DE1670033A1 - Verfahren zum Herstellen von halbsynthetischen Penicillinen auf enzymatischem Wege - Google Patents
Verfahren zum Herstellen von halbsynthetischen Penicillinen auf enzymatischem WegeInfo
- Publication number
- DE1670033A1 DE1670033A1 DE19681670033 DE1670033A DE1670033A1 DE 1670033 A1 DE1670033 A1 DE 1670033A1 DE 19681670033 DE19681670033 DE 19681670033 DE 1670033 A DE1670033 A DE 1670033A DE 1670033 A1 DE1670033 A1 DE 1670033A1
- Authority
- DE
- Germany
- Prior art keywords
- penicillin
- group
- acid
- aralkyl
- alkyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 25
- 229930182555 Penicillin Natural products 0.000 title claims description 21
- 230000002255 enzymatic effect Effects 0.000 title claims description 12
- 150000002960 penicillins Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 24
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical group [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 18
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 18
- 229940049954 penicillin Drugs 0.000 claims description 14
- 239000002253 acid Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- -1 Iryl Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 3
- 125000003277 amino group Chemical class 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 16
- 235000010633 broth Nutrition 0.000 description 13
- 102000004190 Enzymes Human genes 0.000 description 10
- 108090000790 Enzymes Proteins 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 6
- 235000019371 penicillin G benzathine Nutrition 0.000 description 5
- 229940056360 penicillin g Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 241001515965 unidentified phage Species 0.000 description 2
- VYCUUOHOBUPEPJ-UHFFFAOYSA-N 2-phenoxybutanamide Chemical compound CCC(C(N)=O)OC1=CC=CC=C1 VYCUUOHOBUPEPJ-UHFFFAOYSA-N 0.000 description 1
- ANCDHBXLDURTHN-UHFFFAOYSA-N 2-phenoxypropanamide Chemical compound NC(=O)C(C)OC1=CC=CC=C1 ANCDHBXLDURTHN-UHFFFAOYSA-N 0.000 description 1
- RCEFMOGVOYEGJN-UHFFFAOYSA-N 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one Chemical compound OC1=CC=CC=C1N1C(=O)NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CC1 RCEFMOGVOYEGJN-UHFFFAOYSA-N 0.000 description 1
- QWMOVJWPTZATFS-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2-oxazol-4-amine Chemical compound NC1=C(C)ON=C1C1=CC=CC=C1 QWMOVJWPTZATFS-UHFFFAOYSA-N 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 229930195708 Penicillin V Natural products 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1345367 | 1967-03-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1670033A1 true DE1670033A1 (de) | 1971-02-25 |
Family
ID=11144456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681670033 Pending DE1670033A1 (de) | 1967-03-08 | 1968-03-02 | Verfahren zum Herstellen von halbsynthetischen Penicillinen auf enzymatischem Wege |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE720791A (enrdf_load_stackoverflow) |
| DE (1) | DE1670033A1 (enrdf_load_stackoverflow) |
| DK (1) | DK132631C (enrdf_load_stackoverflow) |
| FR (1) | FR1574713A (enrdf_load_stackoverflow) |
| GB (1) | GB1213492A (enrdf_load_stackoverflow) |
| NL (1) | NL6705788A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5011475B1 (enrdf_load_stackoverflow) * | 1969-10-16 | 1975-05-01 |
-
1967
- 1967-04-25 NL NL6705788A patent/NL6705788A/xx unknown
-
1968
- 1968-02-08 FR FR1574713D patent/FR1574713A/fr not_active Expired
- 1968-03-02 DE DE19681670033 patent/DE1670033A1/de active Pending
- 1968-03-07 DK DK95368A patent/DK132631C/da active
- 1968-03-08 GB GB1155168A patent/GB1213492A/en not_active Expired
- 1968-09-13 BE BE720791D patent/BE720791A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1574713A (enrdf_load_stackoverflow) | 1969-07-18 |
| NL6705788A (enrdf_load_stackoverflow) | 1968-09-09 |
| DK132631B (da) | 1976-01-12 |
| DK132631C (da) | 1976-06-08 |
| GB1213492A (en) | 1970-11-25 |
| BE720791A (enrdf_load_stackoverflow) | 1969-02-17 |
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