Chemo-enzymatic synthesis of semaglutide, liraglutide and GLP-1
The invention relates to a method for preparing a coupling product comprising the sequence Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, comprising enzymatically coupling (a) a peptide C-terminal ester or thioester compri...
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creator | Nuijens, Timo Toplak, Ana Quaedflieg, Peter Jan Leonard Mario |
description | The invention relates to a method for preparing a coupling product comprising the sequence Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, comprising enzymatically coupling (a) a peptide C-terminal ester or thioester comprising a first peptide fragment represented by the formula Pq-Wv- His-X-Glu-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly wherein - P represents a protective group at the N-terminal a-amino function of said peptide C-terminal ester or thioester and q is an integer having a value of 1 or 0; - W represents one or more amino acid residues, which may be the same or different and v is an integer having a value of 1 or more representing the number of amino acid residues W; - X is Ala or an α-amino-isobutyric acid unit (Aib); - Y is Lys, which Lys has a free side-chain ε-amino group or a side-chain ε-amino group that is protected with a protective group or a side-chain ε-amino group that is functionalised with an amino acid or another functional group; - Z is Arg or Lys. |
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and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly wherein - P represents a protective group at the N-terminal a-amino function of said peptide C-terminal ester or thioester and q is an integer having a value of 1 or 0; - W represents one or more amino acid residues, which may be the same or different and v is an integer having a value of 1 or more representing the number of amino acid residues W; - X is Ala or an α-amino-isobutyric acid unit (Aib); - Y is Lys, which Lys has a free side-chain ε-amino group or a side-chain ε-amino group that is protected with a protective group or a side-chain ε-amino group that is functionalised with an amino acid or another functional group; - Z is Arg or Lys.</description><language>eng</language><subject>BEER ; BIOCHEMISTRY ; CHEMISTRY ; COMPOSITIONS THEREOF ; CULTURE MEDIA ; ENZYMOLOGY ; METALLURGY ; MICROBIOLOGY ; MICROORGANISMS OR ENZYMES ; MUTATION OR GENETIC ENGINEERING ; ORGANIC CHEMISTRY ; PEPTIDES ; PROPAGATING, PRESERVING OR MAINTAINING MICROORGANISMS ; SPIRITS ; VINEGAR ; WINE</subject><creationdate>2020</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20201208&DB=EPODOC&CC=US&NR=10858414B2$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25564,76547</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20201208&DB=EPODOC&CC=US&NR=10858414B2$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>Nuijens, Timo</creatorcontrib><creatorcontrib>Toplak, Ana</creatorcontrib><creatorcontrib>Quaedflieg, Peter Jan Leonard Mario</creatorcontrib><title>Chemo-enzymatic synthesis of semaglutide, liraglutide and GLP-1</title><description>The invention relates to a method for preparing a coupling product comprising the sequence Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, comprising enzymatically coupling (a) a peptide C-terminal ester or thioester comprising a first peptide fragment represented by the formula Pq-Wv- His-X-Glu-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly wherein - P represents a protective group at the N-terminal a-amino function of said peptide C-terminal ester or thioester and q is an integer having a value of 1 or 0; - W represents one or more amino acid residues, which may be the same or different and v is an integer having a value of 1 or more representing the number of amino acid residues W; - X is Ala or an α-amino-isobutyric acid unit (Aib); - Y is Lys, which Lys has a free side-chain ε-amino group or a side-chain ε-amino group that is protected with a protective group or a side-chain ε-amino group that is functionalised with an amino acid or another functional group; - Z is Arg or Lys.</description><subject>BEER</subject><subject>BIOCHEMISTRY</subject><subject>CHEMISTRY</subject><subject>COMPOSITIONS THEREOF</subject><subject>CULTURE MEDIA</subject><subject>ENZYMOLOGY</subject><subject>METALLURGY</subject><subject>MICROBIOLOGY</subject><subject>MICROORGANISMS OR ENZYMES</subject><subject>MUTATION OR GENETIC ENGINEERING</subject><subject>ORGANIC CHEMISTRY</subject><subject>PEPTIDES</subject><subject>PROPAGATING, PRESERVING OR MAINTAINING MICROORGANISMS</subject><subject>SPIRITS</subject><subject>VINEGAR</subject><subject>WINE</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2020</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZLB3zkjNzddNzauqzE0syUxWKK7MK8lILc4sVshPUyhOzU1MzyktyUxJ1VHIySyCcRQS81IU3H0CdA15GFjTEnOKU3mhNDeDoptriLOHbmpBfnxqcUFicmpeakl8aLChgYWphYmhiZORMTFqAHTEMI4</recordid><startdate>20201208</startdate><enddate>20201208</enddate><creator>Nuijens, Timo</creator><creator>Toplak, Ana</creator><creator>Quaedflieg, Peter Jan Leonard Mario</creator><scope>EVB</scope></search><sort><creationdate>20201208</creationdate><title>Chemo-enzymatic synthesis of semaglutide, liraglutide and GLP-1</title><author>Nuijens, Timo ; Toplak, Ana ; Quaedflieg, Peter Jan Leonard Mario</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_US10858414B23</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>2020</creationdate><topic>BEER</topic><topic>BIOCHEMISTRY</topic><topic>CHEMISTRY</topic><topic>COMPOSITIONS THEREOF</topic><topic>CULTURE MEDIA</topic><topic>ENZYMOLOGY</topic><topic>METALLURGY</topic><topic>MICROBIOLOGY</topic><topic>MICROORGANISMS OR ENZYMES</topic><topic>MUTATION OR GENETIC ENGINEERING</topic><topic>ORGANIC CHEMISTRY</topic><topic>PEPTIDES</topic><topic>PROPAGATING, PRESERVING OR MAINTAINING MICROORGANISMS</topic><topic>SPIRITS</topic><topic>VINEGAR</topic><topic>WINE</topic><toplevel>online_resources</toplevel><creatorcontrib>Nuijens, Timo</creatorcontrib><creatorcontrib>Toplak, Ana</creatorcontrib><creatorcontrib>Quaedflieg, Peter Jan Leonard Mario</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>Nuijens, Timo</au><au>Toplak, Ana</au><au>Quaedflieg, Peter Jan Leonard Mario</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Chemo-enzymatic synthesis of semaglutide, liraglutide and GLP-1</title><date>2020-12-08</date><risdate>2020</risdate><abstract>The invention relates to a method for preparing a coupling product comprising the sequence Pq-Wv-His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, comprising enzymatically coupling (a) a peptide C-terminal ester or thioester comprising a first peptide fragment represented by the formula Pq-Wv- His-X-Glu-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly wherein - P represents a protective group at the N-terminal a-amino function of said peptide C-terminal ester or thioester and q is an integer having a value of 1 or 0; - W represents one or more amino acid residues, which may be the same or different and v is an integer having a value of 1 or more representing the number of amino acid residues W; - X is Ala or an α-amino-isobutyric acid unit (Aib); - Y is Lys, which Lys has a free side-chain ε-amino group or a side-chain ε-amino group that is protected with a protective group or a side-chain ε-amino group that is functionalised with an amino acid or another functional group; - Z is Arg or Lys.</abstract><oa>free_for_read</oa></addata></record> |
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subjects | BEER BIOCHEMISTRY CHEMISTRY COMPOSITIONS THEREOF CULTURE MEDIA ENZYMOLOGY METALLURGY MICROBIOLOGY MICROORGANISMS OR ENZYMES MUTATION OR GENETIC ENGINEERING ORGANIC CHEMISTRY PEPTIDES PROPAGATING, PRESERVING OR MAINTAINING MICROORGANISMS SPIRITS VINEGAR WINE |
title | Chemo-enzymatic synthesis of semaglutide, liraglutide and GLP-1 |
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