Title:
CHEMICAL SYNTHESIS METHOD OF CHITOSAN OLIGOSACCHARIDE WITH CONTROLLABLE POLYMERIZATION DEGREE
Document Type and Number:
WIPO Patent Application WO/2023/147789
Kind Code:
A1
Abstract:
Disclosed in the present invention is a chemical synthesis method of chitosan oligosaccharide with a controllable polymerization degree, which belongs to the field of sugar chemistry. The method of the present invention comprises the following steps: (1) using a monosaccharide building block which is connected with an activatable leaving group on an anomeric carbon and contains a C-4 exposed hydroxyl as a substrate, so that the monosaccharide building block is used as both a donor and a receptor; adding an accelerant to carry out a glycosylation reaction, so as to generate chitosan oligosaccharide derivatives with different polymerization degrees; and changing the protection groups of the saccharide building block and the glycosylation reaction conditions to generate fully-protected chitosan oligosaccharide derivatives with different polymerization degrees; and (2) performing deprotection to obtain corresponding chitosan oligosaccharides. The method of the present invention has the advantages of a controllable polymerization degree, simple and convenient steps and a high conversion rate.
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Inventors:
YIN JIAN (CN)
CHENG DAOQUAN (CN)
ZOU XIAOPENG (CN)
WANG XIANGCHUAN (CN)
HU JING (CN)
LIU HAIYU (CN)
PENG XIAOJUN (CN)
WANG CHENG (CN)
TIAN GUANGZONG (CN)
WANG DIANHAI (CN)
CHENG DAOQUAN (CN)
ZOU XIAOPENG (CN)
WANG XIANGCHUAN (CN)
HU JING (CN)
LIU HAIYU (CN)
PENG XIAOJUN (CN)
WANG CHENG (CN)
TIAN GUANGZONG (CN)
WANG DIANHAI (CN)
Application Number:
PCT/CN2023/079441
Publication Date:
August 10, 2023
Filing Date:
March 03, 2023
Export Citation:
Assignee:
SHANDONG JINGBO AGROCHEMICALS TECH CO LTD (CN)
UNIV JIANGNAN (CN)
UNIV JIANGNAN (CN)
International Classes:
C07H3/06; C07H1/00; C07H3/02
Foreign References:
| CN106432539A | 2017-02-22 | |||
| CN1696141A | 2005-11-16 | |||
| CN115215910A | 2022-10-21 | |||
| CN101421287A | 2009-04-29 | |||
| CN101168550A | 2008-04-30 | |||
| CN113004348A | 2021-06-22 | |||
| CN113402569A | 2021-09-17 |
Other References:
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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
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
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
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
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
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
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
Attorney, Agent or Firm:
SHANDONG QIZHI INTELLECTUAL PROPERTY AGENCY LTD. (CN)
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