PT100073A - Processo para a preparacao estereo-selectiva de beta-fucopiranosil-fosfatos e de guanosina-difosfato-fucose muito pura - Google Patents

Processo para a preparacao estereo-selectiva de beta-fucopiranosil-fosfatos e de guanosina-difosfato-fucose muito pura Download PDF

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Publication number
PT100073A
PT100073A PT100073A PT10007392A PT100073A PT 100073 A PT100073 A PT 100073A PT 100073 A PT100073 A PT 100073A PT 10007392 A PT10007392 A PT 10007392A PT 100073 A PT100073 A PT 100073A
Authority
PT
Portugal
Prior art keywords
fucose
fucopyranosyl
beta
process according
phosphate
Prior art date
Application number
PT100073A
Other languages
English (en)
Inventor
Willy Kinzy
Richard R Schmidt
Karl-Heinz Jung
Barbara Wegmann
Jurgen Hemberger
Original Assignee
Merck Patent Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh
Publication of PT100073A publication Critical patent/PT100073A/pt

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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
    • 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

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  • 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)

Claims (1)

  1. 24
    REIVINDICAÇÕES: la. Processo para a preparação estéreo-selectiva de beta-L fucopiranosil-fosfatos, caracterizado pelo facto de se transformar L-fucose protegida nas posições 2, 3 e 4 no correspondente 0-(alfa-L-fucopiranosil)-tricloroaceti-midato, se fazer reagir este com um fosfato orgânico absolutamente isento de ácido de fórmula geral PO (OH) (OR) 2 na qual R significa alquilo em C^-C^, fenilo ou benzilo, se eliminar o radical R do grupo fosfato e os grupos de protecção no anel de fucopiranosilo e se isolar o beta-L-fucopiranosil fosfato sob a forma de sal. 2a. Processo de acordo com a reivindicação 1, caracterizado pelo facto de, como grupos de protecção, se empregar acetilo ou benzilo. 3a. Processo de acordo com as reivindicações 1 ou 2, caracterizado pelo facto de se fazer reagir selectivamente a L-fucose protegida com hidreto de sódio de maneira a obter-se o correspondente alfa-tricloroacetimidato. 4a. Processo de acordo com uma qualquer das reivindicações 1 a 3, caracterizado pelo facto de se preparar 2,3,4-tri-O-acetil-L-fucose a partir de L-fucose tetracetilado numa reacção numa única operação. 5a. Processo de acordo com a reivindicação 4, caracterizado pelo facto de se eliminar o grupo acetilo anomérico da tetra-O-acetil L-fucose com acetato de hidrazina. % 4 r W
    6a. Processo para a preparação estéreo-selectiva de guanosina-difosfato-fucose (GDP-fucose) muito pura, caracterizado pelo facto de se transformar beta-L- fucopiranosil-fosfato num sal facilmente soluvél, se fazer reagir este com guanosina monofosfato (GMP) activado e se purificar a GDP-fucose assim formada por meio de cromatografia em fase liquida sob alta pressão (HPLC) preparação com um sistema tampão facilmente evaporável como eluente. 7a. Processo de acordo com a reivindicação 6, caracterizado pelo facto de se transformar beta-L- fucopiranosil-fosfato no sal de tri-u-octilamónio. 8a. Processo de acordo com as reivindicações 6 ou 7, caracterizado pelo facto de, como GMP activado, se empregar GMP-morfolidato. 9a. Processo de acordo com uma qualquer das reivindicações 6 ou 8, caracterizado pelo facto de, como eluente para a purificação preparativa, se empregar hidrogenocarbonato de trietilamónio. 10a. Processo para a preparação de GDP-fucose de acordo com uma qualquer das reivindicações 6 a 9, caracterizado pelo facto de o beta-L-fucopiranosil-fosfato ser preparado de acordo com uma qualquer das reivindicações 1 a 5. Lisboa, 30 de Janeiro de 1992 /o Agente Oficial da Propriedade Industrial AMÉRICO DA SILVA CARVALHO Agente Oficial de Propriedade Industrial Rua Marquês de Fronteira. N.· 127 - 2.° 1000 LISBOA
PT100073A 1991-01-31 1992-01-30 Processo para a preparacao estereo-selectiva de beta-fucopiranosil-fosfatos e de guanosina-difosfato-fucose muito pura PT100073A (pt)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
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
PT100073A true PT100073A (pt) 1993-03-31

Family

ID=6424052

Family Applications (1)

Application Number Title Priority Date Filing Date
PT100073A PT100073A (pt) 1991-01-31 1992-01-30 Processo para a preparacao estereo-selectiva de beta-fucopiranosil-fosfatos e de guanosina-difosfato-fucose muito pura

Country Status (14)

Country Link
US (1) US5371203A (pt)
EP (1) EP0502298A3 (pt)
JP (1) JPH04312598A (pt)
KR (1) KR920014823A (pt)
AU (1) AU653383B2 (pt)
CA (1) CA2060283A1 (pt)
CS (1) CS27092A3 (pt)
DE (1) DE4102817A1 (pt)
HU (1) HUT61316A (pt)
IE (1) IE920313A1 (pt)
MX (1) MX9200375A (pt)
PT (1) PT100073A (pt)
TW (1) TW206233B (pt)
ZA (1) ZA92720B (pt)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
AU653383B2 (en) 1994-09-29
ZA92720B (en) 1992-12-30
EP0502298A2 (de) 1992-09-09
KR920014823A (ko) 1992-08-25
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 (pt) 1993-05-21
DE4102817A1 (de) 1992-08-06
JPH04312598A (ja) 1992-11-04
CS27092A3 (en) 1992-08-12
AU1054092A (en) 1992-08-06

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Effective date: 19921110

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Effective date: 19990317