KR900000382A - 시알산 결합 옥타펩티드 및 그의 제조방법 - Google Patents
시알산 결합 옥타펩티드 및 그의 제조방법 Download PDFInfo
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- KR900000382A KR900000382A KR1019890008805A KR890008805A KR900000382A KR 900000382 A KR900000382 A KR 900000382A KR 1019890008805 A KR1019890008805 A KR 1019890008805A KR 890008805 A KR890008805 A KR 890008805A KR 900000382 A KR900000382 A KR 900000382A
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- South Korea
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- hydrogen atom
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- formula
- sialic acid
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- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 title claims 7
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 title claims 4
- 238000002360 preparation method Methods 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- 238000000034 method Methods 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 125000006239 protecting group Chemical group 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 3
- 150000001340 alkali metals Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- -1 p-chlorobenzyloxy-carbonyl group Chemical group 0.000 claims 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- RVLOMLVNNBWRSR-KNIFDHDWSA-N (2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O RVLOMLVNNBWRSR-KNIFDHDWSA-N 0.000 claims 1
- QKZLCNQUIQIPOW-QQCJEOGWSA-N (2s)-4-amino-2-[[(2s)-2-[[2-[[2-[[(2s)-5-amino-2-[[(2s)-2-[[(2s)-6-amino-2-[[(2s)-2-aminopropanoyl]amino]hexanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]acetyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-oxobutanoic acid Chemical compound NCCCC[C@H](NC(=O)[C@@H](N)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(O)=O QKZLCNQUIQIPOW-QQCJEOGWSA-N 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 238000001354 calcination Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical compound [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000004436 sodium atom Chemical group 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/005—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Immunology (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (17)
- 다음 일반식(Ⅰ)으로 표시되는 시알산 결합 옥타펩티드 ;상시식에서 R은 수소원자 또는 아세틸기를 표시하고 R1는 저급알킬기, 아르알킬기, 수소원자 또는 알칼리 금속원자를 표시한다.
- 제1항에 있어서, 기 R'가 탄소원자수 1 내지 4의 저급알킬기, 벤질기, 펜에틸기 또는 알칼리 금속원자인 시알산 결합 옥타펩티드.
- 제2항에 있어서, 기 R'가 수소원자, 메틸기, 벤질기 및 나트륨원자로된 군에서 선택되는 시알산 옥타펩티드.
- 제1항에 있어서, 시알산 결합 옥타펩티드가 [에틸5-아세트아미드도-4,7,8,9-테트라-0-아세틸-3,5-디데옥시-α-D-글리세로-D-갈락토-2-노놀로피라노실로나토)옥시아세틸]Ala-Lys-Ser-Gln-Gly-Ser-Asn, [(메틸5-아세트아미도-3,5-디데옥시-α-D-글리세로-D-갈락토-2-노눌로피라노실로나토)옥시아세틸]Ala-Lys-Ser-Gln-Gly-Gly-Ser-Asn, 및 [(나트륨5-아세트아미도-3,5-디데옥시-α-D-글리세로-D-갈락토-2-노눌로피라노실로나토)옥시아세틸]Ala-Lys-Ser-Gln-Gly-Ser-Asn으로 구성된 군에서 서택된 일원인 시알산 결합 옥타펩티드.
- 탈소 축합체의 존재하에 다음 일반식(Ⅱ)으로 표시되는 화합물을 다음 일반식(Ⅳ)으로 표시되는 화합물과 반응시켜 일반식(Ⅲ)으로 표시되는 화합물을 형성하고, 그런뒤 팔라듐 혹의 존재하에 일반식(Ⅲ)의 화합물을 가수소분해시키는 것을 특징으로 하는 다음 일반식(Ia)으로 표시되는 시알산 결합 옥타펩티드의 제조방법.상기(Ia)식에서, R은 수소원자 또는 아세틸기를 표시하고 R'은 저급알킬기, 아르알킬기 또는 수소원자를 표시하며, 상기(Ⅱ)식에서 R은 수소원자 또는 아세틸기를 표시하고 R'는 저급알킬기, 아르알킬기 또는 수소원자를 표시하며, 상기(Ⅳ)식에서 Z1, Z2및 Z3는 각각 보호기를 표시하며, 상기(Ⅲ)식에서 R은 수소원자 또는 아세틸기를 표시하고 R'는 저급알킬기, 아르알킬기 또는 수소원자를 표시하며, Z1, Z2및 Z3는 각각 보호기를 표시한다.
- 제5항에 있어서, 기 R'가 탄소원자수 1 내지 4의 저급 알킬기, 벤질기 또는 펜에틸기인 방법,
- 제6항에 있어서, 기 R'가 수소원자, 메틸기 또는 벤질기로 구성된 군에서 선택된 일원인 방법.
- 제5항에 있어서, 보호기 Z1은 p-클로로벤질옥시-카르보닐기, t-부톡시-카르보닐기 및 벤질옥시카르보닐기로 구성된 군에서 선택된 일원이고, Z2는 벤질기 또는 t-부틸기이고, Z3은 p-니트로벨질 에스테르기 또는 t-부틸기인 방법.
- 제5항에 있어서, 탈수축합제가 1-에틸-3-(3-디메틸아미노프로필)-카르보디이미드 및 / 또는 디시클로헥실 카르보디이미드로 구성된 군에서 선택된 일원인 방법.
- 제5항에 있어서, 화합물(Ⅱ)와 (Ⅳ)간의 탈수 축합반응이 용제의 존재하에 행해지는 것을 특징으로 하는 방법.
- 제10항에 있어서, 반응이 사용되는 용제가 테트로히드로푸란, 무수 디메틸포름아미드, 무수아세톤니트릴과 무수 디메틸포름아미드의 혼합액 또는 무수 염화메틸렌과 무수 디메틸포름아미드의 혼합액으로 구성된 군에서 선택된 일원인 방법.
- 제11항에 있어서, 용제가 무수 디메틸포름아미드인 방법.
- 제5항에 있어서, 화합물(Ⅲ)의 가수소분해가 물, 아세트산 또는 그의 혼합물중에서 선택된 용제중에서 행해지는 방법.
- 제5항에 있어서, 일반식 : Ala-Lys(Z1)-Ser(Z2)-Gln(Z4)-Gly-Gly-Ser(Z2)-Asn-Z3(여기에 있어 Z1, Z2및 Z3는 상기 정의와 같고 Z4는 보호기임)으로 표시되는 화합물이 식(Ⅳ)으로 표시되는 화합물 대신 사용되는 것을 특징으로 하는 방법.
- 제14항에 있어서, 보호기 Z1이 4,4'-디메톡시벤즈히드릴기인 방법.
- 제5항에 있어서, 정의된 식(Ia)으로 표시되는 화합물을 알칼리로 처리하는 것을 특징으로 하는 다음 일반식(Ib)으로 표시되는 시알산 결합 옥타팹티드의 제조방법.상기식에서 R은 수소원자 또는 아세틸기를 표시하고 R'는 알칼리금속을 표시한다.
- 제16항에 있어서, 반응에 사용할 수 있는 알칼리는 수산화나트륨, 수산화칼륨, 탄산나트륨 및 중탄산나트륨으로 구성된 군으로부터 선택되는 것을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63159947A JPH029898A (ja) | 1988-06-28 | 1988-06-28 | シアル酸結合オクタペプチドおよびその製造方法 |
| JP88-159947 | 1988-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR900000382A true KR900000382A (ko) | 1990-01-30 |
Family
ID=15704633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890008805A KR900000382A (ko) | 1988-06-28 | 1989-06-28 | 시알산 결합 옥타펩티드 및 그의 제조방법 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4963653A (ko) |
| EP (1) | EP0348892A3 (ko) |
| JP (1) | JPH029898A (ko) |
| KR (1) | KR900000382A (ko) |
| AU (1) | AU617487B2 (ko) |
| DK (1) | DK321189A (ko) |
| FI (1) | FI893131A (ko) |
| HU (1) | HU202557B (ko) |
| IL (1) | IL90772A0 (ko) |
| NO (1) | NO892676L (ko) |
| NZ (1) | NZ229732A (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02145596A (ja) * | 1988-11-29 | 1990-06-05 | Mect Corp | 活性エステル基を持つシタル酸誘導体 |
| US5212075A (en) * | 1991-04-15 | 1993-05-18 | The Regents Of The University Of California | Compositions and methods for introducing effectors to pathogens and cells |
| FR2695391B1 (fr) * | 1992-09-04 | 1994-10-14 | Centre Nat Rech Scient | Glycopeptides, leur procédé d'obtention, et leurs applications biologiques. |
| DE102022111433A1 (de) | 2022-05-09 | 2023-11-09 | Müller Martini Holding AG | Verfahren und Anlage zur Herstellung differenter Buchblocks in einer Druckweiterverarbeitungsanlage |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5711950A (en) * | 1980-06-25 | 1982-01-21 | Kureha Chem Ind Co Ltd | Peptide and its synthesis |
| JPS59164798A (ja) * | 1983-03-09 | 1984-09-17 | Rikagaku Kenkyusho | シアル酸含有糖脂質誘導体 |
| JPS6344590A (ja) * | 1986-08-12 | 1988-02-25 | Mect Corp | シアル酸誘導体の製造方法 |
-
1988
- 1988-06-28 JP JP63159947A patent/JPH029898A/ja active Pending
-
1989
- 1989-06-27 EP EP19890111675 patent/EP0348892A3/en not_active Withdrawn
- 1989-06-27 AU AU37056/89A patent/AU617487B2/en not_active Ceased
- 1989-06-27 NO NO89892676A patent/NO892676L/no unknown
- 1989-06-27 HU HU893238A patent/HU202557B/hu not_active IP Right Cessation
- 1989-06-27 NZ NZ229732A patent/NZ229732A/en unknown
- 1989-06-27 FI FI893131A patent/FI893131A/fi not_active IP Right Cessation
- 1989-06-28 IL IL90772A patent/IL90772A0/xx unknown
- 1989-06-28 DK DK321189A patent/DK321189A/da not_active Application Discontinuation
- 1989-06-28 KR KR1019890008805A patent/KR900000382A/ko not_active Application Discontinuation
- 1989-06-28 US US07/372,708 patent/US4963653A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0348892A3 (en) | 1991-08-07 |
| IL90772A0 (en) | 1990-01-18 |
| HUT50355A (en) | 1990-01-29 |
| DK321189A (da) | 1989-12-29 |
| JPH029898A (ja) | 1990-01-12 |
| EP0348892A2 (en) | 1990-01-03 |
| NO892676D0 (no) | 1989-06-27 |
| FI893131A (fi) | 1989-12-29 |
| FI893131A0 (fi) | 1989-06-27 |
| HU202557B (en) | 1991-03-28 |
| US4963653A (en) | 1990-10-16 |
| DK321189D0 (da) | 1989-06-28 |
| NZ229732A (en) | 1991-06-25 |
| NO892676L (no) | 1989-12-29 |
| AU617487B2 (en) | 1991-11-28 |
| AU3705689A (en) | 1990-01-04 |
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