JP4886702B2 - ペプチド中間体断片を使用するペプチドｔ−２０の合成 - Google Patents
ペプチド中間体断片を使用するペプチドｔ−２０の合成 Download PDFInfo
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- JP4886702B2 JP4886702B2 JP2007548732A JP2007548732A JP4886702B2 JP 4886702 B2 JP4886702 B2 JP 4886702B2 JP 2007548732 A JP2007548732 A JP 2007548732A JP 2007548732 A JP2007548732 A JP 2007548732A JP 4886702 B2 JP4886702 B2 JP 4886702B2
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- 239000012634 fragment Substances 0.000 title claims description 87
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- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005897 peptide coupling reaction Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 229940043131 pyroglutamate Drugs 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 230000005061 slumber Effects 0.000 description 1
- 229940126586 small molecule drug Drugs 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- ZFEAMMNVDPDEGE-LGRGJMMZSA-N tifuvirtide Chemical compound C([C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(C)=O)[C@@H](C)CC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)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](CCC(O)=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)C1=CC=C(O)C=C1 ZFEAMMNVDPDEGE-LGRGJMMZSA-N 0.000 description 1
- PPPHYGCRGMTZNA-UHFFFAOYSA-M trifluoromethyl sulfate Chemical compound [O-]S(=O)(=O)OC(F)(F)F PPPHYGCRGMTZNA-UHFFFAOYSA-M 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003809 water extraction Methods 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
- 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
- C07K14/08—RNA viruses
- C07K14/15—Retroviridae, e.g. bovine leukaemia virus, feline leukaemia virus human T-cell leukaemia-lymphoma virus
- C07K14/155—Lentiviridae, e.g. human immunodeficiency virus [HIV], visna-maedi virus or equine infectious anaemia virus
- C07K14/16—HIV-1 ; HIV-2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Virology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- AIDS & HIV (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64091104P | 2004-12-30 | 2004-12-30 | |
| US60/640,911 | 2004-12-30 | ||
| PCT/EP2005/013853 WO2006069728A1 (en) | 2004-12-30 | 2005-12-22 | Synthesis of peptide t-20 using peptide intermediate fragments |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008526698A JP2008526698A (ja) | 2008-07-24 |
| JP2008526698A5 JP2008526698A5 (enExample) | 2009-02-12 |
| JP4886702B2 true JP4886702B2 (ja) | 2012-02-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548732A Expired - Fee Related JP4886702B2 (ja) | 2004-12-30 | 2005-12-22 | ペプチド中間体断片を使用するペプチドｔ−２０の合成 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20060276624A1 (enExample) |
| EP (1) | EP1833843B1 (enExample) |
| JP (1) | JP4886702B2 (enExample) |
| KR (1) | KR101243013B1 (enExample) |
| CN (1) | CN101133077B (enExample) |
| AT (1) | ATE445636T1 (enExample) |
| CA (1) | CA2592438C (enExample) |
| DE (1) | DE602005017188D1 (enExample) |
| ES (1) | ES2332418T3 (enExample) |
| IL (1) | IL184080A (enExample) |
| MX (1) | MX2007007917A (enExample) |
| WO (1) | WO2006069728A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050261475A1 (en) * | 2004-02-13 | 2005-11-24 | Harvard Medical School | Solid-phase capture-release-tag methods for phosphoproteomic analyses |
| CA2593866C (en) * | 2004-12-30 | 2013-08-06 | F. Hoffmann-La Roche Ag | Synthesis of peptide t-1249 using peptide intermediate fragments |
| 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 |
| CN110372781B (zh) * | 2019-07-29 | 2021-11-16 | 深圳佳肽生物科技有限公司 | 恩夫韦肽的制备方法和应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6015881A (en) * | 1998-03-23 | 2000-01-18 | Trimeris, Inc. | Methods and compositions for peptide synthesis |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994002505A1 (en) * | 1992-07-20 | 1994-02-03 | Duke University | Compounds which inhibit hiv replication |
| US6281335B1 (en) * | 1993-10-08 | 2001-08-28 | Coulter Corporation | Hybridoma and anti-KC-4 humanized monoclonal antibody |
| US6479055B1 (en) * | 1993-06-07 | 2002-11-12 | Trimeris, Inc. | Methods for inhibition of membrane fusion-associated events, including respiratory syncytial virus transmission |
| US5464933A (en) * | 1993-06-07 | 1995-11-07 | Duke University | Synthetic peptide inhibitors of HIV transmission |
| US5817758A (en) * | 1995-06-07 | 1998-10-06 | Terrapin Technologies, Inc. | P-nitrobenzyl side-chain protection for solid-phase synthesis |
| DE69926061T2 (de) * | 1998-03-23 | 2006-06-01 | Trimeris Inc. | Verfahren und zusammensetzungen zur peptidsynthese (t-20) |
| US6469136B1 (en) * | 1999-07-07 | 2002-10-22 | Trimeris, Inc. | Methods and composition for peptide synthesis |
| US20040209999A1 (en) * | 2002-08-16 | 2004-10-21 | Bohling James Charles | Method of manufacturing polypeptides, including T-20 and T-1249, at commercial scale, and polypeptide compositions related thereto |
| AU2004200485A1 (en) * | 2003-02-25 | 2004-09-09 | Rohm And Haas Company | Method of manufacturing T-20 and T-1249 peptides at commercial scale, and T-20 and T-1249 compositions related thereto |
| CA2593866C (en) * | 2004-12-30 | 2013-08-06 | F. Hoffmann-La Roche Ag | Synthesis of peptide t-1249 using peptide intermediate fragments |
-
2005
- 2005-12-22 CA CA2592438A patent/CA2592438C/en not_active Expired - Fee Related
- 2005-12-22 DE DE602005017188T patent/DE602005017188D1/de not_active Expired - Lifetime
- 2005-12-22 AT AT05824259T patent/ATE445636T1/de active
- 2005-12-22 JP JP2007548732A patent/JP4886702B2/ja not_active Expired - Fee Related
- 2005-12-22 KR KR1020077017404A patent/KR101243013B1/ko not_active Expired - Fee Related
- 2005-12-22 EP EP05824259A patent/EP1833843B1/en not_active Expired - Lifetime
- 2005-12-22 ES ES05824259T patent/ES2332418T3/es not_active Expired - Lifetime
- 2005-12-22 MX MX2007007917A patent/MX2007007917A/es not_active Application Discontinuation
- 2005-12-22 WO PCT/EP2005/013853 patent/WO2006069728A1/en not_active Ceased
- 2005-12-22 CN CN2005800488423A patent/CN101133077B/zh not_active Expired - Fee Related
- 2005-12-30 US US11/322,323 patent/US20060276624A1/en not_active Abandoned
-
2007
- 2007-06-20 IL IL184080A patent/IL184080A/en not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6015881A (en) * | 1998-03-23 | 2000-01-18 | Trimeris, Inc. | Methods and compositions for peptide synthesis |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008526698A (ja) | 2008-07-24 |
| EP1833843A1 (en) | 2007-09-19 |
| CA2592438A1 (en) | 2006-07-06 |
| IL184080A (en) | 2010-12-30 |
| CA2592438C (en) | 2013-09-03 |
| ES2332418T3 (es) | 2010-02-04 |
| EP1833843B1 (en) | 2009-10-14 |
| CN101133077A (zh) | 2008-02-27 |
| ATE445636T1 (de) | 2009-10-15 |
| KR101243013B1 (ko) | 2013-03-14 |
| WO2006069728A1 (en) | 2006-07-06 |
| CN101133077B (zh) | 2012-09-05 |
| KR20070103400A (ko) | 2007-10-23 |
| US20060276624A1 (en) | 2006-12-07 |
| IL184080A0 (en) | 2007-10-31 |
| MX2007007917A (es) | 2007-08-14 |
| DE602005017188D1 (de) | 2009-11-26 |
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