SE503255C2 - Förfarande för reduktion av metioninsulfoxidrester - Google Patents
Förfarande för reduktion av metioninsulfoxidresterInfo
- Publication number
- SE503255C2 SE503255C2 SE8802941A SE8802941A SE503255C2 SE 503255 C2 SE503255 C2 SE 503255C2 SE 8802941 A SE8802941 A SE 8802941A SE 8802941 A SE8802941 A SE 8802941A SE 503255 C2 SE503255 C2 SE 503255C2
- Authority
- SE
- Sweden
- Prior art keywords
- acid
- peptide
- residues
- concentration
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title claims abstract description 22
- QEFRNWWLZKMPFJ-YGVKFDHGSA-N L-methionine (R)-S-oxide group Chemical group N[C@@H](CCS(=O)C)C(=O)O QEFRNWWLZKMPFJ-YGVKFDHGSA-N 0.000 title claims abstract description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 64
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 60
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 29
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 19
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 19
- 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims abstract description 18
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229940071870 hydroiodic acid Drugs 0.000 claims abstract description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical group CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 62
- 239000002253 acid Substances 0.000 claims description 18
- 125000001475 halogen functional group Chemical group 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000012429 reaction media Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 21
- 230000009467 reduction Effects 0.000 description 16
- 235000018102 proteins Nutrition 0.000 description 13
- 108060003199 Glucagon Proteins 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 102000051325 Glucagon Human genes 0.000 description 8
- 229960004666 glucagon Drugs 0.000 description 8
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 7
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 6
- 102000004218 Insulin-Like Growth Factor I Human genes 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000007385 chemical modification Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QEFRNWWLZKMPFJ-ZXPFJRLXSA-N L-methionine (R)-S-oxide Chemical compound C[S@@](=O)CC[C@H]([NH3+])C([O-])=O QEFRNWWLZKMPFJ-ZXPFJRLXSA-N 0.000 description 3
- QEFRNWWLZKMPFJ-UHFFFAOYSA-N L-methionine sulphoxide Natural products CS(=O)CCC(N)C(O)=O QEFRNWWLZKMPFJ-UHFFFAOYSA-N 0.000 description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000004254 Ammonium phosphate Substances 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 2
- 235000019289 ammonium phosphates Nutrition 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- ZKLRYZNOOWOOMP-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;trifluoromethanesulfonic acid Chemical compound OC(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F ZKLRYZNOOWOOMP-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- NOKPBJYHPHHWAN-REOHCLBHSA-N S-sulfo-L-cysteine Chemical compound OC(=O)[C@@H](N)CSS(O)(=O)=O NOKPBJYHPHHWAN-REOHCLBHSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 235000010335 lysozyme Nutrition 0.000 description 1
- 229960000274 lysozyme Drugs 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
- IOPLHGOSNCJOOO-UHFFFAOYSA-N methyl 3,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C(N)=C1 IOPLHGOSNCJOOO-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- ZERULLAPCVRMCO-UHFFFAOYSA-N sulfure de di n-propyle Natural products CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 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
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/067—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for sulfur-containing functions
-
- 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
- C07K1/122—Hydrolysis with acids different from HF
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)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/088,739 US4835254A (en) | 1987-08-24 | 1987-08-24 | Process for reducing methionine sulfoxide residues in peptides or proteins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8802941D0 SE8802941D0 (sv) | 1988-08-19 |
| SE8802941L SE8802941L (sv) | 1989-02-25 |
| SE503255C2 true SE503255C2 (sv) | 1996-04-29 |
Family
ID=22213162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8802941A SE503255C2 (sv) | 1987-08-24 | 1988-08-19 | Förfarande för reduktion av metioninsulfoxidrester |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4835254A (ref) |
| JP (1) | JPH02262590A (ref) |
| KR (1) | KR890003798A (ref) |
| CN (1) | CN1029976C (ref) |
| BE (1) | BE1004198A3 (ref) |
| CA (1) | CA1315482C (ref) |
| CH (1) | CH675879A5 (ref) |
| DE (1) | DE3828287A1 (ref) |
| DK (1) | DK465588A (ref) |
| FR (1) | FR2619820B1 (ref) |
| GB (1) | GB2209033B (ref) |
| HU (1) | HU200438B (ref) |
| IL (1) | IL87479A (ref) |
| IT (1) | IT1226864B (ref) |
| NL (1) | NL8802041A (ref) |
| SE (1) | SE503255C2 (ref) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2682061B2 (ja) * | 1988-10-07 | 1997-11-26 | 藤沢薬品工業株式会社 | ペプチドの分子内ジスルフィド結合の形成法 |
| US5272135A (en) * | 1991-03-01 | 1993-12-21 | Chiron Ophthalmics, Inc. | Method for the stabilization of methionine-containing polypeptides |
| GB2451441B (en) | 2007-07-30 | 2012-07-11 | Lein Applied Diagnostics Ltd | Optical alignment apparatus and method thereof |
| KR102650195B1 (ko) | 2020-11-11 | 2024-04-09 | 주식회사 제론메드 | 유리 메티오닌ｒ설폭사이드를 정량적으로 측정할 수 있는 형광단백질 센서 및 이의 용도 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4745178A (en) * | 1987-04-22 | 1988-05-17 | Eli Lilly And Company | Process for selective peptide bond cleavage using sulfoxides and CF3 CO |
-
1987
- 1987-08-24 US US07/088,739 patent/US4835254A/en not_active Expired - Lifetime
-
1988
- 1988-08-12 CH CH3045/88A patent/CH675879A5/de not_active IP Right Cessation
- 1988-08-16 CA CA000574821A patent/CA1315482C/en not_active Expired - Fee Related
- 1988-08-17 NL NL8802041A patent/NL8802041A/nl not_active Application Discontinuation
- 1988-08-17 IL IL87479A patent/IL87479A/xx not_active IP Right Cessation
- 1988-08-18 IT IT8821716A patent/IT1226864B/it active
- 1988-08-19 KR KR1019880010521A patent/KR890003798A/ko not_active Ceased
- 1988-08-19 DE DE3828287A patent/DE3828287A1/de not_active Withdrawn
- 1988-08-19 SE SE8802941A patent/SE503255C2/sv not_active IP Right Cessation
- 1988-08-19 DK DK465588A patent/DK465588A/da unknown
- 1988-08-22 BE BE8800956A patent/BE1004198A3/fr not_active IP Right Cessation
- 1988-08-22 FR FR8811081A patent/FR2619820B1/fr not_active Expired - Lifetime
- 1988-08-22 GB GB8819861A patent/GB2209033B/en not_active Expired - Lifetime
- 1988-08-22 CN CN88106236A patent/CN1029976C/zh not_active Expired - Fee Related
- 1988-08-23 JP JP63209319A patent/JPH02262590A/ja active Pending
- 1988-08-23 HU HU884435A patent/HU200438B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL87479A0 (en) | 1989-01-31 |
| DK465588A (da) | 1989-03-17 |
| IT8821716A0 (it) | 1988-08-18 |
| GB2209033B (en) | 1991-01-02 |
| US4835254A (en) | 1989-05-30 |
| JPH02262590A (ja) | 1990-10-25 |
| NL8802041A (nl) | 1989-03-16 |
| GB2209033A (en) | 1989-04-26 |
| KR890003798A (ko) | 1989-04-18 |
| CN1031538A (zh) | 1989-03-08 |
| DE3828287A1 (de) | 1989-03-09 |
| DK465588D0 (da) | 1988-08-19 |
| IT1226864B (it) | 1991-02-20 |
| BE1004198A3 (fr) | 1992-10-13 |
| FR2619820B1 (fr) | 1992-11-13 |
| FR2619820A1 (fr) | 1989-03-03 |
| CA1315482C (en) | 1993-03-30 |
| CH675879A5 (ref) | 1990-11-15 |
| HU200438B (en) | 1990-06-28 |
| CN1029976C (zh) | 1995-10-11 |
| GB8819861D0 (en) | 1988-09-21 |
| SE8802941L (sv) | 1989-02-25 |
| HUT48560A (en) | 1989-06-28 |
| SE8802941D0 (sv) | 1988-08-19 |
| IL87479A (en) | 1993-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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