TWI233931B - Methods and compositions for peptide synthesis - Google Patents
Methods and compositions for peptide synthesis Download PDFInfo
- Publication number
- TWI233931B TWI233931B TW088104562A TW88104562A TWI233931B TW I233931 B TWI233931 B TW I233931B TW 088104562 A TW088104562 A TW 088104562A TW 88104562 A TW88104562 A TW 88104562A TW I233931 B TWI233931 B TW I233931B
- Authority
- TW
- Taiwan
- Prior art keywords
- peptide
- fmoc
- side chain
- minutes
- tbu
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 107
- 238000010647 peptide synthesis reaction Methods 0.000 title description 8
- 239000000203 mixture Substances 0.000 title description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 173
- PEASPLKKXBYDKL-FXEVSJAOSA-N enfuvirtide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(C)=O)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 PEASPLKKXBYDKL-FXEVSJAOSA-N 0.000 claims abstract description 84
- 108010033276 Peptide Fragments Proteins 0.000 claims abstract description 44
- 102000007079 Peptide Fragments Human genes 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
- 150000001412 amines Chemical class 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 14
- 230000002194 synthesizing effect Effects 0.000 claims description 8
- 230000004048 modification Effects 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 5
- FAOSXBASBLDSBE-LZGXBFJGSA-N (4S)-5-[[(2S)-6-amino-1-[[(2S)-4-amino-1-[[(2S)-1-[[(2S)-5-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-6-amino-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-4-amino-1-[[(2S)-1-[[(1S)-1-carboxy-2-phenylethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxohexan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-carboxy-1-oxobutan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-4-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoic acid Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)[C@@H](C)O)[C@@H](C)CC)C1=CN=CN1 FAOSXBASBLDSBE-LZGXBFJGSA-N 0.000 claims 1
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- 125000003275 alpha amino acid group Chemical group 0.000 description 14
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- FPIRBHDGWMWJEP-UHFFFAOYSA-N 1-hydroxy-7-azabenzotriazole Chemical compound C1=CN=C2N(O)N=NC2=C1 FPIRBHDGWMWJEP-UHFFFAOYSA-N 0.000 description 11
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- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
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- 238000002953 preparative HPLC Methods 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- 239000006104 solid solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ADOHASQZJSJZBT-SANMLTNESA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]propanoic acid Chemical compound C12=CC=CC=C2N(C(=O)OC(C)(C)C)C=C1C[C@@H](C(O)=O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 ADOHASQZJSJZBT-SANMLTNESA-N 0.000 description 1
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- KSDTXRUIZMTBNV-INIZCTEOSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)butanedioic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CC(=O)O)C(O)=O)C3=CC=CC=C3C2=C1 KSDTXRUIZMTBNV-INIZCTEOSA-N 0.000 description 1
- VVQIIIAZJXTLRE-QMMMGPOBSA-N (2s)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound CC(C)(C)OC(=O)NCCCC[C@H](N)C(O)=O VVQIIIAZJXTLRE-QMMMGPOBSA-N 0.000 description 1
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- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
- IACWJZMJRQJJSI-UHFFFAOYSA-N 1-hydroxybenzotriazole;trihydrate Chemical compound O.O.O.C1=CC=C2N(O)N=NC2=C1 IACWJZMJRQJJSI-UHFFFAOYSA-N 0.000 description 1
- MJZMSEWWBGCBFM-UHFFFAOYSA-N 2-(2-acetamidopropanoylamino)propanoic acid Chemical compound OC(=O)C(C)NC(=O)C(C)NC(C)=O MJZMSEWWBGCBFM-UHFFFAOYSA-N 0.000 description 1
- CSZKOERVDCFYBX-UHFFFAOYSA-N 2-methoxy-2-phenoxybutanoic acid Chemical compound CCC(OC)(C(O)=O)OC1=CC=CC=C1 CSZKOERVDCFYBX-UHFFFAOYSA-N 0.000 description 1
- DWPYQDGDWBKJQL-UHFFFAOYSA-N 2-pyridin-4-ylethanol Chemical compound OCCC1=CC=NC=C1 DWPYQDGDWBKJQL-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- NBVILZRLOFYXMF-UHFFFAOYSA-N 9h-fluorene;piperidine Chemical compound C1CCNCC1.C1=CC=C2CC3=CC=CC=C3C2=C1 NBVILZRLOFYXMF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IPWKGIFRRBGCJO-IMJSIDKUSA-N Ala-Ser Chemical compound C[C@H]([NH3+])C(=O)N[C@@H](CO)C([O-])=O IPWKGIFRRBGCJO-IMJSIDKUSA-N 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- QNBVTHNJGCOVFA-AVGNSLFASA-N Leu-Leu-Glu Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CCC(O)=O QNBVTHNJGCOVFA-AVGNSLFASA-N 0.000 description 1
- 229910014288 N-N Inorganic materials 0.000 description 1
- HDAXUHAUNCRXAE-UHFFFAOYSA-N N1CCCCC1.C(C1=CC=CC=C1)C1=CC=CC1=C Chemical compound N1CCCCC1.C(C1=CC=CC=C1)C1=CC=CC1=C HDAXUHAUNCRXAE-UHFFFAOYSA-N 0.000 description 1
- 229910014320 N—N Inorganic materials 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 240000007313 Tilia cordata Species 0.000 description 1
- 101800001690 Transmembrane protein gp41 Proteins 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- UESYMIFUVPHBHL-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O.CC(O)=O.CC(O)=O UESYMIFUVPHBHL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 125000000613 asparagine group Chemical group N[C@@H](CC(N)=O)C(=O)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 210000004899 c-terminal region Anatomy 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012468 concentrated sample Substances 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- LBGWCDQCRMORLC-UHFFFAOYSA-N ethanol methane Chemical compound C[H].[H]C([H])[H].[H]CC([H])O LBGWCDQCRMORLC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000803 paradoxical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 229910021332 silicide Inorganic materials 0.000 description 1
- FVBUAEGBCNSCDD-UHFFFAOYSA-N silicide(4-) Chemical compound [Si-4] FVBUAEGBCNSCDD-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000012085 test solution Substances 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
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/005—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from viruses
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N2740/00—Reverse transcribing RNA viruses
- C12N2740/00011—Details
- C12N2740/10011—Retroviridae
- C12N2740/16011—Human Immunodeficiency Virus, HIV
- C12N2740/16111—Human Immunodeficiency Virus, HIV concerning HIV env
- C12N2740/16122—New viral proteins or individual genes, new structural or functional aspects of known viral proteins or genes
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/045,920 US6281331B1 (en) | 1998-03-23 | 1998-03-23 | Methods and compositions for peptide synthesis |
| US09/071,877 US6015881A (en) | 1998-03-23 | 1998-05-01 | Methods and compositions for peptide synthesis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI233931B true TWI233931B (en) | 2005-06-11 |
Family
ID=26723345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088104562A TWI233931B (en) | 1998-03-23 | 1999-03-23 | Methods and compositions for peptide synthesis |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1071442B9 (enExample) |
| JP (1) | JP4602547B2 (enExample) |
| CN (1) | CN100383158C (enExample) |
| AT (1) | ATE299029T1 (enExample) |
| AU (1) | AU751358B2 (enExample) |
| BR (1) | BR9909018A (enExample) |
| CA (1) | CA2324348C (enExample) |
| DE (1) | DE69926061T2 (enExample) |
| DK (1) | DK1071442T3 (enExample) |
| ES (1) | ES2245505T3 (enExample) |
| NZ (1) | NZ507083A (enExample) |
| TW (1) | TWI233931B (enExample) |
| WO (1) | WO1999048513A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6281331B1 (en) * | 1998-03-23 | 2001-08-28 | Trimeris, Inc. | Methods and compositions for peptide synthesis |
| US6469136B1 (en) * | 1999-07-07 | 2002-10-22 | Trimeris, Inc. | Methods and composition for peptide synthesis |
| ES2525317T3 (es) | 2001-06-15 | 2014-12-22 | F. Hoffmann-La Roche Ag | Producción recombinante de inhibidores de la fusión antivirales peptídicos |
| AU2003257467B2 (en) * | 2002-07-24 | 2008-02-28 | F. Hoffmann-La Roche Ag | Pegylated T20 polypeptide |
| DE602004017057D1 (de) | 2003-12-31 | 2008-11-20 | Hoffmann La Roche | Verfahren und systeme zur rückgewinnung von peptiden |
| EP1701976A2 (en) * | 2003-12-31 | 2006-09-20 | F.Hoffmann-La Roche Ag | Peptide synthesis and deprotection with co-solvent |
| EP1701969B1 (en) | 2003-12-31 | 2007-10-24 | F.Hoffmann-La Roche Ag | Process for peptide synthesis using a reduced amount of deprotection agent |
| CA2592438C (en) * | 2004-12-30 | 2013-09-03 | F.Hoffmann-La Roche Ag | Synthesis of peptide t-20 using peptide intermediate fragments |
| CA2651070A1 (en) | 2006-05-03 | 2007-11-15 | Mallinckrodt Inc. | Composition and method for the release of protected peptides from a resin |
| WO2009014177A1 (ja) * | 2007-07-25 | 2009-01-29 | Ajinomoto Co., Inc. | ジベンゾフルベン誘導体の淘汰方法 |
| JP5473925B2 (ja) * | 2007-10-27 | 2014-04-16 | コーデン ファーマ コロラド インコーポレイテッド | 固相および溶液相の組み合わせ技法を使用するインスリン分泌性ペプチドの合成 |
| AU2008334783A1 (en) * | 2007-12-11 | 2009-06-18 | F. Hoffmann-La Roche Ag | Insulinotropic peptide synthesis using solid and solution phase combination techniques |
| EP2322498B1 (en) * | 2008-08-06 | 2014-04-16 | Ajinomoto Co., Inc. | Processes for removing dibenzofulvene |
| US20110288235A1 (en) * | 2008-09-03 | 2011-11-24 | Scinopharm Taiwan Ltd. | Process for the Preparation of Pramlintide |
| AU2009288036A1 (en) * | 2008-09-03 | 2010-03-11 | Scinopharm Taiwan, Ltd. | Process for the preparation of pramlintide |
| WO2011095989A2 (en) * | 2010-02-04 | 2011-08-11 | Matrix Laboratories Ltd | An improved process for the preparation of enfuvirtide |
| PL219569B1 (pl) * | 2010-02-19 | 2015-05-29 | Peptaderm Spółka Z Ograniczoną Odpowiedzialnością | Cykliczne tetrapeptydy i ich zastosowanie |
| CN103374054B (zh) * | 2012-04-28 | 2014-12-24 | 上海第一生化药业有限公司 | 一步法固相合成多肽的方法 |
| GB201315335D0 (en) | 2013-08-29 | 2013-10-09 | Of Singapore | Amino diacids containing peptide modifiers |
| CA3167047A1 (en) * | 2020-02-05 | 2021-08-12 | Martin D. Johnson | Three resin reactors in series peptide synthesizer |
| CN114315957B (zh) * | 2021-12-30 | 2023-07-07 | 深圳瑞德林生物技术有限公司 | 一种多肽的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987007616A1 (en) * | 1986-06-12 | 1987-12-17 | Biogen N.V. | Peptides involved in the pathogenesis of hiv infection |
| US4787222A (en) * | 1986-11-24 | 1988-11-29 | Novatek Medical Inc. | Combination lock for blood identification system |
| US5444044A (en) * | 1992-03-26 | 1995-08-22 | New York Blood Center | Synthetic polypeptides as inhibitors of HIV-1 |
| US6479055B1 (en) * | 1993-06-07 | 2002-11-12 | Trimeris, Inc. | Methods for inhibition of membrane fusion-associated events, including respiratory syncytial virus transmission |
| EP0708659A4 (en) * | 1993-06-07 | 2000-08-23 | Genentech Inc | HIV ENVELOPE POLYPEPTIDE |
| US5464933A (en) * | 1993-06-07 | 1995-11-07 | Duke University | Synthetic peptide inhibitors of HIV transmission |
| JPH09502348A (ja) * | 1993-09-11 | 1997-03-11 | ポリムン・シエンティフィーク・イムノビオロギッシェ・フォルシュング・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 遺伝学的に分岐したｈｉｖ−１株に対する中和抗体を誘導するペプチド |
| AU722895B2 (en) * | 1996-02-09 | 2000-08-10 | F. Hoffmann-La Roche Ag | Synthesis of VIP analog |
-
1999
- 1999-03-22 DE DE69926061T patent/DE69926061T2/de not_active Expired - Lifetime
- 1999-03-22 EP EP99912802A patent/EP1071442B9/en not_active Expired - Lifetime
- 1999-03-22 NZ NZ507083A patent/NZ507083A/en not_active IP Right Cessation
- 1999-03-22 CN CNB998064319A patent/CN100383158C/zh not_active Expired - Fee Related
- 1999-03-22 AU AU31097/99A patent/AU751358B2/en not_active Expired
- 1999-03-22 CA CA002324348A patent/CA2324348C/en not_active Expired - Lifetime
- 1999-03-22 ES ES99912802T patent/ES2245505T3/es not_active Expired - Lifetime
- 1999-03-22 AT AT99912802T patent/ATE299029T1/de active
- 1999-03-22 DK DK99912802T patent/DK1071442T3/da active
- 1999-03-22 BR BR9909018-0A patent/BR9909018A/pt not_active IP Right Cessation
- 1999-03-22 WO PCT/US1999/006230 patent/WO1999048513A1/en not_active Ceased
- 1999-03-22 JP JP2000537561A patent/JP4602547B2/ja not_active Expired - Fee Related
- 1999-03-23 TW TW088104562A patent/TWI233931B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU751358B2 (en) | 2002-08-15 |
| NZ507083A (en) | 2003-10-31 |
| ES2245505T3 (es) | 2006-01-01 |
| CN100383158C (zh) | 2008-04-23 |
| AU3109799A (en) | 1999-10-18 |
| ATE299029T1 (de) | 2005-07-15 |
| WO1999048513A1 (en) | 1999-09-30 |
| JP4602547B2 (ja) | 2010-12-22 |
| JP2002507576A (ja) | 2002-03-12 |
| DK1071442T3 (da) | 2005-10-24 |
| CN1303299A (zh) | 2001-07-11 |
| EP1071442A4 (en) | 2002-06-05 |
| EP1071442B1 (en) | 2005-07-06 |
| DE69926061T2 (de) | 2006-06-01 |
| EP1071442B9 (en) | 2006-01-18 |
| CA2324348A1 (en) | 1999-09-30 |
| EP1071442A1 (en) | 2001-01-31 |
| DE69926061D1 (de) | 2005-08-11 |
| CA2324348C (en) | 2006-03-14 |
| BR9909018A (pt) | 2001-10-16 |
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