DK2000474T3 - Fremgangsmåde til produktion af en peptidthioesterforbindelse - Google Patents
Fremgangsmåde til produktion af en peptidthioesterforbindelse Download PDFInfo
- Publication number
- DK2000474T3 DK2000474T3 DK07740944.9T DK07740944T DK2000474T3 DK 2000474 T3 DK2000474 T3 DK 2000474T3 DK 07740944 T DK07740944 T DK 07740944T DK 2000474 T3 DK2000474 T3 DK 2000474T3
- Authority
- DK
- Denmark
- Prior art keywords
- peptide
- acid
- group
- fmoc
- resin
- Prior art date
Links
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- 206010053172 Fatal outcomes Diseases 0.000 description 1
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- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
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- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001356 alkyl thiols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical group OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000000991 chicken egg Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- 239000012024 dehydrating agents Substances 0.000 description 1
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- LMVQFYAHKVDSQV-UHFFFAOYSA-N diphenylmethanamine;2-[4-(hydroxymethyl)-3-methoxyphenoxy]butanoic acid Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1.CCC(C(O)=O)OC1=CC=C(CO)C(OC)=C1 LMVQFYAHKVDSQV-UHFFFAOYSA-N 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000029225 intracellular protein transport Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
- C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
Claims (10)
1. Fremgangsmåde til produktion af en peptidthioesterforbindelse, der er kendetegnet ved at omfatte: (A) frembringelse af et peptid ved hjælp af en fastfasesyntesemetode ved anvendelse af et resin, der er modificeret med en linker som vist ved formel (1), som en fast fase; (B) spaltning af en binding mellem den faste fase og peptidet med mindst én syre valgt blandt fortyndet saltsyre, fortyndet svovlsyre, myresyre og eddikesyre i nærvær af en alkohol til frembringelse af et peptid med en en carboxylgruppe i C-terminalen; og (C) reaktion af en thiolforbindelse med peptidet ved -100 til 0 °C i nærvær af et kondenseringsmiddel i et opløsningsmiddel:
(1) hvor R1 er en Ci-4-alkylgruppe, R2 er et hydrogenatom eller en Ci-4-alkoxygruppe, og n er et helt tal fra 1 til 4.
2. Fremgangsmåde til produktion af et glycopeptid, der har en oligosaccharidkæde med en ubeskyttet hydroxylgruppe og har en carboxylgruppe i C-terminalen, der er kendetegnet ved at omfatte: (A) frembringelse af et glycopeptid ved hjælp af en fastfasesyntesemetode ved anvendelse af et resin, der er modificeret med en linker som vist ved formel (1) , som en fast fase, hvor glycopeptidet er frembragt fra mindst én glycosyleret aminosyre, hvori en oligosaccharidkæde er bundet til en aminosyre; og (B) spaltning af en binding mellem den faste fase og glycopeptidet med mindst én syre valgt blandt fortyndet saltsyre, fortyndet svovlsyre, myresyre og eddikesyre i nærvær af en alkohol.
3. Fremgangsmåde til produktion af en peptidthioesterforbindelse, der er kendetegnet ved at omfatte reaktion af en thiolf orbindelse med et peptid, der har en carboxylgruppe i C-terminalen, i nærvær af et kondenseringsmiddel i et opløsningsmiddel ved -100 til -10 °C.
4. Produktionsmetode ifølge et hvilket som helst af kravene 1 til 3, hvor den N-terminale aminosyre af peptidet er cystein.
5. Produktionsmetode ifølge krav 4, hvor peptidet har en thiolgruppe i cysteinen, der er beskyttet med en fedtopløselige beskyttelsesgruppe.
6. Produktionsmetode ifølge krav 1 eller 2, hvor resinet, der er modificeret med en linker som vist ved formel (1) , er et amino-PEGA-resin, der har en aminogruppe bundet til linkeren, der er vist ved formel (1).
7. Produktionsmetode ifølge krav 1 eller 2, hvor alkoholen er halogenoalkohol.
8. Produktionsmetode ifølge krav 1 eller 3, hvor opløsningsmidlet er mindst ét valgt blandt N,N- dimethylformamid og N-methylpyrrolidon.
9. Produktionsmetode ifølge krav 1 eller 3, hvor kondenseringsmidlet er 1- hydroxybenzotriazol/diisopropylcarbodiimid eller benzotriazol-1-yloxy-trispyrrolidinophosphonium- hexafluorphosphat/diisopropylethylamin.
10. Produktionsmetode ifølge et hvilket som helst af kravene 1 til 9, hvor peptidet er et glycopeptid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006092569 | 2006-03-29 | ||
| PCT/JP2007/057508 WO2007114454A1 (ja) | 2006-03-29 | 2007-03-28 | ペプチドのチオエステル化合物の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2000474T3 true DK2000474T3 (da) | 2018-01-22 |
Family
ID=38563716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK07740944.9T DK2000474T3 (da) | 2006-03-29 | 2007-03-28 | Fremgangsmåde til produktion af en peptidthioesterforbindelse |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8058394B2 (da) |
| EP (1) | EP2000474B1 (da) |
| JP (1) | JP5328345B2 (da) |
| KR (1) | KR101462454B1 (da) |
| CN (1) | CN101437836B (da) |
| AU (1) | AU2007232742B2 (da) |
| CA (1) | CA2647867C (da) |
| DK (1) | DK2000474T3 (da) |
| SG (1) | SG170022A1 (da) |
| TW (2) | TWI450905B (da) |
| WO (1) | WO2007114454A1 (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2766040C (en) | 2009-06-26 | 2018-05-01 | Otsuka Chemical Co., Ltd. | Process for production of peptide thioester |
| US20140377807A1 (en) | 2011-09-26 | 2014-12-25 | Glytech, Inc. | Method for producing polypeptide fragment with high efficiency, which is suitable for ncl method |
| CN104936613B (zh) | 2012-11-30 | 2018-05-22 | 株式会社糖锁工学研究所 | 糖链加成连接子、含有糖链加成连接子与生理活性物质的化合物或其盐、以及其制造方法 |
| HUE034308T2 (en) | 2013-03-21 | 2018-02-28 | Sanofi Aventis Deutschland | Preparation of hydantoin-containing peptide products |
| CN105102427B (zh) | 2013-03-21 | 2018-09-07 | 赛诺菲-安万特德国有限公司 | 含有环状酰亚胺的肽产物的合成 |
| CN106928313B (zh) * | 2015-12-31 | 2020-12-11 | 深圳翰宇药业股份有限公司 | 一种c-端修饰肽的合成方法 |
| US10669306B2 (en) | 2016-02-04 | 2020-06-02 | University Of Washington | Solid supports for use in solid-phase peptide synthesis, kits, and related methods |
| KR102544146B1 (ko) * | 2017-03-02 | 2023-06-15 | 가부시키가이샤 도우사 고가쿠 겐큐쇼 | 아미노산 중합체의 제조방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ295838B6 (cs) * | 1996-09-09 | 2005-11-16 | Zealand Pharma A/S | Způsob výroby peptidů |
| EP2481746A1 (en) * | 2001-06-19 | 2012-08-01 | Otsuka Chemical Co., Ltd. | Process for producing sugar chain asparagine derivative |
| DE10216513A1 (de) * | 2002-04-10 | 2003-10-23 | Joerg Rademann | Polymerverbindung aufgebaut aus linearen Polymerketten |
| US7943763B2 (en) * | 2002-07-05 | 2011-05-17 | Otsuka Chemical Holdings Co., Ltd. | Process for preparing glycopeptides having asparagine-linked oligosaccharides, and the glycopeptides |
| JPWO2005095331A1 (ja) | 2004-03-31 | 2008-02-21 | 塩野義製薬株式会社 | 糖鎖−ペプチド結合剤 |
| CN1254484C (zh) * | 2004-04-30 | 2006-05-03 | 吉林省一心制药有限公司 | 醋酸奥曲肽的固相合成方法 |
| EP1961764B1 (en) | 2005-11-30 | 2011-05-11 | Shionogi Co., Ltd. | Sugar chain adduct of peptide and pharmaceutical comprising the same as active ingredient |
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2007
- 2007-03-28 CN CN2007800158333A patent/CN101437836B/zh active Active
- 2007-03-28 WO PCT/JP2007/057508 patent/WO2007114454A1/ja active Application Filing
- 2007-03-28 US US12/295,113 patent/US8058394B2/en active Active
- 2007-03-28 DK DK07740944.9T patent/DK2000474T3/da active
- 2007-03-28 AU AU2007232742A patent/AU2007232742B2/en active Active
- 2007-03-28 KR KR1020087025264A patent/KR101462454B1/ko active Active
- 2007-03-28 JP JP2008508707A patent/JP5328345B2/ja active Active
- 2007-03-28 SG SG201101270-5A patent/SG170022A1/en unknown
- 2007-03-28 EP EP07740944.9A patent/EP2000474B1/en active Active
- 2007-03-28 CA CA2647867A patent/CA2647867C/en active Active
- 2007-03-29 TW TW099136653A patent/TWI450905B/zh active
- 2007-03-29 TW TW096110938A patent/TW200806686A/zh unknown
Also Published As
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|---|---|
| EP2000474B1 (en) | 2017-11-01 |
| TWI450905B (zh) | 2014-09-01 |
| CA2647867A1 (en) | 2007-10-11 |
| EP2000474A4 (en) | 2012-05-09 |
| US20090137780A1 (en) | 2009-05-28 |
| CA2647867C (en) | 2015-11-03 |
| KR20090007709A (ko) | 2009-01-20 |
| EP2000474A1 (en) | 2008-12-10 |
| AU2007232742A1 (en) | 2007-10-11 |
| WO2007114454A1 (ja) | 2007-10-11 |
| TW201109347A (en) | 2011-03-16 |
| TW200806686A (en) | 2008-02-01 |
| TWI353989B (da) | 2011-12-11 |
| SG170022A1 (en) | 2011-04-29 |
| JP5328345B2 (ja) | 2013-10-30 |
| JPWO2007114454A1 (ja) | 2009-08-20 |
| KR101462454B1 (ko) | 2014-11-17 |
| CN101437836B (zh) | 2013-07-24 |
| US8058394B2 (en) | 2011-11-15 |
| CN101437836A (zh) | 2009-05-20 |
| AU2007232742B2 (en) | 2012-02-02 |
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