Ganglioside GM3 and/or analogue thereof, synthesis method and application of ganglioside GM3 and/or analogue thereof

A technology of gangliosides and synthetic methods, which is applied in the field of organic compound synthesis, and can solve problems such as undiscovered patent publications

Inactive Publication Date: 2020-06-05
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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[0006] Through the search, no patent publications related to

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  • Ganglioside GM3 and/or analogue thereof, synthesis method and application of ganglioside GM3 and/or analogue thereof
  • Ganglioside GM3 and/or analogue thereof, synthesis method and application of ganglioside GM3 and/or analogue thereof
  • Ganglioside GM3 and/or analogue thereof, synthesis method and application of ganglioside GM3 and/or analogue thereof

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Embodiment Construction

[0084] The embodiments of the present invention will be described in detail below. It should be noted that the embodiments are illustrative, not restrictive, and cannot limit the protection scope of the present invention.

[0085] The raw materials used in the present invention, unless otherwise specified, are conventional commercially available products; the methods used in the present invention, unless otherwise specified, are conventional methods in the art.

[0086] A ganglioside GM3 and / or its analogue, its structural formula is as follows:

[0087]

[0088] in:

[0089] R 2 , selected from fluorine atom, hydrogen atom, azide, hydroxyl, acetyl, trimethylacetyl;

[0090] R 3 , selected from fluorine atom, hydrogen atom, acetyl group, hydroxyl group;

[0091] R 4 , selected from fluorine atom, hydrogen atom, acetyl group, hydroxyl group;

[0092] R 7 , selected from nitrogen acetamide, nitrogen propionyl amino, nitrogen trifluoroacetamide, nitrogen azidoacetamide;...

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Abstract

The invention relates to a method for synthesizing ganglioside GM3 and/or an analogue thereof. The method includes the following steps: (1) selecting a lactose donor represented by a general formula Iand/or an analogue thereof and selecting a sphingosine derivative represented by a general formula II; (2) synthesizing lactosphingosine and/or a derivative thereof from the compounds shown in the general formula I and the general formula II by using a glycosidation reaction, and then removing a protecting group; (3) synthesizing sialylated lactosphingosine and/or derivative thereof by using a one-pot three-enzyme method; and (4) carrying out condensation reaction on the general formula IV and a fatty acid to synthesize the ganglioside GM3 and/or analogue thereof. The method can be used for efficiently, rapidly and simply synthesizing ganglioside GM3 and analogues thereof. The method adopts a chemical enzymatic method, can be applied in preparing ganglioside GM3 and analogues thereof, andcan be used for drug development.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, in particular to ganglioside GM3 and / or its analogue, synthesis method and application. Background technique [0002] Ganglioside GM3 is the earliest discovered ganglioside with the simplest structure. Yamakawa et al. (Yamakawa, T.; Suzuki, S.J. Biochem. 1952, 39, 393) first isolated it from horse red blood cells in 1952. NeuNAcα(2-3)Galβ(1-4)Glcβ(1-3)Cer can be formed by linking a molecule of sialic acid with lactosylceramide (LacCer, Lactosylceramide) under the action of GM3 synthetase. The sugar chain of GM3 can be further extended to form ganglioside compounds. Ganglioside GM3 has important biological functions, such as maintaining the stability of cell membrane structure; as a cell surface marker and antigen, participating in cell-cell interaction and recognition; as a differentiation marker, participating in cell growth regulation and information transmission; as a certa...

Claims

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Application Information

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IPC IPC(8): C07H15/10C07H1/06C12P19/44
CPCC07H15/10C07H1/06C12P19/44Y02P20/55
Inventor 孟欣李晓李婷申张慧明
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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