NO821585L - Fremgangsmaate ved fjerning av formylgruppen fra n-formylpeptider og estere derav - Google Patents
Fremgangsmaate ved fjerning av formylgruppen fra n-formylpeptider og estere deravInfo
- Publication number
- NO821585L NO821585L NO821585A NO821585A NO821585L NO 821585 L NO821585 L NO 821585L NO 821585 A NO821585 A NO 821585A NO 821585 A NO821585 A NO 821585A NO 821585 L NO821585 L NO 821585L
- Authority
- NO
- Norway
- Prior art keywords
- reaction
- compound
- peptide
- group
- hydrazine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical group OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 claims description 27
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 19
- 108010011485 Aspartame Proteins 0.000 claims description 16
- 229960003438 aspartame Drugs 0.000 claims description 16
- 235000010357 aspartame Nutrition 0.000 claims description 16
- 239000000605 aspartame Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 150000002429 hydrazines Chemical class 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 108010008211 N-Formylmethionine Leucyl-Phenylalanine Proteins 0.000 claims description 3
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 17
- 238000006344 deformylation reaction Methods 0.000 description 15
- 102000004196 processed proteins & peptides Human genes 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 230000006198 deformylation Effects 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- BXRNXXXXHLBUKK-UHFFFAOYSA-N piperazine-2,5-dione Chemical compound O=C1CNC(=O)CN1 BXRNXXXXHLBUKK-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- OSEHTEQTVJQGDE-RYUDHWBXSA-N (3s)-3-formamido-4-[[(2s)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 OSEHTEQTVJQGDE-RYUDHWBXSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- VNHJXYUDIBQDDX-UHFFFAOYSA-N L-cis-Cyclo(aspartylphenylalanyl) Chemical compound N1C(=O)C(CC(=O)O)NC(=O)C1CC1=CC=CC=C1 VNHJXYUDIBQDDX-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- -1 acetyl- Chemical group 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- WYYUBJAMROQJSF-QWRGUYRKSA-N (3s)-4-[[(1s)-1-carboxy-2-phenylethyl]amino]-3-formamido-4-oxobutanoic acid Chemical compound OC(=O)C[C@H](NC=O)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 WYYUBJAMROQJSF-QWRGUYRKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- YZQCXOFQZKCETR-UWVGGRQHSA-N Asp-Phe Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 YZQCXOFQZKCETR-UWVGGRQHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- MQUUQXIFCBBFDP-VKHMYHEASA-N N-formyl-L-aspartic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC=O MQUUQXIFCBBFDP-VKHMYHEASA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 231100000167 toxic agent Toxicity 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
-
- 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
- C07K1/12—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by hydrolysis, i.e. solvolysis in general
- C07K1/124—Hydrazinolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Analytical Chemistry (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21674/81A IT1194795B (it) | 1981-05-13 | 1981-05-13 | Procedimento per la eliminazione del gruppo n-formile da peptidi n-formilati e da esteri di peptidi n-formilati |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO821585L true NO821585L (no) | 1982-11-15 |
Family
ID=11185195
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821585A NO821585L (no) | 1981-05-13 | 1982-05-12 | Fremgangsmaate ved fjerning av formylgruppen fra n-formylpeptider og estere derav |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4434097A (fr) |
| JP (1) | JPS5810546A (fr) |
| KR (1) | KR840001342B1 (fr) |
| AT (1) | ATA183082A (fr) |
| AU (1) | AU537275B2 (fr) |
| BE (1) | BE893074A (fr) |
| CA (1) | CA1244406A (fr) |
| CH (1) | CH648566A5 (fr) |
| DE (1) | DE3216512C2 (fr) |
| DK (1) | DK208082A (fr) |
| ES (1) | ES8302633A1 (fr) |
| FI (1) | FI821412L (fr) |
| FR (1) | FR2505829B1 (fr) |
| GB (1) | GB2098220B (fr) |
| GR (1) | GR75497B (fr) |
| IT (1) | IT1194795B (fr) |
| NL (1) | NL8201821A (fr) |
| NO (1) | NO821585L (fr) |
| NZ (1) | NZ200583A (fr) |
| PT (1) | PT74892B (fr) |
| SE (1) | SE8202787L (fr) |
| YU (1) | YU93882A (fr) |
| ZA (1) | ZA823232B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4555362A (en) * | 1983-06-20 | 1985-11-26 | G. D. Searle & Co. | Method and intermediates for producing α-L-aspartyl-L-phenylalanine |
| IT1190395B (it) * | 1985-09-30 | 1988-02-16 | Lark Spa | Procedimento per la rimozione del gruppo formile da un estere di n-formil peptide o di n-formil amminoacido |
| ATE487486T1 (de) * | 2002-05-24 | 2010-11-15 | Medtronic Inc | Polypeptid-spaltungsprozess |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1543610A1 (de) * | 1966-08-27 | 1969-07-31 | Hoechst Ag | Verfahren zur Herstellung von Aminosaeuren und Peptiden und deren Derivaten |
| US3933781A (en) * | 1973-11-05 | 1976-01-20 | Monsanto Company | Process for the preparation of α-L-aspartyl-L-phenylalanine alkyl esters |
| JPS5823380B2 (ja) * | 1974-12-05 | 1983-05-14 | 味の素株式会社 | ホルミルキノ ダツリホウ |
| JPS5223001A (en) * | 1975-08-14 | 1977-02-21 | Ajinomoto Co Inc | Process for elimination of formyl group |
-
1981
- 1981-05-13 IT IT21674/81A patent/IT1194795B/it active
-
1982
- 1982-04-23 FI FI821412A patent/FI821412L/fi not_active Application Discontinuation
- 1982-04-26 US US06/372,216 patent/US4434097A/en not_active Expired - Fee Related
- 1982-04-28 ES ES511760A patent/ES8302633A1/es not_active Expired
- 1982-04-29 YU YU00938/82A patent/YU93882A/xx unknown
- 1982-04-30 CA CA000402109A patent/CA1244406A/fr not_active Expired
- 1982-04-30 CH CH2642/82A patent/CH648566A5/it not_active IP Right Cessation
- 1982-05-03 NL NL8201821A patent/NL8201821A/nl not_active Application Discontinuation
- 1982-05-03 DE DE3216512A patent/DE3216512C2/de not_active Expired
- 1982-05-04 SE SE8202787A patent/SE8202787L/ not_active Application Discontinuation
- 1982-05-05 BE BE2/59692A patent/BE893074A/fr not_active IP Right Cessation
- 1982-05-07 GB GB8213232A patent/GB2098220B/en not_active Expired
- 1982-05-10 AT AT0183082A patent/ATA183082A/de not_active Application Discontinuation
- 1982-05-10 DK DK208082A patent/DK208082A/da unknown
- 1982-05-11 JP JP57079805A patent/JPS5810546A/ja active Granted
- 1982-05-11 ZA ZA823232A patent/ZA823232B/xx unknown
- 1982-05-11 NZ NZ200583A patent/NZ200583A/en unknown
- 1982-05-12 NO NO821585A patent/NO821585L/no unknown
- 1982-05-12 PT PT74892A patent/PT74892B/pt unknown
- 1982-05-12 AU AU83612/82A patent/AU537275B2/en not_active Ceased
- 1982-05-13 GR GR68142A patent/GR75497B/el unknown
- 1982-05-13 KR KR8202080A patent/KR840001342B1/ko not_active IP Right Cessation
- 1982-05-13 FR FR8208355A patent/FR2505829B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI821412A0 (fi) | 1982-04-23 |
| FI821412L (fi) | 1982-11-14 |
| DE3216512A1 (de) | 1982-12-23 |
| YU93882A (en) | 1985-08-31 |
| GB2098220B (en) | 1984-08-15 |
| ATA183082A (de) | 1989-04-15 |
| PT74892A (en) | 1982-06-01 |
| KR830010053A (ko) | 1983-12-24 |
| SE8202787L (sv) | 1982-11-14 |
| IT1194795B (it) | 1988-09-28 |
| CH648566A5 (it) | 1985-03-29 |
| GR75497B (fr) | 1984-07-24 |
| PT74892B (en) | 1984-08-02 |
| NL8201821A (nl) | 1982-12-01 |
| US4434097A (en) | 1984-02-28 |
| DE3216512C2 (de) | 1986-09-11 |
| CA1244406A (fr) | 1988-11-08 |
| BE893074A (fr) | 1982-08-30 |
| IT8121674A1 (it) | 1982-11-13 |
| KR840001342B1 (ko) | 1984-09-19 |
| JPS5810546A (ja) | 1983-01-21 |
| AU8361282A (en) | 1982-11-18 |
| JPS616080B2 (fr) | 1986-02-24 |
| ES511760A0 (es) | 1983-02-01 |
| ZA823232B (en) | 1983-03-30 |
| FR2505829B1 (fr) | 1985-10-25 |
| ES8302633A1 (es) | 1983-02-01 |
| IT8121674A0 (it) | 1981-05-13 |
| DK208082A (da) | 1982-11-14 |
| AU537275B2 (en) | 1984-06-14 |
| FR2505829A1 (fr) | 1982-11-19 |
| GB2098220A (en) | 1982-11-17 |
| NZ200583A (en) | 1984-12-14 |
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