KR920014823A - β-푸코피라노실 인산염 및 순수 GDP-푸코스의 입체선택적 제조방법 - Google Patents
β-푸코피라노실 인산염 및 순수 GDP-푸코스의 입체선택적 제조방법 Download PDFInfo
- Publication number
- KR920014823A KR920014823A KR1019920001300A KR920001300A KR920014823A KR 920014823 A KR920014823 A KR 920014823A KR 1019920001300 A KR1019920001300 A KR 1019920001300A KR 920001300 A KR920001300 A KR 920001300A KR 920014823 A KR920014823 A KR 920014823A
- Authority
- KR
- South Korea
- Prior art keywords
- fucose
- fucopyranosyl
- phosphate
- process according
- acetyl
- Prior art date
Links
- PTVXQARCLQPGIR-SXUWKVJYSA-N beta-L-fucose 1-phosphate Chemical compound C[C@@H]1O[C@H](OP(O)(O)=O)[C@@H](O)[C@H](O)[C@@H]1O PTVXQARCLQPGIR-SXUWKVJYSA-N 0.000 title claims description 6
- 230000000707 stereoselective effect Effects 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title claims 2
- LQEBEXMHBLQMDB-UHFFFAOYSA-N GDP-L-fucose Natural products OC1C(O)C(O)C(C)OC1OP(O)(=O)OP(O)(=O)OCC1C(O)C(O)C(N2C3=C(C(N=C(N)N3)=O)N=C2)O1 LQEBEXMHBLQMDB-UHFFFAOYSA-N 0.000 title 1
- LQEBEXMHBLQMDB-JGQUBWHWSA-N GDP-beta-L-fucose Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@@H]1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=C(C(NC(N)=N3)=O)N=C2)O1 LQEBEXMHBLQMDB-JGQUBWHWSA-N 0.000 title 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 4
- SHZGCJCMOBCMKK-PQMKYFCFSA-N L-Fucose Natural products C[C@H]1O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]1O SHZGCJCMOBCMKK-PQMKYFCFSA-N 0.000 claims description 4
- PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 10
- LQEBEXMHBLQMDB-QIXZNPMTSA-N GDP-L-fucose Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)OC1OP(O)(=O)OP(O)(=O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=C(C(NC(N)=N3)=O)N=C2)O1 LQEBEXMHBLQMDB-QIXZNPMTSA-N 0.000 claims 3
- SHZGCJCMOBCMKK-DHVFOXMCSA-N L-fucopyranose Chemical compound C[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@@H]1O SHZGCJCMOBCMKK-DHVFOXMCSA-N 0.000 claims 3
- RQFCJASXJCIDSX-UUOKFMHZSA-N guanosine 5'-monophosphate Chemical class C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O RQFCJASXJCIDSX-UUOKFMHZSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000003480 eluent Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- -1 nosyl phosphate Chemical compound 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- YFHNDHXQDJQEEE-UHFFFAOYSA-N acetic acid;hydrazine Chemical compound NN.CC(O)=O YFHNDHXQDJQEEE-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 235000013928 guanylic acid Nutrition 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical class CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 238000002953 preparative HPLC Methods 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000008481 L-fucoses Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
- C07H19/207—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 삼치환 L-푸코스의 반응 합성도이다, 제2도는β-L-푸코피라노실 인산염의 반응 합성도이다.
Claims (10)
- 2,3 및 4위치가 보호된 L-푸코스는 상응하는 O-(α-L-푸코피라노실) 트리클로로아세트이미데이트로 전환시키고, 이 반응물은 일반식 PO(OH)(OR)2(여기에서, R은 C1-C4-알킬, 페닐 또는 벤질)의 절대적 산-유리 유기인산염과 반응시키고, 푸코피라노실 고리상의 인산염기의 라디칼 R 및 보호기를 제거하고,β-L-푸코피라노실 인산염을 염으로서 분리하는 것을 특징으로 하는β-L-푸코피라노실 인산염의 입체선택적 제조방법.
- 제1항에 있어서, 아세틸 또는 벤질을 보호기로서 사용하는 것을 특징으로 하는 제조방법.
- 제1항 또는 제2항에 있어서, 보호된 L-푸코스가 수소화나트륨과 선택적으로 반응하여 상응하는α-트리클로로아세트이미데이트를 수득하는 것을 특징으로 하는 제조방법.
- 제1항 내지 제3항중 어느 한항에 있어서, 2,3,4-트리-O-아세틸-L-푸코스가 일-단계 반응으로 테트라-아세틸화된 L-푸코스로부터 제조되는 것을 특징으로 하는 제조방법.
- 제4항에 있어서, 테트라-O-아세틸-L-푸코스의 아노머 아세틸기는 히드라진 아세테이트로 제거하는 것을 특징으로 하는 제조방법.
- β-L-푸코피라노실 인산염을 용이하게 가용성 염으로 전환시키고, 이 화합물을 활성화된 구아노신 모노포스페이트(GMP)와 반응시키고, 형성된 GDP-푸코스는 용리액으로서 휘발성 완충계를 사용하여 예비 HPLC의 방법으로 정제하는 것을 특징으로 하는 매우 순수한 구아노신 이인산염-푸코스(GDP-푸코스)의 입체선택적 제조방법.
- 제6항에 있어서,β-L-푸코피라노실 인산염을 트리-n-옥틸암모늄염으로 전환하는 것을 특징으로 하는 제조방법.
- 제6항 또는 제7항에 있어서, GMP-모르폴리데이트를 활성화된 GMP로서 사용하는 것을 특징으로 하는 제조방법.
- 제6항 내지 제8항중 어느 한항에 있어서, 트리에틸암모늄탄화수소를 예비 정제에 대한 용리액으로서 사용하는 것을 특징으로 하는 제조방법.
- 제6항 내지 제9항중 어느 한항에 있어서, 사용된β-L-푸코피라노실 인산염을 제1항 내지 제5항중 어느 한항에 의해 제조하는 것을 특징으로 하는 GDP-푸코스 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4102817.1 | 1991-01-31 | ||
| DE4102817A DE4102817A1 (de) | 1991-01-31 | 1991-01-31 | Verfahren zur stereoselektiven herstellung von (beta)-fucopyranosyl-phosphaten und sehr reiner gdp-fucose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920014823A true KR920014823A (ko) | 1992-08-25 |
Family
ID=6424052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019920001300A KR920014823A (ko) | 1991-01-31 | 1992-01-29 | β-푸코피라노실 인산염 및 순수 GDP-푸코스의 입체선택적 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5371203A (ko) |
| EP (1) | EP0502298A3 (ko) |
| JP (1) | JPH04312598A (ko) |
| KR (1) | KR920014823A (ko) |
| AU (1) | AU653383B2 (ko) |
| CA (1) | CA2060283A1 (ko) |
| CS (1) | CS27092A3 (ko) |
| DE (1) | DE4102817A1 (ko) |
| HU (1) | HUT61316A (ko) |
| IE (1) | IE920313A1 (ko) |
| MX (1) | MX9200375A (ko) |
| PT (1) | PT100073A (ko) |
| TW (1) | TW206233B (ko) |
| ZA (1) | ZA92720B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU7449700A (en) * | 1999-09-30 | 2001-04-30 | Yamasa Corporation | Highly pure guanosine 5'-diphosphate fucose and process for producing the same |
| US7038039B2 (en) | 2000-02-10 | 2006-05-02 | Mitsui Chemicals, Inc. | Process for selectively producing 1-phosphorylated sugar derivative anomer and process for producing nucleoside |
| WO2012127045A1 (en) | 2011-03-23 | 2012-09-27 | Glycode | A yeast recombinant cell capable of producing gdp-fucose |
| CN114990175B (zh) * | 2021-10-22 | 2023-03-31 | 岩唐生物科技(杭州)有限责任公司 | 一种岩藻糖衍生物的合成方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3127933A1 (de) * | 1980-07-18 | 1982-04-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (delta)- oder (beta)-o-glycosyimidaten |
| EP0146810A3 (de) * | 1983-12-05 | 1987-05-13 | Solco Basel AG | Verfahren zur Herstellung von Sphingosinderivaten |
| US4987271A (en) * | 1989-02-17 | 1991-01-22 | Asahi Glass Company, Ltd. | Method for purifying a polyoxyalkylene alcohol |
-
1991
- 1991-01-31 DE DE4102817A patent/DE4102817A1/de not_active Ceased
-
1992
- 1992-01-23 EP EP92101070A patent/EP0502298A3/de not_active Withdrawn
- 1992-01-29 MX MX9200375A patent/MX9200375A/es unknown
- 1992-01-29 KR KR1019920001300A patent/KR920014823A/ko not_active Application Discontinuation
- 1992-01-29 CA CA002060283A patent/CA2060283A1/en not_active Abandoned
- 1992-01-29 AU AU10540/92A patent/AU653383B2/en not_active Expired - Fee Related
- 1992-01-30 CS CS92270A patent/CS27092A3/cs unknown
- 1992-01-30 IE IE031392A patent/IE920313A1/en unknown
- 1992-01-30 HU HU9200280A patent/HUT61316A/hu unknown
- 1992-01-30 PT PT100073A patent/PT100073A/pt not_active Application Discontinuation
- 1992-01-31 US US07/828,617 patent/US5371203A/en not_active Expired - Fee Related
- 1992-01-31 JP JP4040712A patent/JPH04312598A/ja active Pending
- 1992-01-31 ZA ZA92720A patent/ZA92720B/xx unknown
- 1992-02-24 TW TW081101410A patent/TW206233B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| AU653383B2 (en) | 1994-09-29 |
| ZA92720B (en) | 1992-12-30 |
| EP0502298A2 (de) | 1992-09-09 |
| PT100073A (pt) | 1993-03-31 |
| EP0502298A3 (en) | 1995-01-11 |
| HU9200280D0 (en) | 1992-05-28 |
| CA2060283A1 (en) | 1992-08-01 |
| MX9200375A (es) | 1992-12-01 |
| HUT61316A (en) | 1992-12-28 |
| US5371203A (en) | 1994-12-06 |
| IE920313A1 (en) | 1992-09-09 |
| TW206233B (ko) | 1993-05-21 |
| DE4102817A1 (de) | 1992-08-06 |
| JPH04312598A (ja) | 1992-11-04 |
| CS27092A3 (en) | 1992-08-12 |
| AU1054092A (en) | 1992-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ATE38386T1 (de) | Verfahren zur herstellung von oligonucleotiden. | |
| JPS5622396A (en) | Detergent composition | |
| KR830006156A (ko) | 치환된 할로겐부위를 갖는 플루오로카본 에테르의 제조방법 | |
| IL60861A0 (en) | Compound obtained from microorganisms of the genus streptomyces, process for the preparation thereof and process for the preparation of anthelmintic and acaricidal compositions containing it | |
| YU47791B (sr) | Postupak za dobijanje dideoksihidrokar-bocikličnih nukleozida | |
| KR840004761A (ko) | N-글리코실화 카복스아미드 유도체의 제조방법 | |
| KR850007435A (ko) | 9a-아자-9a-호모에리트로마이신 유도체의 제조방법 | |
| KR860003256A (ko) | 아데노신의 n^6-치환된 데옥시리보스 유사체의 제조방법 | |
| IE821872L (en) | Amine derivatives. | |
| KR920014823A (ko) | β-푸코피라노실 인산염 및 순수 GDP-푸코스의 입체선택적 제조방법 | |
| KR870008911A (ko) | 카르보사이클릭 퓨린 누클레오시드, 그의 제조방법 및 용도 | |
| ES408274A1 (es) | Procedimiento para la preparacion de 2-(furilmetil)-6,7- benzomorfanos. | |
| KR900012961A (ko) | 유기실리콘 화합물의 제조방법 | |
| KR960010674A (ko) | 알킬 폴리글리코시드의 제조방법 | |
| DE3163814D1 (en) | Homocitric acid oligoriboside derivatives, process for their manufacture and their use as preventives of dental caries | |
| GB1240087A (en) | N(6)-alkyl-adenosine derivatives | |
| JPS57146798A (en) | Hexosyl nucleoside derivative | |
| KR840004126A (ko) | 2-β-D-리보푸라노실셀레나졸-4-카르복사미드 화합물의 제조방법 | |
| SE8004621L (sv) | Bensimidazolderivat | |
| GB2002773A (en) | Oligonucleotide inhibitors of protein synthesis | |
| KR890011883A (ko) | 5,8,13,14-테트라하이드로벤즈[5,6]이소인돌로[2,1-b]이소퀴놀린-8,13-디온 유도체의 제조방법 | |
| JPS5634698A (en) | N6-acyl-3'-o(o-nitrobenzyl)adenosine-5'-monophosphate and its preparation | |
| KR940021558A (ko) | 신규한 결정성 세팔로스포린 유도체의 제조방법 | |
| JPS5239699A (en) | Improved methods of producing adenosine derivatives | |
| JPS5427582A (en) | Preparation of dinucleoside triphosphate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |