ES2531054T3 - Condensación de fragmento de oligopéptido de cadena lateral protegida mediante el uso de subtilisinas en disolventes orgánicos - Google Patents
Condensación de fragmento de oligopéptido de cadena lateral protegida mediante el uso de subtilisinas en disolventes orgánicos Download PDFInfo
- Publication number
- ES2531054T3 ES2531054T3 ES12157571T ES12157571T ES2531054T3 ES 2531054 T3 ES2531054 T3 ES 2531054T3 ES 12157571 T ES12157571 T ES 12157571T ES 12157571 T ES12157571 T ES 12157571T ES 2531054 T3 ES2531054 T3 ES 2531054T3
- Authority
- ES
- Spain
- Prior art keywords
- amino acid
- side chain
- oligopeptide
- acid residues
- terminal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 108010038807 Oligopeptides Proteins 0.000 title abstract 6
- 102000015636 Oligopeptides Human genes 0.000 title abstract 6
- 239000003960 organic solvent Substances 0.000 title abstract 3
- 102000005158 Subtilisins Human genes 0.000 title 1
- 108010056079 Subtilisins Proteins 0.000 title 1
- 230000005494 condensation Effects 0.000 title 1
- 238000009833 condensation Methods 0.000 title 1
- 239000012634 fragment Substances 0.000 title 1
- 125000000539 amino acid group Chemical group 0.000 abstract 5
- 238000005859 coupling reaction Methods 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 210000004899 c-terminal region Anatomy 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000012038 nucleophile Substances 0.000 abstract 2
- 108090000765 processed proteins & peptides Chemical group 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000787 Subtilisin Proteins 0.000 abstract 1
- 150000001413 amino acids Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 230000002255 enzymatic effect Effects 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P21/00—Preparation of peptides or proteins
-
- 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
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- 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
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
- C07K1/026—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution by fragment condensation in solution
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
Método para la síntesis enzimática de un oligopéptido, que comprende acoplar i.) un éster de oligopéptido que comprende 4 o más residuos de aminoácidos, - que comprende al menos dos residuos de aminoácidos cada uno con una funcionalidad de cadena lateral que está protegida con un grupo protector, y que comprende un éster C10 terminal activado representado por la fórmula C(>=O)-O-CX2-C(>=O)N-R1R2, en donde cada X representa independientemente un átomo de hidrógeno o un grupo alquilo o un grupo arilo y R1 representa un átomo de hidrógeno o un grupo alquilo o un grupo arilo y R2 representa un átomo de hidrógeno o un grupo alquilo o un grupo arilo o un aminoácido o un residuo de péptido con una funcionalidad de carboxiamida C-terminal o de ácido carboxílico, opcionalmente protegida en la funcionalidad de cadena lateral del residuo de aminoácido o uno o más de las funcionalidades de cadenas laterales del residuo de péptido, - y en donde el éster de oligopéptido opcionalmente comprende una protección N-terminal, con ii.) un nucleófilo de oligopéptido que comprende 4 o más residuos de aminoácidos, - que comprende un grupo amina N-terminal, y al menos dos residuos de aminoácidos cada uno con una funcionalidad de cadena lateral, que está protegida con un grupo protector y - en donde el nucleófilo de oligopéptido opcionalmente comprende protección C-terminal, cuyo acoplamiento se lleva a cabo en un disolvente orgánico o una mezcla de disolventes orgánicos que comprende 0.1 % vol o menos de agua con relación a la cantidad total de líquidos en la cual tiene lugar predominantemente la reacción de acoplamiento, en presencia de una subtilisina y en donde se elimina el agua que se libera por la enzima durante la reacción de acoplamiento.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12157571.6A EP2634193B1 (en) | 2012-02-29 | 2012-02-29 | Side-chain protected oligopeptide fragment condensation using subtilisins in organic solvents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2531054T3 true ES2531054T3 (es) | 2015-03-10 |
Family
ID=47884473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12157571T Active ES2531054T3 (es) | 2012-02-29 | 2012-02-29 | Condensación de fragmento de oligopéptido de cadena lateral protegida mediante el uso de subtilisinas en disolventes orgánicos |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9598714B2 (es) |
| EP (1) | EP2634193B1 (es) |
| JP (1) | JP2015508666A (es) |
| CN (1) | CN104284901A (es) |
| CA (1) | CA2864865A1 (es) |
| DK (1) | DK2634193T3 (es) |
| ES (1) | ES2531054T3 (es) |
| IN (1) | IN2014MN01770A (es) |
| WO (1) | WO2013129926A1 (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2657250T3 (en) * | 2010-12-21 | 2017-12-11 | Cj Cheiljedang Corp | Polypeptide variant having homoserine acetyl transferase activity and microorganism expressing this |
| JP7017409B2 (ja) * | 2014-10-10 | 2022-02-08 | エンザイペプ ビー．ブイ． | 加水分解に対する合成の比が改善したスブチリシン変異体を使用するペプチド断片縮合及び環化 |
| US10752931B2 (en) * | 2015-07-09 | 2020-08-25 | Enzypep B.V. | Designing an enzymatic peptide fragment condensation strategy |
| US10827880B2 (en) | 2016-02-03 | 2020-11-10 | Conair Corporation | Food processor and modular lid assembly therefor |
| AU2019319032B2 (en) | 2018-08-09 | 2022-06-02 | F. Hoffmann-La Roche Ag | Cleavable linker for peptide synthesis |
| WO2023086502A1 (en) * | 2021-11-12 | 2023-05-19 | Virginia Tech Intellectual Properties, Inc. | Hydrolyzed protein serum replacement compositions |
| KR102886982B1 (ko) | 2022-03-11 | 2025-11-17 | 강성구 | 고상 유기 합성용 기재 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6509727A (es) * | 1965-07-28 | 1967-01-30 | ||
| US5316935A (en) | 1992-04-06 | 1994-05-31 | California Institute Of Technology | Subtilisin variants suitable for hydrolysis and synthesis in organic media |
| MX2007012157A (es) * | 2005-04-01 | 2008-03-14 | Intezyne Technologies Llc | Micelas polimericas para suministro de farmacos. |
| EA019536B1 (ru) * | 2008-11-19 | 2014-04-30 | ДСМ АйПи АССЕТС Б.В. | Синтез пептидов с использованием энзиматической активации и конденсации |
-
2012
- 2012-02-29 ES ES12157571T patent/ES2531054T3/es active Active
- 2012-02-29 DK DK12157571T patent/DK2634193T3/en active
- 2012-02-29 EP EP12157571.6A patent/EP2634193B1/en not_active Not-in-force
-
2013
- 2013-02-28 WO PCT/NL2013/050125 patent/WO2013129926A1/en not_active Ceased
- 2013-02-28 JP JP2014559858A patent/JP2015508666A/ja active Pending
- 2013-02-28 CA CA2864865A patent/CA2864865A1/en not_active Abandoned
- 2013-02-28 CN CN201380022510.2A patent/CN104284901A/zh active Pending
- 2013-02-28 IN IN1770MUN2014 patent/IN2014MN01770A/en unknown
- 2013-02-28 US US14/379,789 patent/US9598714B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015508666A (ja) | 2015-03-23 |
| CN104284901A (zh) | 2015-01-14 |
| US9598714B2 (en) | 2017-03-21 |
| CA2864865A1 (en) | 2013-09-06 |
| EP2634193B1 (en) | 2015-01-14 |
| EP2634193A1 (en) | 2013-09-04 |
| DK2634193T3 (en) | 2015-03-02 |
| IN2014MN01770A (es) | 2015-07-03 |
| WO2013129926A1 (en) | 2013-09-06 |
| US20150037840A1 (en) | 2015-02-05 |
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