An efficient method for the synthesis of phenacyl ester-protected dipeptides using neutral alumina-supported sodium carbonate 'Na2CO3/n-Al2O3'
In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐...
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| Veröffentlicht in: | Journal of peptide science 2013-10, Vol.19 (10), p.659-662 |
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| container_title | Journal of peptide science |
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| creator | Hashimoto, Chikao Sugimoto, Kazuhiro Takahashi, Youhei Kodomari, Mitsuo |
| description | In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐AA2‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using amines for the conversion afforded an unsatisfactory yield with by‐products. On the other hand, the use of neutral alumina‐supported Na2CO3 (Na2CO3/n‐Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products. The application of Na2CO3/n‐Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields. Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.
In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐AA2‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using neutral alumina‐supported Na2CO3 (Na2CO3/n‐Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products compared with the synthesis employing amines. The application of Na2CO3/n‐Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields. |
| doi_str_mv | 10.1002/psc.2544 |
| format | Article |
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In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐AA2‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using neutral alumina‐supported Na2CO3 (Na2CO3/n‐Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products compared with the synthesis employing amines. The application of Na2CO3/n‐Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields.</description><identifier>ISSN: 1075-2617</identifier><identifier>EISSN: 1099-1387</identifier><identifier>DOI: 10.1002/psc.2544</identifier><identifier>CODEN: JPSIEI</identifier><language>eng</language><publisher>Bognor Regis: Blackwell Publishing Ltd</publisher><subject>amine ; neutral alumina-supported sodium carbonate ; peptide synthesis ; Peptides ; phenacyl ester ; solid base</subject><ispartof>Journal of peptide science, 2013-10, Vol.19 (10), p.659-662</ispartof><rights>Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpsc.2544$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpsc.2544$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Hashimoto, Chikao</creatorcontrib><creatorcontrib>Sugimoto, Kazuhiro</creatorcontrib><creatorcontrib>Takahashi, Youhei</creatorcontrib><creatorcontrib>Kodomari, Mitsuo</creatorcontrib><title>An efficient method for the synthesis of phenacyl ester-protected dipeptides using neutral alumina-supported sodium carbonate 'Na2CO3/n-Al2O3'</title><title>Journal of peptide science</title><addtitle>J. Pept. Sci</addtitle><description>In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐AA2‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using amines for the conversion afforded an unsatisfactory yield with by‐products. On the other hand, the use of neutral alumina‐supported Na2CO3 (Na2CO3/n‐Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products. The application of Na2CO3/n‐Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields. Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.
In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐AA2‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using neutral alumina‐supported Na2CO3 (Na2CO3/n‐Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products compared with the synthesis employing amines. The application of Na2CO3/n‐Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields.</description><subject>amine</subject><subject>neutral alumina-supported sodium carbonate</subject><subject>peptide synthesis</subject><subject>Peptides</subject><subject>phenacyl ester</subject><subject>solid base</subject><issn>1075-2617</issn><issn>1099-1387</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNpFkF1r2zAUhs3YoFlX6E8Q7KJXavRhSc5lCFs7mjYracmlkO2jRZ0je5JMlz-x31yZjvbqPXAezuF9iuKckktKCJsPsblkoiw_FDNKFgtMeaU-TrMSmEmqTorPMT4RkndCzop_S4_AWtc48AkdIO37Ftk-oLQHFI8-R3QR9RYNe_CmOXYIYoKAh9AnaBK0qHUDDMm1ENEYnf-FPIwpmA6Zbjw4b3Ach6EPExr71o0H1JhQ994kQBd3hq02fO7xsmMbfvGl-GRNF-Hsf54Wj9-_Payu8Xpz9WO1XGPHxKLElVGiAmVYJW3JuKramtdCqpJYq0hNG4BK0opIwerWcJUlyJIZS5raSNVaflp8fb2ba_wZcyP91I_B55ealpwILhUlmcKv1LPr4KiH4A4mHDUlelKts2o9qdY_t6sp33mXFf194034raXiSujd3ZXekZvd9na91ff8BWdRg7I</recordid><startdate>201310</startdate><enddate>201310</enddate><creator>Hashimoto, Chikao</creator><creator>Sugimoto, Kazuhiro</creator><creator>Takahashi, Youhei</creator><creator>Kodomari, Mitsuo</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>7QO</scope><scope>7TK</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>P64</scope></search><sort><creationdate>201310</creationdate><title>An efficient method for the synthesis of phenacyl ester-protected dipeptides using neutral alumina-supported sodium carbonate 'Na2CO3/n-Al2O3'</title><author>Hashimoto, Chikao ; Sugimoto, Kazuhiro ; Takahashi, Youhei ; Kodomari, Mitsuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i2594-8a758e7a286f42378db3b56740ff70b1cee86180652bda37138642af0cba67df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>amine</topic><topic>neutral alumina-supported sodium carbonate</topic><topic>peptide synthesis</topic><topic>Peptides</topic><topic>phenacyl ester</topic><topic>solid base</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hashimoto, Chikao</creatorcontrib><creatorcontrib>Sugimoto, Kazuhiro</creatorcontrib><creatorcontrib>Takahashi, Youhei</creatorcontrib><creatorcontrib>Kodomari, Mitsuo</creatorcontrib><collection>Istex</collection><collection>Biotechnology Research Abstracts</collection><collection>Neurosciences Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of peptide science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hashimoto, Chikao</au><au>Sugimoto, Kazuhiro</au><au>Takahashi, Youhei</au><au>Kodomari, Mitsuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An efficient method for the synthesis of phenacyl ester-protected dipeptides using neutral alumina-supported sodium carbonate 'Na2CO3/n-Al2O3'</atitle><jtitle>Journal of peptide science</jtitle><addtitle>J. Pept. Sci</addtitle><date>2013-10</date><risdate>2013</risdate><volume>19</volume><issue>10</issue><spage>659</spage><epage>662</epage><pages>659-662</pages><issn>1075-2617</issn><eissn>1099-1387</eissn><coden>JPSIEI</coden><abstract>In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐AA2‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using amines for the conversion afforded an unsatisfactory yield with by‐products. On the other hand, the use of neutral alumina‐supported Na2CO3 (Na2CO3/n‐Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products. The application of Na2CO3/n‐Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields. Copyright © 2013 European Peptide Society and John Wiley & Sons, Ltd.
In the synthesis of dipeptides (Boc‐AA1‐AA2‐OPac: AA1 and AA2 represent amino acids) protected by phenacyl (Pac) ester, amines and solid bases as the base for the conversion of the trifluoroacetic acid (TFA) salt of the amino component (TFA·H‐AA2‐OPac) into the corresponding free amino component (H‐AA2‐OPac) were examined. The synthesis of a dipeptide (Boc‐Ala‐Gly‐OPac) using neutral alumina‐supported Na2CO3 (Na2CO3/n‐Al2O3) as a solid base for the conversion provided the dipeptide in a quantitative yield without by‐products compared with the synthesis employing amines. The application of Na2CO3/n‐Al2O3 to the synthesis of some dipeptides protected by Pac ester gave the desired peptides in excellent yields.</abstract><cop>Bognor Regis</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/psc.2544</doi><tpages>4</tpages></addata></record> |
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| subjects | amine neutral alumina-supported sodium carbonate peptide synthesis Peptides phenacyl ester solid base |
| title | An efficient method for the synthesis of phenacyl ester-protected dipeptides using neutral alumina-supported sodium carbonate 'Na2CO3/n-Al2O3' |
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