the segment‐coupling reaction of α‐amino acids proceeds through the effective activation of the carboxylic acid moieties with DMAPO in the presence of tertiary amines under mild conditions, undesired racemization was hardly observed in the synthesis of oligopeptides such as Z‐Gly‐Phe‐Val‐OMe, Z‐Phe‐Val‐Ala‐OMe, and Bz‐Val‐Val‐OMe.
An ideal couple: Various carboxamides or peptides can be synthesized from the corresponding carboxylic acids and amines or α‐amino acids in high yields by the catalysis of DMAPO with MNBA. The effective activation of the carboxylic acid moieties in this reaction avoids undesired racemization of the products.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>18219641</pmid><doi>10.1002/asia.200700305</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 1861-4728 |
| ispartof | Chemistry, an Asian journal, 2008-02, Vol.3 (2), p.454-461 |
| issn | 1861-4728 1861-471X |
| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals; MEDLINE |
| subjects | Anhydrides - chemistry carboxamides Catalysis Cyclic N-Oxides - chemistry Molecular Structure Nitrobenzoates - chemistry oligopeptides Oxides - chemical synthesis Oxides - chemistry peptide coupling peptides Peptides - chemistry synthetic methods |
| title | 4-(Dimethylamino)pyridine N-oxide (DMAPO): An Effective Nucleophilic Catalyst in the Peptide Coupling Reaction with 2-Methyl-6-nitrobenzoic Anhydride |
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