AU712149B2 - Methods of synthesizing GM2 - Google Patents
Methods of synthesizing GM2 Download PDFInfo
- Publication number
- AU712149B2 AU712149B2 AU18586/97A AU1858697A AU712149B2 AU 712149 B2 AU712149 B2 AU 712149B2 AU 18586/97 A AU18586/97 A AU 18586/97A AU 1858697 A AU1858697 A AU 1858697A AU 712149 B2 AU712149 B2 AU 712149B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- group
- catalyst
- trifluoromethanesulfonate
- trisaccharide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 56
- 230000002194 synthesizing effect Effects 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 92
- -1 trisaccharide compound Chemical class 0.000 claims description 37
- 239000000348 glycosyl donor Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 11
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 6
- 239000000937 glycosyl acceptor Substances 0.000 claims description 6
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- RBGLVWCAGPITBS-UHFFFAOYSA-L bis(trifluoromethylsulfonyloxy)tin Chemical compound [Sn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F RBGLVWCAGPITBS-UHFFFAOYSA-L 0.000 claims description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 3
- 239000000386 donor Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 238000011160 research Methods 0.000 claims description 3
- 125000005630 sialyl group Chemical group 0.000 claims description 3
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 3
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 claims description 3
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- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 230000000397 acetylating effect Effects 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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- 229920006395 saturated elastomer Polymers 0.000 description 4
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- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical group N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 238000002360 preparation method Methods 0.000 description 3
- XYKIUTSFQGXHOW-UHFFFAOYSA-N propan-2-one;toluene Chemical compound CC(C)=O.CC1=CC=CC=C1 XYKIUTSFQGXHOW-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- 238000003786 synthesis reaction Methods 0.000 description 3
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- 229930186217 Glycolipid Natural products 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 125000003047 N-acetyl group Chemical group 0.000 description 2
- OVRNDRQMDRJTHS-KEWYIRBNSA-N N-acetyl-D-galactosamine Chemical group CC(=O)N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O OVRNDRQMDRJTHS-KEWYIRBNSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DRUIESSIVFYOMK-UHFFFAOYSA-N Trichloroacetonitrile Chemical compound ClC(Cl)(Cl)C#N DRUIESSIVFYOMK-UHFFFAOYSA-N 0.000 description 2
- KBGAYAKRZNYFFG-BOHATCBPSA-N aceneuramic acid Chemical group OC(=O)C(=O)C[C@H](O)[C@@H](NC(=O)C)[C@@H](O)[C@H](O)[C@H](O)CO KBGAYAKRZNYFFG-BOHATCBPSA-N 0.000 description 2
- YFHNDHXQDJQEEE-UHFFFAOYSA-N acetic acid;hydrazine Chemical compound NN.CC(O)=O YFHNDHXQDJQEEE-UHFFFAOYSA-N 0.000 description 2
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Lock And Its Accessories (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Catalysts (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/602580 | 1996-02-16 | ||
| US08/602,580 US5756695A (en) | 1996-02-16 | 1996-02-16 | Methods of synthesizing GM2 |
| PCT/US1997/001944 WO1997030061A1 (en) | 1996-02-16 | 1997-02-05 | Methods of synthesizing gm2 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU1858697A AU1858697A (en) | 1997-09-02 |
| AU712149B2 true AU712149B2 (en) | 1999-10-28 |
Family
ID=24411928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU18586/97A Ceased AU712149B2 (en) | 1996-02-16 | 1997-02-05 | Methods of synthesizing GM2 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5756695A (enExample) |
| EP (1) | EP0821691B1 (enExample) |
| JP (2) | JP3220704B2 (enExample) |
| AT (1) | ATE246697T1 (enExample) |
| AU (1) | AU712149B2 (enExample) |
| CA (1) | CA2217708A1 (enExample) |
| DE (1) | DE69723926T2 (enExample) |
| WO (1) | WO1997030061A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5977329A (en) * | 1996-02-16 | 1999-11-02 | Ludwig Institute For Cancer Research | Methods of synthesizing GM3 |
| US5951317A (en) * | 1998-04-13 | 1999-09-14 | Motorola, Inc. | Accessory connector assembly |
| CN1300158C (zh) * | 2005-03-22 | 2007-02-14 | 重庆邮电学院 | 一类非天然活性寡糖类化合物及其制备方法和应用 |
| WO2011053614A1 (en) * | 2009-10-30 | 2011-05-05 | Merck Sharp & Dohme Corp. | Crystalline cdm-nag and methods for producing same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0508493A1 (en) * | 1986-08-06 | 1992-10-14 | Mect Corporation | Ganglioside related compounds and method of producing the same |
| US5371202A (en) * | 1991-02-28 | 1994-12-06 | The Nisshin Oil Mills, Ltd. | Processes of preparing sialoglycosyl compounds |
-
1996
- 1996-02-16 US US08/602,580 patent/US5756695A/en not_active Expired - Fee Related
-
1997
- 1997-02-05 EP EP97904258A patent/EP0821691B1/en not_active Expired - Lifetime
- 1997-02-05 CA CA002217708A patent/CA2217708A1/en not_active Abandoned
- 1997-02-05 JP JP52939897A patent/JP3220704B2/ja not_active Expired - Fee Related
- 1997-02-05 DE DE69723926T patent/DE69723926T2/de not_active Expired - Fee Related
- 1997-02-05 AU AU18586/97A patent/AU712149B2/en not_active Ceased
- 1997-02-05 WO PCT/US1997/001944 patent/WO1997030061A1/en not_active Ceased
- 1997-02-05 AT AT97904258T patent/ATE246697T1/de not_active IP Right Cessation
-
2001
- 2001-05-16 JP JP2001145749A patent/JP2001316397A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0821691B1 (en) | 2003-08-06 |
| JPH11504348A (ja) | 1999-04-20 |
| US5756695A (en) | 1998-05-26 |
| EP0821691A4 (en) | 2001-10-04 |
| DE69723926T2 (de) | 2004-07-15 |
| JP3220704B2 (ja) | 2001-10-22 |
| AU1858697A (en) | 1997-09-02 |
| DE69723926D1 (de) | 2003-09-11 |
| WO1997030061A1 (en) | 1997-08-21 |
| JP2001316397A (ja) | 2001-11-13 |
| CA2217708A1 (en) | 1997-08-21 |
| ATE246697T1 (de) | 2003-08-15 |
| EP0821691A1 (en) | 1998-02-04 |
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