HRP20110489T1 - Postupak kemo-selektivne enzimske hidrolize diesterskog spoja za pripremu spoja monoestera monokiseline - Google Patents
Postupak kemo-selektivne enzimske hidrolize diesterskog spoja za pripremu spoja monoestera monokiseline Download PDFInfo
- Publication number
- HRP20110489T1 HRP20110489T1 HR20110489T HRP20110489T HRP20110489T1 HR P20110489 T1 HRP20110489 T1 HR P20110489T1 HR 20110489 T HR20110489 T HR 20110489T HR P20110489 T HRP20110489 T HR P20110489T HR P20110489 T1 HRP20110489 T1 HR P20110489T1
- Authority
- HR
- Croatia
- Prior art keywords
- lipase
- compound
- previous
- formula
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 23
- 150000001875 compounds Chemical class 0.000 title claims abstract 7
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 title claims abstract 5
- 230000007071 enzymatic hydrolysis Effects 0.000 title claims abstract 4
- -1 diester compound Chemical class 0.000 title abstract 2
- 238000002512 chemotherapy Methods 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 claims abstract 4
- 238000003786 synthesis reaction Methods 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 3
- 102000004882 Lipase Human genes 0.000 claims 7
- 108090001060 Lipase Proteins 0.000 claims 7
- 239000004367 Lipase Substances 0.000 claims 7
- 235000019421 lipase Nutrition 0.000 claims 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 239000007853 buffer solution Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 2
- 239000006184 cosolvent Substances 0.000 claims 2
- 239000000243 solution Substances 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims 2
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical compound C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000019626 lipase activity Nutrition 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229910000160 potassium phosphate Inorganic materials 0.000 claims 1
- 235000011009 potassium phosphates Nutrition 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 229960002354 repaglinide Drugs 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract 2
- 108090000790 Enzymes Proteins 0.000 abstract 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
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
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
Abstract
Postupak sinteze spoja formule (I) prema donjoj Shemi A: gdje R1, R2 i R3, koji mogu biti identični ili različiti, predstavljaju alkilnu skupinu, naznačen time što je to reakcija enzimske hidrolize koja uključuje dovođenje spoja formule (II) u doticaj s lipazom radi dobivanja spoja formule (I). Patent sadrži još 19 patentnih zahtjeva.
Claims (21)
1. Postupak sinteze spoja formule (I) prema donjoj Shemi A:
[image]
gdje R1, R2 i R3, koji mogu biti identični ili različiti, predstavljaju alkilnu skupinu, naznačen time što je to reakcija enzimske hidrolize koja uključuje dovođenje spoja formule (II) u doticaj s lipazom radi dobivanja spoja formule (I).
2. Postupak prema zahtjevu 1, naznačen time što se reakcija hidrolize izvodi u otopini kontrolirane pH vrijednosti, točnije pomoću otopine pufera, u prisutnosti ili bez organskog ko-otapala.
3. Postupak prema zahtjevu 1 ili zahtjevu 2, naznačen time što je korištena lipaza prisutna ili u čvrstom obliku ili u otopini, ili u suspenziji, ili u obliku imobliziranom na inertnom nosaču.
4. Postupak prema jednom od zahtjeva 1 do 3, naznačen time što se izabrana lipaza može koristiti izravno ili u obliku koji je dostupan na tržištu ili nakon pročišćavanja.
5. Postupak prema jednom od prethodnih zahtjeva, naznačen time što se pH vrijednost tijekom reakcije kontrolira tako da ne utječe na aktivnost lipaze, točnije, ta se pH vrijednost tijekom reakcije održava između 6 i 8.
6. Postupak prema jednom od prethodnih zahtjeva, naznačen time što je broj ciklusa uporabe izabrane lipaze između 1 i 5.
7. Postupak prema jednom od prethodnih zahtjeva, naznačen time što je omjer količine korištene lipaze prema količini supstrata, izraženo kao vrijednost težina/težina (E/S omjer), između 1/10 000 i 20/100, poželjno između 1/1000 i 5/100.
8. Postupak prema jednom od prethodnih zahtjeva, naznačen time što je početna koncentracija početnog materijala između 1 kg/l i 50 g/l.
9. Postupak prema jednom od prethodnih zahtjeva, naznačen time što se enzimska hidroliza izvodi pri temperaturi između 10°C i 70°C.
10. Postupak prema jednom od prethodnih zahtjeva, naznačen time što se pH reakcijskog medija kontrolira tako da se dodaje jaka lužina, posebno hidroksid ili alkoksid alkalijskog metala.
11. Postupak prema jednom od prethodnih zahtjeva, naznačen time što nema organskog ko-otapala.
12. Postupak prema jednom od prethodnih zahtjeva, naznačen time što je svaka skupina R1, R2 i R3 istodobno ethil.
13. Postupak prema jednom od zahtjeva 1 do 12, naznačen time što the lipase used is obtained from Candida
14. antarctica type B.
15. Postupak prema jednom od zahtjeva 2 do 13, naznačen time što je otopina pufera vodena otopina na bazi fosfata, karbonata ili sulfata, s pH vrijednošću između 6 i 8, posebno vodena otopina na bazi kalijevog fosfata.
16. Postupak prema zahtjevu 14, naznačen time što je početna pH vrijednost otopine pufera oko 7.2.
17. Postupak prema jednom od zahtjeva 2 do 13, naznačen time što se pH kontrolira dodavanjem vodene otopine jake lužine, posebno natrijevog hidroksida.
18. Postupak prema jednom od zahtjeva 1 do 16, naznačen time što je temperatura reakcije poželjno oko 45°C.
19. Postupak prema jednom od zahtjeva 1 do 17, naznačen time što je početna koncentracija početnog materijala formule (II) oko 400 g/l.
20. Postupak prema jednom od zahtjeva 1 do 18, naznačen time što je količina lipaze između 1 g/l i 10 g/l.
21. Postupak prema jednom od zahtjeva 1 do 19, naznačen time što se spoj formule (I) koristi kao međuprodukt u sintezi za pripremu repaglinida.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0752792A FR2911603B1 (fr) | 2007-01-22 | 2007-01-22 | Procede d'hydrolyse enzymatique chimioselectif d'un compose diester pour la preparation d'un compose monoester monoacide |
| PCT/FR2008/050095 WO2008110706A2 (fr) | 2007-01-22 | 2008-01-22 | Procede d'hydrolyse enzymatique chimioselectif d'un compose diester pour la preparation d'un compose monoester monoacide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110489T1 true HRP20110489T1 (hr) | 2011-07-31 |
Family
ID=38093134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110489T HRP20110489T1 (hr) | 2007-01-22 | 2011-07-01 | Postupak kemo-selektivne enzimske hidrolize diesterskog spoja za pripremu spoja monoestera monokiseline |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8198054B2 (hr) |
| EP (1) | EP2121950B1 (hr) |
| CN (1) | CN101652483B (hr) |
| AT (1) | ATE504657T1 (hr) |
| DE (1) | DE602008006038D1 (hr) |
| DK (1) | DK2121950T3 (hr) |
| ES (1) | ES2363573T3 (hr) |
| FR (1) | FR2911603B1 (hr) |
| HR (1) | HRP20110489T1 (hr) |
| IL (1) | IL199910A (hr) |
| PL (1) | PL2121950T3 (hr) |
| PT (1) | PT2121950E (hr) |
| SI (1) | SI2121950T1 (hr) |
| WO (1) | WO2008110706A2 (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104404098A (zh) * | 2014-12-15 | 2015-03-11 | 苏州汉酶生物技术有限公司 | 一种硫辛酸的生物制备方法 |
| CN110483292A (zh) * | 2019-08-29 | 2019-11-22 | 杭州中美华东制药有限公司 | 一种瑞格列奈关键中间体的制备方法 |
| CN111471725B (zh) * | 2020-04-29 | 2022-10-18 | 南京工业大学 | 一种脂肪酶催化合成色烯类化合物的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2884119B2 (ja) * | 1991-01-29 | 1999-04-19 | メルシャン株式会社 | ベンゼンジカルボン酸モノエステルまたはその誘導体の製造方法 |
| JPH0747562B2 (ja) * | 1993-01-29 | 1995-05-24 | 磐田化学工業株式会社 | ２−メチレングルタール酸１−モノエステルとその製造法 |
| US20040249188A1 (en) * | 2003-05-29 | 2004-12-09 | Dr. Reddy's Laboratories Limited | Process for the preparation of 3-ethoxy-4-(alkoxy carbonyl)-phenyl acetic acid. (an intermediate of repaglinide) |
-
2007
- 2007-01-22 FR FR0752792A patent/FR2911603B1/fr not_active Expired - Fee Related
-
2008
- 2008-01-22 DK DK08761962.3T patent/DK2121950T3/da active
- 2008-01-22 ES ES08761962T patent/ES2363573T3/es active Active
- 2008-01-22 PT PT08761962T patent/PT2121950E/pt unknown
- 2008-01-22 AT AT08761962T patent/ATE504657T1/de active
- 2008-01-22 PL PL08761962T patent/PL2121950T3/pl unknown
- 2008-01-22 DE DE602008006038T patent/DE602008006038D1/de active Active
- 2008-01-22 CN CN2008800028508A patent/CN101652483B/zh active Active
- 2008-01-22 US US12/523,602 patent/US8198054B2/en not_active Expired - Fee Related
- 2008-01-22 EP EP08761962A patent/EP2121950B1/fr active Active
- 2008-01-22 SI SI200830249T patent/SI2121950T1/sl unknown
- 2008-01-22 WO PCT/FR2008/050095 patent/WO2008110706A2/fr active Application Filing
-
2009
- 2009-07-16 IL IL199910A patent/IL199910A/en active IP Right Grant
-
2011
- 2011-07-01 HR HR20110489T patent/HRP20110489T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008110706A2 (fr) | 2008-09-18 |
| ATE504657T1 (de) | 2011-04-15 |
| WO2008110706A3 (fr) | 2008-11-06 |
| DE602008006038D1 (de) | 2011-05-19 |
| US20100068770A1 (en) | 2010-03-18 |
| ES2363573T3 (es) | 2011-08-09 |
| IL199910A (en) | 2011-03-31 |
| CN101652483A (zh) | 2010-02-17 |
| FR2911603B1 (fr) | 2009-04-17 |
| US8198054B2 (en) | 2012-06-12 |
| IL199910A0 (en) | 2010-04-15 |
| EP2121950A2 (fr) | 2009-11-25 |
| PT2121950E (pt) | 2011-07-05 |
| EP2121950B1 (fr) | 2011-04-06 |
| PL2121950T3 (pl) | 2011-09-30 |
| SI2121950T1 (sl) | 2011-08-31 |
| FR2911603A1 (fr) | 2008-07-25 |
| CN101652483B (zh) | 2013-04-10 |
| DK2121950T3 (da) | 2011-07-18 |
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