CH575355A5 - Resolution of 3-fluoro dl-alanine - by selective enzymic hydrolysis of the n-chloroacetyl derivs - Google Patents
Resolution of 3-fluoro dl-alanine - by selective enzymic hydrolysis of the n-chloroacetyl derivsInfo
- Publication number
- CH575355A5 CH575355A5 CH148673A CH148673A CH575355A5 CH 575355 A5 CH575355 A5 CH 575355A5 CH 148673 A CH148673 A CH 148673A CH 148673 A CH148673 A CH 148673A CH 575355 A5 CH575355 A5 CH 575355A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alanine
- fluoro
- chloroacetyl
- deutero
- optionally
- Prior art date
Links
- 230000007062 hydrolysis Effects 0.000 title claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 title claims description 5
- UYTSRQMXRROFPU-UHFFFAOYSA-N 2-azaniumyl-3-fluoropropanoate Chemical compound FCC(N)C(O)=O UYTSRQMXRROFPU-UHFFFAOYSA-N 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- UYTSRQMXRROFPU-REOHCLBHSA-N (2r)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@H](N)C(O)=O UYTSRQMXRROFPU-REOHCLBHSA-N 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 8
- ULOVGZHDGRVJBG-UHFFFAOYSA-N 2-[(2-chloroacetyl)amino]-3-fluoropropanoic acid Chemical compound ClCC(=O)NC(CF)C(=O)O ULOVGZHDGRVJBG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000001640 fractional crystallisation Methods 0.000 claims abstract description 5
- 108010003977 aminoacylase I Proteins 0.000 claims abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- ULOVGZHDGRVJBG-GSVOUGTGSA-N (2S)-2-[(2-chloroacetyl)amino]-3-fluoropropanoic acid Chemical compound ClCC(=O)N[C@H](CF)C(=O)O ULOVGZHDGRVJBG-GSVOUGTGSA-N 0.000 claims description 8
- UYTSRQMXRROFPU-UWTATZPHSA-N (2s)-2-amino-3-fluoropropanoic acid Chemical compound FC[C@@H](N)C(O)=O UYTSRQMXRROFPU-UWTATZPHSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 230000002255 enzymatic effect Effects 0.000 claims description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000006196 deacetylation Effects 0.000 claims description 4
- 238000003381 deacetylation reaction Methods 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- DHALQLNIDMSKHU-UHFFFAOYSA-N 2-(fluoroamino)propanoic acid Chemical compound FNC(C)C(O)=O DHALQLNIDMSKHU-UHFFFAOYSA-N 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- -1 N-chloroacetyl-2-deutero-3-fluoro-DL-alanine Chemical compound 0.000 claims description 2
- 229940024606 amino acid Drugs 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 244000052616 bacterial pathogen Species 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 230000029087 digestion Effects 0.000 claims description 2
- 229950010030 dl-alanine Drugs 0.000 claims description 2
- 238000006911 enzymatic reaction Methods 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
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)
- Enzymes And Modification Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22329372A | 1972-02-03 | 1972-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH575355A5 true CH575355A5 (en) | 1976-05-14 |
Family
ID=22835886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH148673A CH575355A5 (en) | 1972-02-03 | 1973-02-02 | Resolution of 3-fluoro dl-alanine - by selective enzymic hydrolysis of the n-chloroacetyl derivs |
Country Status (9)
-
1973
- 1973-01-15 NL NL7300578A patent/NL7300578A/xx unknown
- 1973-01-22 CS CS47673A patent/CS171275B2/cs unknown
- 1973-01-27 PL PL16043473A patent/PL84477B1/pl unknown
- 1973-01-30 AT AT79373A patent/AT317123B/de not_active IP Right Cessation
- 1973-01-31 ES ES411141A patent/ES411141A1/es not_active Expired
- 1973-02-01 DD DD16861173A patent/DD106164A5/xx unknown
- 1973-02-01 SU SU1878073A patent/SU484683A3/ru active
- 1973-02-02 CH CH148673A patent/CH575355A5/de not_active IP Right Cessation
- 1973-02-02 JP JP1302573A patent/JPS4885789A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AT317123B (de) | 1974-08-12 |
| JPS4885789A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-13 |
| ES411141A1 (es) | 1975-12-01 |
| SU484683A3 (ru) | 1975-09-15 |
| PL84477B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-04-30 |
| CS171275B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-10-29 |
| NL7300578A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-08-07 |
| DD106164A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |