CHEMO-ENZYMATIC SYNTHESIS OF LIRAGLUTIDE, SEMAGLUTIDE AND GLP-1
To provide a novel method of enzymatically synthesizing GLP-1 or an analogue thereof, in particular Liraglutide or Semaglutide.SOLUTION: The invention relates to a method for synthesizing a peptide comprising the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Gl...
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| creator | ANA TOPLAK PETER JAN LEONARD MARIO QUAEDFLIEG TIMO NUIJENS |
| description | To provide a novel method of enzymatically synthesizing GLP-1 or an analogue thereof, in particular Liraglutide or Semaglutide.SOLUTION: The invention relates to a method for synthesizing a peptide comprising the sequence 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 comprising the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, where X is Ala or an α-amino-isobutyric acid (Aib) residue; Y is Lys, which Lys has a free side-chain ε-amino group or of which Lys the side-chain ε-amino group is protected with a protective group or of which Lys the side-chain ε-amino group is functionalized with an amino acid or another functional group; Z is Arg or Lys.SELECTED DRAWING: None
【課題】ＧＬＰ－１又はその類似体、特にリラグルチド又はセマグルチドを酵素的に合成する新規の方法を提供すること。【解決手段】本発明は、（ａ）配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－（チオ）エステルを含む第１のペプチド断片を含むペプチドＣ末端エステル又はチオエステルと、（ｂ）配列Ｈ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含む第２のペプチド断片を含むＮ末端非保護アミンを有するペプチド求核剤とを酵素的にカップリングさせることを含む、配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含むペプチドを合成するための方法に関し、ここで、ＸはＡｌａ又はα－アミノ－イソ酪酸（Ａｉｂ）残基であり、ＹはＬｙｓであり、このＬｙｓは遊離側鎖ε－アミノ基を有するか、或いはＬｙｓの側鎖ε－アミノ基は保護基によって保護されているか、或いはＬｙｓの側鎖ε－アミノ基はアミノ酸又は別の官能基によって官能化されており、ＺはＡｒｇ又はＬｙｓである。【選択図】なし |
| format | Patent |
| fullrecord | <record><control><sourceid>epo_EVB</sourceid><recordid>TN_cdi_epo_espacenet_JP2024010221A</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>JP2024010221A</sourcerecordid><originalsourceid>FETCH-epo_espacenet_JP2024010221A3</originalsourceid><addsrcrecordid>eNrjZLB39nD19dd19YuK9HUM8XRWCI70C_FwDfYMVvB3U_DxDHJ09wkN8XRx1VEIdvWFcRQc_VwU3H0CdA15GFjTEnOKU3mhNDeDkptriLOHbmpBfnxqcUFicmpeakm8V4CRgZGJgaGBkZGhozFRigDPrSqM</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>patent</recordtype></control><display><type>patent</type><title>CHEMO-ENZYMATIC SYNTHESIS OF LIRAGLUTIDE, SEMAGLUTIDE AND GLP-1</title><source>esp@cenet</source><creator>ANA TOPLAK ; PETER JAN LEONARD MARIO QUAEDFLIEG ; TIMO NUIJENS</creator><creatorcontrib>ANA TOPLAK ; PETER JAN LEONARD MARIO QUAEDFLIEG ; TIMO NUIJENS</creatorcontrib><description>To provide a novel method of enzymatically synthesizing GLP-1 or an analogue thereof, in particular Liraglutide or Semaglutide.SOLUTION: The invention relates to a method for synthesizing a peptide comprising the sequence 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 comprising the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, where X is Ala or an α-amino-isobutyric acid (Aib) residue; Y is Lys, which Lys has a free side-chain ε-amino group or of which Lys the side-chain ε-amino group is protected with a protective group or of which Lys the side-chain ε-amino group is functionalized with an amino acid or another functional group; Z is Arg or Lys.SELECTED DRAWING: None
【課題】ＧＬＰ－１又はその類似体、特にリラグルチド又はセマグルチドを酵素的に合成する新規の方法を提供すること。【解決手段】本発明は、（ａ）配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－（チオ）エステルを含む第１のペプチド断片を含むペプチドＣ末端エステル又はチオエステルと、（ｂ）配列Ｈ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含む第２のペプチド断片を含むＮ末端非保護アミンを有するペプチド求核剤とを酵素的にカップリングさせることを含む、配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含むペプチドを合成するための方法に関し、ここで、ＸはＡｌａ又はα－アミノ－イソ酪酸（Ａｉｂ）残基であり、ＹはＬｙｓであり、このＬｙｓは遊離側鎖ε－アミノ基を有するか、或いはＬｙｓの側鎖ε－アミノ基は保護基によって保護されているか、或いはＬｙｓの側鎖ε－アミノ基はアミノ酸又は別の官能基によって官能化されており、ＺはＡｒｇ又はＬｙｓである。【選択図】なし</description><language>eng ; jpn</language><subject>BEER ; BIOCHEMISTRY ; CHEMISTRY ; ENZYMOLOGY ; FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE ; METALLURGY ; MICROBIOLOGY ; MUTATION OR GENETIC ENGINEERING ; SPIRITS ; VINEGAR ; WINE</subject><creationdate>2024</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=20240123&DB=EPODOC&CC=JP&NR=2024010221A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25543,76293</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=20240123&DB=EPODOC&CC=JP&NR=2024010221A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>ANA TOPLAK</creatorcontrib><creatorcontrib>PETER JAN LEONARD MARIO QUAEDFLIEG</creatorcontrib><creatorcontrib>TIMO NUIJENS</creatorcontrib><title>CHEMO-ENZYMATIC SYNTHESIS OF LIRAGLUTIDE, SEMAGLUTIDE AND GLP-1</title><description>To provide a novel method of enzymatically synthesizing GLP-1 or an analogue thereof, in particular Liraglutide or Semaglutide.SOLUTION: The invention relates to a method for synthesizing a peptide comprising the sequence 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 comprising the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, where X is Ala or an α-amino-isobutyric acid (Aib) residue; Y is Lys, which Lys has a free side-chain ε-amino group or of which Lys the side-chain ε-amino group is protected with a protective group or of which Lys the side-chain ε-amino group is functionalized with an amino acid or another functional group; Z is Arg or Lys.SELECTED DRAWING: None
【課題】ＧＬＰ－１又はその類似体、特にリラグルチド又はセマグルチドを酵素的に合成する新規の方法を提供すること。【解決手段】本発明は、（ａ）配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－（チオ）エステルを含む第１のペプチド断片を含むペプチドＣ末端エステル又はチオエステルと、（ｂ）配列Ｈ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含む第２のペプチド断片を含むＮ末端非保護アミンを有するペプチド求核剤とを酵素的にカップリングさせることを含む、配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含むペプチドを合成するための方法に関し、ここで、ＸはＡｌａ又はα－アミノ－イソ酪酸（Ａｉｂ）残基であり、ＹはＬｙｓであり、このＬｙｓは遊離側鎖ε－アミノ基を有するか、或いはＬｙｓの側鎖ε－アミノ基は保護基によって保護されているか、或いはＬｙｓの側鎖ε－アミノ基はアミノ酸又は別の官能基によって官能化されており、ＺはＡｒｇ又はＬｙｓである。【選択図】なし</description><subject>BEER</subject><subject>BIOCHEMISTRY</subject><subject>CHEMISTRY</subject><subject>ENZYMOLOGY</subject><subject>FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE</subject><subject>METALLURGY</subject><subject>MICROBIOLOGY</subject><subject>MUTATION OR GENETIC ENGINEERING</subject><subject>SPIRITS</subject><subject>VINEGAR</subject><subject>WINE</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>2024</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZLB39nD19dd19YuK9HUM8XRWCI70C_FwDfYMVvB3U_DxDHJ09wkN8XRx1VEIdvWFcRQc_VwU3H0CdA15GFjTEnOKU3mhNDeDkptriLOHbmpBfnxqcUFicmpeakm8V4CRgZGJgaGBkZGhozFRigDPrSqM</recordid><startdate>20240123</startdate><enddate>20240123</enddate><creator>ANA TOPLAK</creator><creator>PETER JAN LEONARD MARIO QUAEDFLIEG</creator><creator>TIMO NUIJENS</creator><scope>EVB</scope></search><sort><creationdate>20240123</creationdate><title>CHEMO-ENZYMATIC SYNTHESIS OF LIRAGLUTIDE, SEMAGLUTIDE AND GLP-1</title><author>ANA TOPLAK ; PETER JAN LEONARD MARIO QUAEDFLIEG ; TIMO NUIJENS</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_JP2024010221A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; jpn</language><creationdate>2024</creationdate><topic>BEER</topic><topic>BIOCHEMISTRY</topic><topic>CHEMISTRY</topic><topic>ENZYMOLOGY</topic><topic>FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE</topic><topic>METALLURGY</topic><topic>MICROBIOLOGY</topic><topic>MUTATION OR GENETIC ENGINEERING</topic><topic>SPIRITS</topic><topic>VINEGAR</topic><topic>WINE</topic><toplevel>online_resources</toplevel><creatorcontrib>ANA TOPLAK</creatorcontrib><creatorcontrib>PETER JAN LEONARD MARIO QUAEDFLIEG</creatorcontrib><creatorcontrib>TIMO NUIJENS</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>ANA TOPLAK</au><au>PETER JAN LEONARD MARIO QUAEDFLIEG</au><au>TIMO NUIJENS</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>CHEMO-ENZYMATIC SYNTHESIS OF LIRAGLUTIDE, SEMAGLUTIDE AND GLP-1</title><date>2024-01-23</date><risdate>2024</risdate><abstract>To provide a novel method of enzymatically synthesizing GLP-1 or an analogue thereof, in particular Liraglutide or Semaglutide.SOLUTION: The invention relates to a method for synthesizing a peptide comprising the sequence 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 comprising the sequence His-X-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-(thio)ester; and (b) a peptide nucleophile having an N-terminally unprotected amine comprising a second peptide fragment comprising the sequence H-Ser-Tyr-Leu-Glu-Gly-Gln-Ala-Ala-Y-Glu-Phe-lle-Ala-Trp-Leu-Val-Z-Gly-Arg-Gly, where X is Ala or an α-amino-isobutyric acid (Aib) residue; Y is Lys, which Lys has a free side-chain ε-amino group or of which Lys the side-chain ε-amino group is protected with a protective group or of which Lys the side-chain ε-amino group is functionalized with an amino acid or another functional group; Z is Arg or Lys.SELECTED DRAWING: None
【課題】ＧＬＰ－１又はその類似体、特にリラグルチド又はセマグルチドを酵素的に合成する新規の方法を提供すること。【解決手段】本発明は、（ａ）配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－（チオ）エステルを含む第１のペプチド断片を含むペプチドＣ末端エステル又はチオエステルと、（ｂ）配列Ｈ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含む第２のペプチド断片を含むＮ末端非保護アミンを有するペプチド求核剤とを酵素的にカップリングさせることを含む、配列Ｈｉｓ－Ｘ－Ｇｌｕ－Ｇｌｙ－Ｔｈｒ－Ｐｈｅ－Ｔｈｒ－Ｓｅｒ－Ａｓｐ－Ｖａｌ－Ｓｅｒ－Ｓｅｒ－Ｔｙｒ－Ｌｅｕ－Ｇｌｕ－Ｇｌｙ－Ｇｌｎ－Ａｌａ－Ａｌａ－Ｙ－Ｇｌｕ－Ｐｈｅ－Ｉｌｅ－Ａｌａ－Ｔｒｐ－Ｌｅｕ－Ｖａｌ－Ｚ－Ｇｌｙ－Ａｒｇ－Ｇｌｙを含むペプチドを合成するための方法に関し、ここで、ＸはＡｌａ又はα－アミノ－イソ酪酸（Ａｉｂ）残基であり、ＹはＬｙｓであり、このＬｙｓは遊離側鎖ε－アミノ基を有するか、或いはＬｙｓの側鎖ε－アミノ基は保護基によって保護されているか、或いはＬｙｓの側鎖ε－アミノ基はアミノ酸又は別の官能基によって官能化されており、ＺはＡｒｇ又はＬｙｓである。【選択図】なし</abstract><oa>free_for_read</oa></addata></record> |
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| subjects | BEER BIOCHEMISTRY CHEMISTRY ENZYMOLOGY FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIREDCHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERSFROM A RACEMIC MIXTURE METALLURGY MICROBIOLOGY MUTATION OR GENETIC ENGINEERING SPIRITS VINEGAR WINE |
| title | CHEMO-ENZYMATIC SYNTHESIS OF LIRAGLUTIDE, SEMAGLUTIDE AND GLP-1 |
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