GB1391088A - Production of d-alpha-amino-1,4-cyclohexadienyl methyl penicillin - Google Patents
Production of d-alpha-amino-1,4-cyclohexadienyl methyl penicillinInfo
- Publication number
- GB1391088A GB1391088A GB3701072A GB3701072A GB1391088A GB 1391088 A GB1391088 A GB 1391088A GB 3701072 A GB3701072 A GB 3701072A GB 3701072 A GB3701072 A GB 3701072A GB 1391088 A GB1391088 A GB 1391088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyclohexadienyl
- amino
- methyl
- epicillin
- aug
- 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
- 229930182555 Penicillin Natural products 0.000 title abstract 2
- 229940049954 penicillin Drugs 0.000 title abstract 2
- 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 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- JBJJTCGQCRGNOL-SSDOTTSWSA-N (2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetic acid Chemical compound OC(=O)[C@H](N)C1=CCC=CC1 JBJJTCGQCRGNOL-SSDOTTSWSA-N 0.000 abstract 2
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 abstract 2
- 229960002457 epicillin Drugs 0.000 abstract 2
- 239000002609 medium Substances 0.000 abstract 2
- 244000005700 microbiome Species 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 241000589565 Flavobacterium Species 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- -1 methyl ester hydrochloride Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
1391088 Preparing epicillin EISAI CO Ltd 8 Aug 1972 [12 Aug 1971] 37010/72 Heading C2C D - α - amino - (1,4 - cyclohexadienyl)methyl penicillin (epicillin) is prepared by reacting 6- aminopenicillanic acid or a salt thereof with an ester (preferably the methyl or ethyl ester) or amide of D-2-amino-2-(1,4-cyclohexadienyl)- acetic acid or an acid addition salt thereof in an aqueous medium in the presence of the microorganism Flavobacterium EF 44-102 Nov. Sp. (ATCC No. 21429), or an enzymatically active medium derived therefrom. The microorganism is aerobically grown on conventional medium and may be used as the culture broth, a cell extract, enzyme preparation, or the separated cells. D - 2 - Amino - 2 - (1,4 - cyclohexadienyl)- acetic acid is prepared by reducing D-phenylglycine with lithium in liquid ammonia. The compound is treeated with thionyl chloride in methanol to convert it to its methyl ester hydrochloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6063671A JPS4826985A (en) | 1971-08-12 | 1971-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1391088A true GB1391088A (en) | 1975-04-16 |
Family
ID=13147985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3701072A Expired GB1391088A (en) | 1971-08-12 | 1972-08-08 | Production of d-alpha-amino-1,4-cyclohexadienyl methyl penicillin |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS4826985A (en) |
| DE (1) | DE2239608A1 (en) |
| FR (1) | FR2148635B1 (en) |
| GB (1) | GB1391088A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2240102A (en) * | 1990-01-22 | 1991-07-24 | Biochemie Gmbh | Beta-lactam production |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW555855B (en) * | 1996-07-26 | 2003-10-01 | Bristol Myers Squibb Co | Synthesis of beta-lactam antibacterials using soluble side chain esters and enzyme acylase |
-
1971
- 1971-08-12 JP JP6063671A patent/JPS4826985A/ja active Pending
-
1972
- 1972-08-08 GB GB3701072A patent/GB1391088A/en not_active Expired
- 1972-08-11 DE DE19722239608 patent/DE2239608A1/en active Pending
- 1972-08-11 FR FR7229173A patent/FR2148635B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2240102A (en) * | 1990-01-22 | 1991-07-24 | Biochemie Gmbh | Beta-lactam production |
| GB2240102B (en) * | 1990-01-22 | 1993-10-20 | Biochemie Gmbh | Improvements in or relating to beta lactam production |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2239608A1 (en) | 1973-02-22 |
| JPS4826985A (en) | 1973-04-09 |
| FR2148635A1 (en) | 1973-03-23 |
| FR2148635B1 (en) | 1975-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |