BRPI0202783B1 - processo para a síntese rápida de um peptídeo em solução em um solvente orgânico ou em uma mistura de solventes orgânicos, e, métodos para a síntese combinatória de coleções de peptídeo e para a síntese de peptídeo automatizada em solução - Google Patents
processo para a síntese rápida de um peptídeo em solução em um solvente orgânico ou em uma mistura de solventes orgânicos, e, métodos para a síntese combinatória de coleções de peptídeo e para a síntese de peptídeo automatizada em solução Download PDFInfo
- Publication number
- BRPI0202783B1 BRPI0202783B1 BRPI0202783A BR0202783A BRPI0202783B1 BR PI0202783 B1 BRPI0202783 B1 BR PI0202783B1 BR PI0202783 A BRPI0202783 A BR PI0202783A BR 0202783 A BR0202783 A BR 0202783A BR PI0202783 B1 BRPI0202783 B1 BR PI0202783B1
- Authority
- BR
- Brazil
- Prior art keywords
- process according
- peptide
- remover
- synthesis
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 92
- 230000008569 process Effects 0.000 title claims abstract description 76
- 108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 46
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 239000003960 organic solvent Substances 0.000 title claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 13
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 13
- 238000010647 peptide synthesis reaction Methods 0.000 title claims abstract description 7
- 238000000605 extraction Methods 0.000 claims abstract description 28
- 238000005859 coupling reaction Methods 0.000 claims abstract description 24
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 24
- 150000001450 anions Chemical class 0.000 claims abstract description 22
- 230000008878 coupling Effects 0.000 claims abstract description 22
- 238000010168 coupling process Methods 0.000 claims abstract description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000003252 repetitive effect Effects 0.000 claims abstract description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 239000011780 sodium chloride Substances 0.000 claims description 36
- 125000006239 protecting group Chemical group 0.000 claims description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims description 14
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 229920000768 polyamine Polymers 0.000 claims description 9
- CANCPUBPPUIWPX-UHFFFAOYSA-N benzyl 3-aminopropanoate Chemical group NCCC(=O)OCC1=CC=CC=C1 CANCPUBPPUIWPX-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 7
- 239000004323 potassium nitrate Substances 0.000 claims description 7
- 235000010333 potassium nitrate Nutrition 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 150000003141 primary amines Chemical group 0.000 claims description 3
- 238000010791 quenching Methods 0.000 claims description 3
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 2
- 229940000635 beta-alanine Drugs 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract description 11
- 102000015636 Oligopeptides Human genes 0.000 abstract description 6
- 108010038807 Oligopeptides Proteins 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 229920001184 polypeptide Polymers 0.000 abstract description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 19
- -1 thiophen-2-yl-methoxycarbonyl Chemical group 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 11
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
- 238000007327 hydrogenolysis reaction Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000013459 approach Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 108010016626 Dipeptides Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000002516 radical scavenger Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- XYXYXSKSTZAEJW-VIFPVBQESA-N (2s)-2-(phenylmethoxycarbonylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 XYXYXSKSTZAEJW-VIFPVBQESA-N 0.000 description 2
- MCRMUCXATQAAMN-HNNXBMFYSA-N (2s)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=C(O)C=C1 MCRMUCXATQAAMN-HNNXBMFYSA-N 0.000 description 2
- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 2
- TZCYLJGNWDVJRA-UHFFFAOYSA-N 6-chloro-1-hydroxybenzotriazole Chemical compound C1=C(Cl)C=C2N(O)N=NC2=C1 TZCYLJGNWDVJRA-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000012217 deletion Methods 0.000 description 2
- 230000037430 deletion Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000004007 reversed phase HPLC Methods 0.000 description 2
- 238000013341 scale-up Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- DYWUPCCKOVTCFZ-LBPRGKRZSA-N (2s)-2-amino-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=C(C[C@H](N)C(O)=O)C2=C1 DYWUPCCKOVTCFZ-LBPRGKRZSA-N 0.000 description 1
- WCOJOHPAKJFUDF-LBPRGKRZSA-N (2s)-3-(1h-imidazol-5-yl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CN=CN1 WCOJOHPAKJFUDF-LBPRGKRZSA-N 0.000 description 1
- AHYFYYVVAXRMKB-KRWDZBQOSA-N (2s)-3-(1h-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)OCC1=CC=CC=C1 AHYFYYVVAXRMKB-KRWDZBQOSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- HJBLUNHMOKFZQX-UHFFFAOYSA-N 3-hydroxy-1,2,3-benzotriazin-4-one Chemical compound C1=CC=C2C(=O)N(O)N=NC2=C1 HJBLUNHMOKFZQX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- USPFMEKVPDBMCG-LBPRGKRZSA-N N-benzyloxycarbonyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 USPFMEKVPDBMCG-LBPRGKRZSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 150000002433 hydrophilic molecules Chemical class 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005500 uronium group Chemical group 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
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01202753 | 2001-07-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR0202783A BR0202783A (pt) | 2003-06-10 |
| BRPI0202783B1 true BRPI0202783B1 (pt) | 2016-07-05 |
Family
ID=8180656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0202783A BRPI0202783B1 (pt) | 2001-07-19 | 2002-07-18 | processo para a síntese rápida de um peptídeo em solução em um solvente orgânico ou em uma mistura de solventes orgânicos, e, métodos para a síntese combinatória de coleções de peptídeo e para a síntese de peptídeo automatizada em solução |
Country Status (25)
| Country | Link |
|---|---|
| US (4) | US20030018164A1 (OSRAM) |
| EP (1) | EP1291356B1 (OSRAM) |
| JP (1) | JP4142907B2 (OSRAM) |
| KR (1) | KR100861031B1 (OSRAM) |
| CN (1) | CN1254483C (OSRAM) |
| AR (1) | AR034869A1 (OSRAM) |
| AT (1) | ATE302792T1 (OSRAM) |
| BR (1) | BRPI0202783B1 (OSRAM) |
| CA (1) | CA2390358C (OSRAM) |
| DE (1) | DE60205693T2 (OSRAM) |
| DK (1) | DK1291356T3 (OSRAM) |
| EC (1) | ECSP024291A (OSRAM) |
| ES (1) | ES2248485T3 (OSRAM) |
| HR (1) | HRP20020609B1 (OSRAM) |
| HU (1) | HUP0202369A2 (OSRAM) |
| IL (1) | IL150601A (OSRAM) |
| MX (1) | MXPA02006998A (OSRAM) |
| NO (1) | NO324245B1 (OSRAM) |
| PE (1) | PE20030214A1 (OSRAM) |
| PL (1) | PL205559B1 (OSRAM) |
| PT (1) | PT1291356E (OSRAM) |
| RU (1) | RU2237673C2 (OSRAM) |
| SG (1) | SG119160A1 (OSRAM) |
| TW (1) | TWI247012B (OSRAM) |
| ZA (1) | ZA200205409B (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL150601A (en) * | 2001-07-19 | 2010-06-30 | Organon Nv | Process for rapid synthesis of peptides within a solution using the back of an activated carboxyl component and destruction of the residual activated carboxyl component |
| EP1790656A1 (en) * | 2005-11-25 | 2007-05-30 | Nanokem S.A. | Solution-phase synthesis of leuprolide |
| EP1801086A1 (en) * | 2005-11-25 | 2007-06-27 | Synthacon GmbH | Synthesis of carbon acid amides |
| DE602007005349D1 (de) * | 2006-01-17 | 2010-04-29 | Organon Nv | SELEKTIVE ENZYMATISCHE HYDROLYSE VON C-TERMINALEN tert-BUTYL-PEPTIDESTERN |
| JP5171613B2 (ja) * | 2006-03-01 | 2013-03-27 | 株式会社カネカ | ペプチドの製造方法 |
| US8124372B2 (en) | 2007-06-25 | 2012-02-28 | N.V. Organon | Selective enzymatic amidation of C-terminal esters or acids of peptides |
| MX2009013623A (es) * | 2007-06-25 | 2010-01-20 | Organon Nv | Proceso para la conversion de esteres o acidos de peptido de terminal c, a amidas que emplean subtilisina en la presencia de sales de amonio. |
| CA2753224C (en) * | 2008-12-30 | 2018-04-17 | Gkl-Biotec Ag | Peptide combination |
| KR101032399B1 (ko) * | 2010-02-11 | 2011-05-03 | 주식회사 이너트론 | 밴드패스필터의 철재하우징 및 그 제조방법 |
| EP2409982A3 (en) * | 2010-02-25 | 2012-02-08 | Corning Incorporated | Chemical processes generating solid(s) carried out continuously within microreactors |
| WO2013089241A1 (ja) | 2011-12-15 | 2013-06-20 | 味の素株式会社 | Ｆｍｏｃ基の除去方法 |
| CN107406480B (zh) | 2015-03-04 | 2022-06-24 | Jitsubo株式会社 | 肽合成方法 |
| KR102337328B1 (ko) | 2015-12-21 | 2021-12-10 | 텍사스 테크 유니버시티 시스템 | 용액상 gap 펩타이드 합성을 위한 시스템 및 방법 |
| CN111971293B (zh) | 2018-04-13 | 2024-07-30 | Jitsubo株式会社 | 肽合成方法 |
| US12024537B2 (en) | 2018-05-31 | 2024-07-02 | Sederma | Compositions and methods for chemical synthesis |
| FR3090636B1 (fr) * | 2018-12-24 | 2021-01-01 | Strainchem | Procédé de synthèse de peptides |
| EP3917937A4 (en) | 2019-02-01 | 2022-11-23 | Sederma | SYNTHETIC STRATEGY FOR A SPLIT PROTECTION GROUP |
| US12466850B2 (en) * | 2019-08-30 | 2025-11-11 | Nissan Chemical Corporation | Method for producing peptide compound |
| US20230056969A1 (en) | 2019-12-27 | 2023-02-23 | Chugai Seiyaku Kabushiki Kaisha | Method for synthesizing peptide compound |
| JP7659541B2 (ja) * | 2020-03-27 | 2025-04-09 | 株式会社カネカ | アミド結合含有化合物の製造方法 |
| JP7063408B1 (ja) | 2021-07-02 | 2022-05-09 | ペプチスター株式会社 | 液相ペプチド製造方法 |
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| US1991A (en) * | 1841-02-23 | Manner of fastening bedsteads | ||
| US5221754A (en) * | 1989-06-09 | 1993-06-22 | Research Corporation Technologies, Inc. | Reagents for rapid peptide synthesis |
| US5101059A (en) * | 1989-12-05 | 1992-03-31 | Research Corporation Technologies, Inc. | Amino acid protecting groups |
| US5877278A (en) | 1992-09-24 | 1999-03-02 | Chiron Corporation | Synthesis of N-substituted oligomers |
| US5516892A (en) | 1992-12-28 | 1996-05-14 | Indiana University Foundation | Polymer-bound mixed carboxylic anhdrides as a stable form of activated carboxylic acids |
| US6310180B1 (en) * | 1993-06-21 | 2001-10-30 | Vanderbilt University | Method for synthesis of proteins |
| US5516639A (en) * | 1993-07-22 | 1996-05-14 | Mayo Foundation For Medical Education And Research | Antibodies specific for human prostate glandular kallkrein |
| US6001966A (en) * | 1995-10-19 | 1999-12-14 | Proligo Llc | Method for solution phase synthesis of oligonucleotides and peptides |
| US5698676A (en) * | 1995-11-30 | 1997-12-16 | Abbott Laboratories | Use of propylene oxide as an acid scavenger in peptide synthesis |
| US5849954A (en) * | 1996-01-18 | 1998-12-15 | Research Corporation Technologies, Inc. | Method of peptide synthesis |
| EP0896590A1 (en) | 1996-05-03 | 1999-02-17 | Warner-Lambert Company | Rapid purification by polymer supported quench |
| US6121488A (en) * | 1997-09-24 | 2000-09-19 | Warner-Lambert Company | Quenching reagents for solution phase synthesis |
| JPH11217397A (ja) * | 1997-11-27 | 1999-08-10 | Saburo Aimoto | ペプチドチオールエステルの製造方法 |
| FR2780061B1 (fr) | 1998-06-22 | 2001-09-07 | Rhone Poulenc Rorer Sa | Nouveau procede de preparation de derives de cyclosporine |
| JP2003500415A (ja) * | 1999-05-26 | 2003-01-07 | アボット・ラボラトリーズ | イオン交換樹脂をスカベンジャーとして使用して単離処理を最も少なくしたペプチド合成方法 |
| US20020127219A1 (en) | 1999-12-30 | 2002-09-12 | Okkels Jens Sigurd | Lysosomal enzymes and lysosomal enzyme activators |
| CA2410898A1 (en) | 2000-07-19 | 2002-01-24 | Pharmacia & Upjohn Company | Substrates and assays for .beta.-secretase activity |
| IL150600A (en) * | 2001-07-19 | 2005-09-25 | Akzo Nobel Nv | Process for the preparation of compounds containing one or more amide bonds using an excess of an activated carboxylic component and scavenging the residual activated carboxylic component |
| IL150601A (en) * | 2001-07-19 | 2010-06-30 | Organon Nv | Process for rapid synthesis of peptides within a solution using the back of an activated carboxyl component and destruction of the residual activated carboxyl component |
| US20060286327A1 (en) * | 2005-06-17 | 2006-12-21 | Crawford Emmett D | Retort containers comprising polyester compositions formed from 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol |
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