One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams
Abstract α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam rin...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2020-12, Vol.52 (23), p.3657-3666 |
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| container_title | Synthesis (Stuttgart) |
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| creator | Tarui, Atsushi Ueo, Masakazu Morikawa, Marino Tsuta, Masahiko Iwasaki, Sumika Morishita, Noriko Karuo, Yukiko Sato, Kazuyuki Kawai, Kentaro Omote, Masaaki |
| description | Abstract
α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit. |
| doi_str_mv | 10.1055/s-0040-1707238 |
| format | Article |
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α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0040-1707238</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><ispartof>Synthesis (Stuttgart), 2020-12, Vol.52 (23), p.3657-3666</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c317t-b7e6599dc903e3430e0c82c563f5ad1b4772ed3501e1bc15c4682c44762524283</citedby><cites>FETCH-LOGICAL-c317t-b7e6599dc903e3430e0c82c563f5ad1b4772ed3501e1bc15c4682c44762524283</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1707238.pdf$$EPDF$$P50$$Gthieme$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0040-1707238$$EHTML$$P50$$Gthieme$$Hfree_for_read</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Tarui, Atsushi</creatorcontrib><creatorcontrib>Ueo, Masakazu</creatorcontrib><creatorcontrib>Morikawa, Marino</creatorcontrib><creatorcontrib>Tsuta, Masahiko</creatorcontrib><creatorcontrib>Iwasaki, Sumika</creatorcontrib><creatorcontrib>Morishita, Noriko</creatorcontrib><creatorcontrib>Karuo, Yukiko</creatorcontrib><creatorcontrib>Sato, Kazuyuki</creatorcontrib><creatorcontrib>Kawai, Kentaro</creatorcontrib><creatorcontrib>Omote, Masaaki</creatorcontrib><title>One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit.</description><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>0U6</sourceid><recordid>eNp1kM1Kw0AUhQdRsFa3rvMA3nrnL5MspVoVCilqwd2QTG5sSpOUTLroY9UH6TOZ0G5dHbjnnMvhY-ye44Sj1o8eEBUCN2iEjC7YiCtpQHD8vmQjRBmDiSJ-zW68XyMOoXjEZklNsGi64KOsfyDZUt1rsKBtV-YUfO7rbkW-9MHSD_fj4eF4gOey2OyatoHjL8xT16WVv2VXRbrxdHfWMVvOXr6mbzBPXt-nT3NwkpsOMkOhjuPcxShJKomELhJOh7LQac4zZYygXGrkxDPHtVNhbytlQqGFEpEcs8npr2sb71sq7LYtq7TdW452oGC9HSjYM4W-AKdCtyqpIrtudm3dL_wv_wcb0l4t</recordid><startdate>20201201</startdate><enddate>20201201</enddate><creator>Tarui, Atsushi</creator><creator>Ueo, Masakazu</creator><creator>Morikawa, Marino</creator><creator>Tsuta, Masahiko</creator><creator>Iwasaki, Sumika</creator><creator>Morishita, Noriko</creator><creator>Karuo, Yukiko</creator><creator>Sato, Kazuyuki</creator><creator>Kawai, Kentaro</creator><creator>Omote, Masaaki</creator><general>Georg Thieme Verlag</general><scope>0U6</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20201201</creationdate><title>One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams</title><author>Tarui, Atsushi ; Ueo, Masakazu ; Morikawa, Marino ; Tsuta, Masahiko ; Iwasaki, Sumika ; Morishita, Noriko ; Karuo, Yukiko ; Sato, Kazuyuki ; Kawai, Kentaro ; Omote, Masaaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c317t-b7e6599dc903e3430e0c82c563f5ad1b4772ed3501e1bc15c4682c44762524283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tarui, Atsushi</creatorcontrib><creatorcontrib>Ueo, Masakazu</creatorcontrib><creatorcontrib>Morikawa, Marino</creatorcontrib><creatorcontrib>Tsuta, Masahiko</creatorcontrib><creatorcontrib>Iwasaki, Sumika</creatorcontrib><creatorcontrib>Morishita, Noriko</creatorcontrib><creatorcontrib>Karuo, Yukiko</creatorcontrib><creatorcontrib>Sato, Kazuyuki</creatorcontrib><creatorcontrib>Kawai, Kentaro</creatorcontrib><creatorcontrib>Omote, Masaaki</creatorcontrib><collection>Thieme Connect Journals Open Access</collection><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tarui, Atsushi</au><au>Ueo, Masakazu</au><au>Morikawa, Marino</au><au>Tsuta, Masahiko</au><au>Iwasaki, Sumika</au><au>Morishita, Noriko</au><au>Karuo, Yukiko</au><au>Sato, Kazuyuki</au><au>Kawai, Kentaro</au><au>Omote, Masaaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2020-12-01</date><risdate>2020</risdate><volume>52</volume><issue>23</issue><spage>3657</spage><epage>3666</epage><pages>3657-3666</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
α,α-Difluoro-β-lactams successfully underwent ring-opening aminolysis with various amino acids in 2,2,2-trifluoroethanol to afford fluorine-containing peptides. In this aminolysis, it was found that 2,2,2-trifluoroethanol first attacked the α,α-difluoro-β-lactams with cleavage of lactam ring to form the corresponding open-chain 2,2,2-trifluoroethyl esters as reactive intermediates. The trifluoroethyl esters were more electrophilic compared with the corresponding methyl ester and thereby accelerated the aminolysis with various amino acids to form β-amino acid peptides with α,α-difluoromethylene unit.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0040-1707238</doi><tpages>10</tpages><oa>free_for_read</oa></addata></record> |
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| title | One-Pot Ring-Opening Peptide Synthesis Using α,α-Difluoro-β-Lactams |
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