Title:
NON-NATURAL SUGAR, AND SYNTHESIS METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2024/087806
Kind Code:
A1
Abstract:
Disclosed in the present invention are a non-natural sugar, and a synthesis method therefor and the use thereof. The synthesis method comprises: subjecting a hydroxyl group of an amino sugar to per-trimethylsilane protection at room temperature, selectively exposing an amino group on the sugar, and coupling and converting the amino group at room temperature to obtain a per-trimethylsilane-protected non-natural sugar with an orthogonal group; and removing a trimethylsilane protecting group from the per-trimethylsilane-protected non-natural sugar with an orthogonal group to obtain a non-natural sugar without a protecting group. The present invention takes the advantages of existing non-natural sugars into consideration, such that not only is it ensured that the non-natural sugar can be efficiently utilized by cells, but an S side reaction of the non-natural sugar with cysteine in protein during the metabolic process thereof is also effectively avoided; in addition, efficient metabolic marking is achieved. In a cell test, the usage concentration of a 1,6-diacylated non-natural sugar is one order of magnitude lower than that of the non-natural sugar without a protecting group.
Inventors:
CHEN XING (CN)
CHENG BO (CN)
CHENG BO (CN)
Application Number:
PCT/CN2023/112917
Publication Date:
May 02, 2024
Filing Date:
August 14, 2023
Export Citation:
Assignee:
UNIV BEIJING (CN)
International Classes:
C07H5/06; C07H13/04; C07H13/06; C12Q1/02
Foreign References:
| CN115677798A | 2023-02-03 | |||
| CN116217638A | 2023-06-06 | |||
| CN102993256A | 2013-03-27 | |||
| CN104177451A | 2014-12-03 |
Other References:
BO CHENG: "Facile Synthesis of Clickable Unnatural Sugars in the Unprotected and 1,6‐Di‐ O ‐Acylated Forms for Metabolic Glycan Labeling", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 29, no. 11, 21 February 2023 (2023-02-21), DE, XP093162767, ISSN: 0947-6539, DOI: 10.1002/chem.202203054
KE QIN: "Protein S-Glyco-Modification through an Elimination–Addition Mechanism", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 142, no. 20, 20 May 2020 (2020-05-20), pages 9382 - 9388, XP093162770, ISSN: 0002-7863, DOI: 10.1021/jacs.0c02110
WELDAY DESTA WELDU: "Selective Acetylation of Non-anomeric Groups of per- O -Trimethylsilylated Sugars", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 7, 2 April 2021 (2021-04-02), pages 5336 - 5344, XP093162773, ISSN: 0022-3263, DOI: 10.1021/acs.joc.0c02813
KE QIN: "Protein S-Glyco-Modification through an Elimination–Addition Mechanism", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 142, no. 20, 20 May 2020 (2020-05-20), pages 9382 - 9388, XP093162770, ISSN: 0002-7863, DOI: 10.1021/jacs.0c02110
WELDAY DESTA WELDU: "Selective Acetylation of Non-anomeric Groups of per- O -Trimethylsilylated Sugars", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 7, 2 April 2021 (2021-04-02), pages 5336 - 5344, XP093162773, ISSN: 0022-3263, DOI: 10.1021/acs.joc.0c02813
Attorney, Agent or Firm:
LIAN & LIEN IP ATTORNEYS (CN)
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