FR2188608A5 - Penicillins prepn by acylating 6-apa - in presence of catalytic enzymes using free acids - Google Patents
Penicillins prepn by acylating 6-apa - in presence of catalytic enzymes using free acidsInfo
- Publication number
- FR2188608A5 FR2188608A5 FR7221319A FR7221319A FR2188608A5 FR 2188608 A5 FR2188608 A5 FR 2188608A5 FR 7221319 A FR7221319 A FR 7221319A FR 7221319 A FR7221319 A FR 7221319A FR 2188608 A5 FR2188608 A5 FR 2188608A5
- Authority
- FR
- France
- Prior art keywords
- apa
- penicillins
- prepn
- acylating
- free acids
- 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.)
- Expired
Links
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title abstract 3
- 102000004190 Enzymes Human genes 0.000 title abstract 2
- 108090000790 Enzymes Proteins 0.000 title abstract 2
- 229930182555 Penicillin Natural products 0.000 title abstract 2
- 230000003197 catalytic effect Effects 0.000 title abstract 2
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 4
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000000034 method 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
- C12P37/00—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin
- C12P37/04—Preparation of compounds having a 4-thia-1-azabicyclo [3.2.0] heptane ring system, e.g. penicillin by acylation of the substituent in the 6 position
Landscapes
- 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)
Abstract
Penicillins of formula: R.CH.CO- 6-APA (where R is opt. substd) benzyl and 6-APA is 6-aminopenicillanic acid are prepd by acylation of 6-APA in presence of a catalytic enzyme, using the acid R-CH(NH2)CO2H, instead of the acid halides or anhydrides of known processes, high yields are obtd.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7221319A FR2188608A5 (en) | 1972-06-14 | 1972-06-14 | Penicillins prepn by acylating 6-apa - in presence of catalytic enzymes using free acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7221319A FR2188608A5 (en) | 1972-06-14 | 1972-06-14 | Penicillins prepn by acylating 6-apa - in presence of catalytic enzymes using free acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2188608A5 true FR2188608A5 (en) | 1974-01-18 |
Family
ID=9100165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7221319A Expired FR2188608A5 (en) | 1972-06-14 | 1972-06-14 | Penicillins prepn by acylating 6-apa - in presence of catalytic enzymes using free acids |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2188608A5 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991009136A1 (en) * | 1989-12-12 | 1991-06-27 | Consejo Superior Investigaciones Cientificas | Method for the synthesis of semi-synthetic antibiotics in thermodynamically controlled water-cosolvent organic miscible apolar systems by using penicillin g acylase |
| WO1996030376A1 (en) * | 1995-03-31 | 1996-10-03 | Chemferm V.O.F. | Process for the recovery of ampicillin |
| NL1006266C2 (en) * | 1997-06-10 | 1998-12-14 | Chemferm Vof | Method for the preparation of ampicillin. |
-
1972
- 1972-06-14 FR FR7221319A patent/FR2188608A5/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991009136A1 (en) * | 1989-12-12 | 1991-06-27 | Consejo Superior Investigaciones Cientificas | Method for the synthesis of semi-synthetic antibiotics in thermodynamically controlled water-cosolvent organic miscible apolar systems by using penicillin g acylase |
| US5268271A (en) * | 1989-12-12 | 1993-12-07 | Cosejo Superior De Invetigaciones Certificas | Method for the synthesis of semi-synthetic antibiotics in thermodynamically controlled water-cosolvent organic miscible apolar systems by using penicillin G acylase |
| WO1996030376A1 (en) * | 1995-03-31 | 1996-10-03 | Chemferm V.O.F. | Process for the recovery of ampicillin |
| BE1009264A3 (en) * | 1995-03-31 | 1997-01-07 | Dsm Nv | Process for the extraction of ampicillin. |
| CN1103777C (en) * | 1995-03-31 | 2003-03-26 | Dsm有限公司 | Recovery of ampicillin |
| NL1006266C2 (en) * | 1997-06-10 | 1998-12-14 | Chemferm Vof | Method for the preparation of ampicillin. |
| WO1998056946A1 (en) * | 1997-06-10 | 1998-12-17 | Dsm N.V. | Process for the preparation of ampicillin |
| US7029885B2 (en) | 1997-06-10 | 2006-04-18 | Dsm Ip Assests B.V. | Process for the preparation of ampicillin |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |