WO2023147789A1 - Procédé de synthèse chimique d'oligosaccharide de chitosane à degré de polymérisation contrôlable - Google Patents
Procédé de synthèse chimique d'oligosaccharide de chitosane à degré de polymérisation contrôlable Download PDFInfo
- Publication number
- WO2023147789A1 WO2023147789A1 PCT/CN2023/079441 CN2023079441W WO2023147789A1 WO 2023147789 A1 WO2023147789 A1 WO 2023147789A1 CN 2023079441 W CN2023079441 W CN 2023079441W WO 2023147789 A1 WO2023147789 A1 WO 2023147789A1
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- WO
- WIPO (PCT)
- Prior art keywords
- chemical synthesis
- synthesis method
- self
- glycosylation reaction
- reaction
- Prior art date
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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- 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
- C07H3/02—Monosaccharides
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- 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
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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)
Abstract
La présente invention divulgue un procédé de synthèse chimique d'oligosaccharide de chitosane ayant un degré de polymérisation contrôlable, qui se rapporte au domaine de la chimie du sucre. Le procédé selon la présente invention consiste : (1) à utiliser un bloc de construction de monosaccharide qui est relié à un groupe partant activable sur un carbone anomère et contient un hydroxyle exposé à C-4 en tant que substrat, de sorte que le bloc de construction de monosaccharide est utilisé à la fois en tant que donneur et récepteur ; à ajouter un accélérateur pour effectuer une réaction de glycosylation, de façon à générer des dérivés d'oligosaccharide de chitosane ayant différents degrés de polymérisation ; et à changer les groupes de protection du bloc de construction de saccharide et les conditions de réaction de glycosylation pour générer des dérivés d'oligosaccharide de chitosane entièrement protégés avec différents degrés de polymérisation ; et (2) à effectuer une déprotection pour obtenir des oligosaccharides de chitosane correspondants. Le procédé selon la présente invention présente les avantages suivants : un degré de polymérisation contrôlable, des étapes simples et pratiques et un taux de conversion élevé.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CN202210252687.2A CN115215910A (zh) | 2022-03-15 | 2022-03-15 | 一种聚合度可控的壳寡糖化学合成方法 |
CN202210252687.2 | 2022-03-15 |
Publications (1)
Publication Number | Publication Date |
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WO2023147789A1 true WO2023147789A1 (fr) | 2023-08-10 |
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PCT/CN2023/079441 WO2023147789A1 (fr) | 2022-03-15 | 2023-03-03 | Procédé de synthèse chimique d'oligosaccharide de chitosane à degré de polymérisation contrôlable |
Country Status (2)
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CN (1) | CN115215910A (fr) |
WO (1) | WO2023147789A1 (fr) |
Families Citing this family (1)
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CN115215910A (zh) * | 2022-03-15 | 2022-10-21 | 京博农化科技有限公司 | 一种聚合度可控的壳寡糖化学合成方法 |
Citations (6)
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CN1696141A (zh) * | 2003-12-22 | 2005-11-16 | 叶新山 | 一种寡糖的合成方法 |
CN101168550A (zh) * | 2006-10-25 | 2008-04-30 | 中国科学院大连化学物理研究所 | 一种氨基葡萄糖四糖的合成方法 |
CN101421287A (zh) * | 2006-04-07 | 2009-04-29 | 纳幕尔杜邦公司 | 脂壳寡糖的化学合成方法 |
CN106432539A (zh) * | 2016-07-28 | 2017-02-22 | 河南科技学院 | 一种壳聚糖接枝芳香酚衍生物及其制备方法和应用 |
CN113004348A (zh) * | 2021-03-26 | 2021-06-22 | 南京工业大学 | 一种机械自组装制备低聚糖的方法 |
CN115215910A (zh) * | 2022-03-15 | 2022-10-21 | 京博农化科技有限公司 | 一种聚合度可控的壳寡糖化学合成方法 |
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2022
- 2022-03-15 CN CN202210252687.2A patent/CN115215910A/zh active Pending
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2023
- 2023-03-03 WO PCT/CN2023/079441 patent/WO2023147789A1/fr unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1696141A (zh) * | 2003-12-22 | 2005-11-16 | 叶新山 | 一种寡糖的合成方法 |
CN101421287A (zh) * | 2006-04-07 | 2009-04-29 | 纳幕尔杜邦公司 | 脂壳寡糖的化学合成方法 |
CN101168550A (zh) * | 2006-10-25 | 2008-04-30 | 中国科学院大连化学物理研究所 | 一种氨基葡萄糖四糖的合成方法 |
CN106432539A (zh) * | 2016-07-28 | 2017-02-22 | 河南科技学院 | 一种壳聚糖接枝芳香酚衍生物及其制备方法和应用 |
CN113004348A (zh) * | 2021-03-26 | 2021-06-22 | 南京工业大学 | 一种机械自组装制备低聚糖的方法 |
CN113402569A (zh) * | 2021-03-26 | 2021-09-17 | 南京工业大学 | 一种机械自组装制备低聚糖的方法 |
CN115215910A (zh) * | 2022-03-15 | 2022-10-21 | 京博农化科技有限公司 | 一种聚合度可控的壳寡糖化学合成方法 |
Non-Patent Citations (6)
Title |
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CHENG CHENG-WEI, WU CHUNG-YI, HSU WEN-LIAN, WONG CHI-HUEY: "Programmable One-Pot Synthesis of Oligosaccharides", BIOCHEMISTRY, vol. 59, no. 34, 1 September 2020 (2020-09-01), pages 3078 - 3088, XP093082510, ISSN: 0006-2960, DOI: 10.1021/acs.biochem.9b00613 * |
DELBIANCO MARTINA, BHARATE PRIYA, VARELA-ARAMBURU SILVIA, SEEBERGER PETER H.: "Carbohydrates in Supramolecular Chemistry", CHEMICAL REVIEWS, AMERICAN CHEMICAL SOCIETY, US, vol. 116, no. 4, 24 February 2016 (2016-02-24), US , pages 1693 - 1752, XP093082515, ISSN: 0009-2665, DOI: 10.1021/acs.chemrev.5b00516 * |
SIGNE GRANN HANSEN; TROELS SKRYDSTRUP: "Studies Directed to the Synthesis of Oligochitosans – Preparation of Building Blocks and Their Evaluation in Glycosylation Studies", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, WILEY-VCH, DE, vol. 2007, no. 20, 11 May 2007 (2007-05-11), DE , pages 3392 - 3401, XP072108638, ISSN: 1434-193X, DOI: 10.1002/ejoc.200700048 * |
TOSHIKI NOKAMI ET AL.: "Automated Electrochemical Assembly of the Protected Potential TMG-chitotriomycin Precursor Based on Rational Optimization of the Carbohydrate Building Block", ORGANIC LETTERS, vol. 17, 10 March 2015 (2015-03-10), XP055734782, DOI: 10.1021/acs.orglett.5b00406 * |
TYRIKOS‐ERGAS THEODORE, BORDONI VITTORIO, FITTOLANI GIULIO, CHAUBE MANISHKUMAR A., GRAFMüLLER ANDREA, SEEBERGER PETER H: "Systematic Structural Characterization of Chitooligosaccharides Enabled by Automated Glycan Assembly", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 27, no. 7, 1 February 2021 (2021-02-01), DE, pages 2321 - 2325, XP055825611, ISSN: 0947-6539, DOI: 10.1002/chem.202005228 * |
ZHANG Z, ET AL.: "PROGRAMMABLE ONE-POT OLIGOSACCHARIDE SYNTHESIS", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 121, 1 January 1999 (1999-01-01), pages 734 - 753, XP001077048, ISSN: 0002-7863, DOI: 10.1021/ja982232s * |
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