DD282918A5 - Enzymatisches verfahren zur herstellung von peptiden, insbesondere dipeptiden und vorrichtung dafuer - Google Patents
Enzymatisches verfahren zur herstellung von peptiden, insbesondere dipeptiden und vorrichtung dafuer Download PDFInfo
- Publication number
- DD282918A5 DD282918A5 DD88320269A DD32026988A DD282918A5 DD 282918 A5 DD282918 A5 DD 282918A5 DD 88320269 A DD88320269 A DD 88320269A DD 32026988 A DD32026988 A DD 32026988A DD 282918 A5 DD282918 A5 DD 282918A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- amino acid
- protected
- reaction
- peptide
- enzyme
- Prior art date
Links
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 30
- 108010016626 Dipeptides Proteins 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000002255 enzymatic effect Effects 0.000 title claims abstract description 12
- 102000004196 processed proteins & peptides Human genes 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 230000008569 process Effects 0.000 title claims abstract description 6
- 108090000790 Enzymes Proteins 0.000 claims abstract description 32
- 102000004190 Enzymes Human genes 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 150000001413 amino acids Chemical class 0.000 claims abstract description 17
- -1 N-protected amino Chemical group 0.000 claims abstract description 15
- 239000012528 membrane Substances 0.000 claims abstract description 13
- 125000006239 protecting group Chemical group 0.000 claims abstract description 13
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 10
- 108010073038 Penicillin Amidase Proteins 0.000 claims abstract description 8
- 238000001179 sorption measurement Methods 0.000 claims abstract description 8
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 6
- 239000008346 aqueous phase Substances 0.000 claims abstract description 5
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 5
- 238000010647 peptide synthesis reaction Methods 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 102000005367 Carboxypeptidases Human genes 0.000 claims abstract description 3
- 108010006303 Carboxypeptidases Proteins 0.000 claims abstract description 3
- 102000035195 Peptidases Human genes 0.000 claims abstract description 3
- 108091005804 Peptidases Proteins 0.000 claims abstract description 3
- 102000012479 Serine Proteases Human genes 0.000 claims abstract description 3
- 108010022999 Serine Proteases Proteins 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims abstract description 3
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 3
- 230000007717 exclusion Effects 0.000 claims abstract description 3
- 235000019833 protease Nutrition 0.000 claims abstract description 3
- 235000001014 amino acid Nutrition 0.000 claims description 27
- 229940024606 amino acid Drugs 0.000 claims description 27
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 10
- 235000004279 alanine Nutrition 0.000 claims description 10
- 229920001429 chelating resin Polymers 0.000 claims description 8
- 238000003776 cleavage reaction Methods 0.000 claims description 7
- 230000007017 scission Effects 0.000 claims description 7
- 230000020176 deacylation Effects 0.000 claims description 5
- 238000005947 deacylation reaction Methods 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 230000000717 retained effect Effects 0.000 claims description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960000310 isoleucine Drugs 0.000 claims description 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 2
- 229930182817 methionine Natural products 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- NLKUJNGEGZDXGO-XVKPBYJWSA-N Tyr-Ala Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 NLKUJNGEGZDXGO-XVKPBYJWSA-N 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 235000016236 parenteral nutrition Nutrition 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000014759 maintenance of location Effects 0.000 abstract 1
- 235000016709 nutrition Nutrition 0.000 abstract 1
- 230000035764 nutrition Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 4
- 108010038807 Oligopeptides Proteins 0.000 description 4
- 102000015636 Oligopeptides Human genes 0.000 description 4
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 102000005572 Cathepsin A Human genes 0.000 description 1
- 108010059081 Cathepsin A Proteins 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- GSYTVXOARWSQSV-BYPYZUCNSA-N L-methioninamide Chemical compound CSCC[C@H](N)C(N)=O GSYTVXOARWSQSV-BYPYZUCNSA-N 0.000 description 1
- LCPYQJIKPJDLLB-UWVGGRQHSA-N Leu-Leu Chemical compound CC(C)C[C@H](N)C(=O)N[C@H](C(O)=O)CC(C)C LCPYQJIKPJDLLB-UWVGGRQHSA-N 0.000 description 1
- 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 description 1
- JXNRXNCCROJZFB-RYUDHWBXSA-N Tyr-Arg Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 JXNRXNCCROJZFB-RYUDHWBXSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002086 displacement chromatography Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 108010053037 kyotorphin Proteins 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
- C07K1/20—Partition-, reverse-phase or hydrophobic interaction chromatography
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/803—Physical recovery methods, e.g. chromatography, grinding
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/813—Continuous fermentation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873733198 DE3733198A1 (de) | 1987-10-01 | 1987-10-01 | Enzymatisches verfahren zur herstellung von dipeptiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD282918A5 true DD282918A5 (de) | 1990-09-26 |
Family
ID=6337394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD88320269A DD282918A5 (de) | 1987-10-01 | 1988-09-29 | Enzymatisches verfahren zur herstellung von peptiden, insbesondere dipeptiden und vorrichtung dafuer |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5057415A (da) |
| EP (1) | EP0309983A3 (da) |
| JP (1) | JPH01222795A (da) |
| DD (1) | DD282918A5 (da) |
| DE (1) | DE3733198A1 (da) |
| DK (1) | DK549688A (da) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4014564C1 (da) * | 1990-05-07 | 1991-07-18 | Forschungszentrum Juelich Gmbh, 5170 Juelich, De | |
| DE4101895C1 (da) * | 1991-01-23 | 1991-12-05 | Forschungszentrum Juelich Gmbh, 5170 Juelich, De | |
| US5874532A (en) * | 1997-01-08 | 1999-02-23 | Nexstar Pharmaceuticals, Inc. | Method for solution phase synthesis of oligonucleotides and peptides |
| JPH11171895A (ja) * | 1997-12-11 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の分離精製方法 |
| US20030032083A1 (en) * | 2001-05-23 | 2003-02-13 | Diversa Corporation | Peptide synthesis method |
| US20120282652A1 (en) * | 2011-02-28 | 2012-11-08 | Polytechnic Institute Of New York University | Preparation of peptide mixtures by protease catalysis designed to provide useful biological and physical properties |
| EP2813512B1 (en) | 2011-12-28 | 2021-03-31 | Chugai Seiyaku Kabushiki Kaisha | Peptide-compound cyclization method |
| DK3269809T3 (da) | 2015-03-13 | 2022-09-12 | Chugai Pharmaceutical Co Ltd | MODIFICERET AMINOACYL-tRNA-SYNTETASE OG ANVENDELSE DERAF |
| US12391971B2 (en) | 2017-01-31 | 2025-08-19 | Chugai Seiyaku Kabushiki Kaisha | Method for synthesizing peptides in cell-free translation system |
| KR102744693B1 (ko) | 2017-06-09 | 2024-12-18 | 추가이 세이야쿠 가부시키가이샤 | N-치환 아미노산을 포함하는 펩타이드의 합성 방법 |
| CN111479819B (zh) | 2017-12-15 | 2024-06-14 | 中外制药株式会社 | 制备肽的方法和处理碱的方法 |
| EP3878836B1 (en) | 2018-11-07 | 2025-07-23 | Chugai Seiyaku Kabushiki Kaisha | O-substituted serine derivative production method |
| CN113056475B (zh) | 2018-11-30 | 2024-09-24 | 中外制药株式会社 | 用于肽化合物或酰胺化合物的脱保护方法和在固相反应中的树脂脱除方法以及用于生产肽化合物的方法 |
| US12071396B2 (en) | 2019-03-15 | 2024-08-27 | Chugai Seiyaku Kabushiki Kaisha | Method for preparing aromatic amino acid derivative |
| SG10202111127YA (en) | 2019-11-07 | 2021-11-29 | Chugai Pharmaceutical Co Ltd | Cyclic Peptide Compound Having Kras Inhibitory Action |
| DE102021108406A1 (de) * | 2021-04-01 | 2022-10-06 | Jacobs University Bremen Ggmbh | Vorrichtung und Verfahren zum Abtrennen von in einer Trägerflüssigkeit aufgenommenen Proteinen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA801929B (en) * | 1979-04-06 | 1981-11-25 | Forenede Bryggerier As | A process for enzymatic production of peptides |
| DE2930070A1 (de) * | 1979-07-25 | 1981-02-19 | Biotechnolog Forschung Gmbh | Verfahren zur kontinuierlichen enzymatischen umwandlung von wasserloeslichen alpha -ketocarbonsaeuren in die entsprechenden aminosaeuren |
| DE2930087A1 (de) * | 1979-07-25 | 1981-02-26 | Biotechnolog Forschung Gmbh | Verfahren zur kontinuierlichen enzymatischen umwandlung von wasserloeslichen alpha -ketocarbonsaeuren in die entsprechenden alpha -hydroxycarbonsaeuren |
| DK72587D0 (da) * | 1987-02-13 | 1987-02-13 | Carlsberg Biotechnology Ltd | Fremgangsmaade til enzymatisk fremstilling af dipeptider |
-
1987
- 1987-10-01 DE DE19873733198 patent/DE3733198A1/de not_active Withdrawn
-
1988
- 1988-09-27 EP EP19880115873 patent/EP0309983A3/de not_active Withdrawn
- 1988-09-29 JP JP63242646A patent/JPH01222795A/ja active Pending
- 1988-09-29 DD DD88320269A patent/DD282918A5/de not_active IP Right Cessation
- 1988-09-30 DK DK549688A patent/DK549688A/da not_active Application Discontinuation
- 1988-09-30 US US07/251,176 patent/US5057415A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DK549688D0 (da) | 1988-09-30 |
| DK549688A (da) | 1989-04-02 |
| JPH01222795A (ja) | 1989-09-06 |
| US5057415A (en) | 1991-10-15 |
| EP0309983A2 (de) | 1989-04-05 |
| EP0309983A3 (de) | 1991-03-27 |
| DE3733198A1 (de) | 1989-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |