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Enzymatic preparation method of oligosaccharide Lewis X

A technology for catalytic preparation and oligosaccharides, which is applied in the field of preparation of lewis X -GlcNAc), can solve the problems of low yield and not suitable for large-scale production, and achieve the effect of low yield

Inactive Publication Date: 2013-03-27
GLYCSYN BIOTECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the synthetic method yield is very low, is not suitable for large-scale production

Method used

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  • Enzymatic preparation method of oligosaccharide Lewis X

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Embodiment Construction

[0015] The present invention will be described in detail below through specific embodiments, but the present invention is not limited to these examples per se.

[0016] One, the preparation of compound 3:

[0017] L-fucose (compound 2, 4.0 g, 24.4 mmol) was dissolved in pyridine (50 mL), and phenylacetyl chloride (17.2 g, 122 mmol) was slowly added dropwise under stirring, and the reaction was stirred overnight at room temperature. After the reaction was detected by TLC, the mixture was poured into ice water, diluted with dichloromethane (100 mL), washed with hydrochloric acid (4 N) and saturated sodium bicarbonate solution, and the organic phase was dried with anhydrous magnesium sulfate and concentrated to obtain compound syrup Compound 3 (15 g).

[0018] Two, the preparation of compound 4:

[0019] The above crude product was dissolved in acetic acid (16 mL), cooled in an ice bath, hydrogen bromide in acetic acid solution (16 mL) was added, and the mixture was stirred and...

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Abstract

The invention relates to an enzymatic preparation method of oligosaccharide compounds, in particular to a preparation method of lewis X (Gal-Beta-1, 4-(Fuc-Alpha-1, 3)-GlcNAc). The sialic acid derivative SLe<x> of the compound lewis X (Gal-Beta-1, 4-(Fuc-Alpha-1, 3)-GlcNAc) is terminal oligosaccharide of glycolipid and glycoprotein on cell surfaces and plays a critical role in mutual recognition of cells. The enzymatic preparation method comprises the following steps: with L-fucose as a raw material, carrying out protection and 1-bit phosphorylation on the L-fucose, and making the phosphorylated L-fucose to react with GMP-morpholine ester to generate general donor GDP-L-fucose of the fucose; and making the GDP-L-fucose to react with N-acetylated galactosamine under the action of alpha-1, 3-fucose transferase to obtain Lewis X. The enzymatic preparation method disclosed by the invention is simple and convenient in process and achieves the purpose of preparing triglycan Lewis X which is prepared by taking simple and easily-obtained sugar as the raw material in a stereospecificity manner by means of the action of the transferase.

Description

technical field [0001] The present invention relates to the enzyme-catalyzed preparation method of oligosaccharide compound, specifically the preparation method of lewis X (Gal-β-1,4-(Fuc-α-1,3)-GlcNAc); the sialic acid of the compound Derivative SLe x It is a terminal oligosaccharide of glycolipids and glycoproteins on the cell surface, and plays a vital role in the recognition of cell interactions. Background technique [0002] Lewis X is a fucosylated trisaccharide antigen widely distributed on the cell surface of eukaryotes and some bacteria. It is a glycan with multiple functions and plays an important role in many physiological and pathological processes. For example, sialylated Lewis X, a tetrasaccharide expressed in white blood cells such as granulocytes and monocytes, is closely associated with a variety of tumors including pancreatic, breast, colon, and lung cancers. Glycans containing Lewis X are also found in the infectious bacterium Helicobacter pylori and the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/18
Inventor 胡天顺林海平
Owner GLYCSYN BIOTECH