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Protected tetrasaccharides, their process of preparation and their use as transglucosylase acceptor substrates in chemo-enzymatic synthesis of shigella flexneri specific oligosaccharides

A glucose-based, protected technology for use in the field of O-antigen fragments

Pending Publication Date: 2020-04-17
INST PASTEUR +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the partially divergent character of this method, it only provides accessibility to a limited number of targets

Method used

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  • Protected tetrasaccharides, their process of preparation and their use as transglucosylase acceptor substrates in chemo-enzymatic synthesis of shigella flexneri specific oligosaccharides
  • Protected tetrasaccharides, their process of preparation and their use as transglucosylase acceptor substrates in chemo-enzymatic synthesis of shigella flexneri specific oligosaccharides
  • Protected tetrasaccharides, their process of preparation and their use as transglucosylase acceptor substrates in chemo-enzymatic synthesis of shigella flexneri specific oligosaccharides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0442] Embodiment 1: the synthesis of formula (I) compound

[0443] Synthesis of common precursors of A, B and C residues (1)

[0444] Allyl 4-O-(2-naphthylmethyl)-α-L-rhamnopyranoside (1)

[0445]

[0446] Acetyl chloride (50 mL, 0.70 mol, 2.5 equiv) was added dropwise to allyl alcohol (610 mL) at 0 °C, the solution was stirred for 25 min, and then L-rhamnose monohydrate (50 g, 277 mmol) was added. The mixture was heated at 70 °C for 2.5 h, then at 40 °C for 15 h. TLC (DCM / MeOH 8:2) trace showed complete conversion of the starting hemiacetal (Rf 0.2) to the less polar product (Rf 0.7). Cool the bath temperature to 0 °C, and by adding NaHCO 3 (102.5 g) to neutralize the solution. The suspension was passed through Pad filtered, evaporated solvent and co-evaporated 3 times with toluene.

[0447] The brown oily residue was dissolved in anhydrous acetone (300 mL), then 2,2-dimethoxypropane (100 mL, 0.81 mol, 3.0 eq) and PTSA (3.04 g, 16 mmol, 0.05 eq) were added sequen...

Embodiment 2

[0570] Example 2: Enzymatic α-D-glucosylation of Compounds of Formula (I) with Branched Sucrase enzyme

[0571] Table 1 shows some enzymes used in the context of the present invention.

[0572]

[0573]

[0574]

[0575] * Mutations are given relative to the sequence of GBD-CD2 wild type.

[0576] The sequence of the enzyme is as follows:

[0577] SEQ ID NO:1(BRS-E)

[0578] SEQ ID NO:2(BRS-A)

[0579] SEQ ID NO:3(BRS-B-D1)

[0580] SEQ ID NO:4(BRS-B-D2)

[0581] SEQ ID NO:5(BRS-C)

[0582] SEQ ID NO:6(BRS-D)

[0583] SEQ ID NO: 7 (GBD-CD2).

[0584]

[0585]

[0586]

[0587]

[0588]

[0589] Table 2 shows some mutants of BRS-B-D2 used in the context of the present invention.

[0590]

[0591]

[0592]

[0593]

[0594]

[0595]

[0596] Isolation of the brsE gene

[0597] The brsE gene was identified in the Leuconostoc mesenteris KFRI-MG genome (NCBI reference sequence: CP000574) by nucleotide BLAST of the GH70α-transgluc...

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Abstract

The present invention provides protected tetrasaccharides, their process of preparation and their use in the synthesis of oligosaccharides, in particular fragments of O-antigens from Shigella flexneri, for example of serotype la, lb, 2a, 2b, 3a, X, 4a, 4b, 5a, 5b, 7a or 7b.

Description

technical field [0001] The present invention provides protected tetrasaccharides, methods for their preparation, and their presence in oligosaccharides (particularly from O-antigen fragments of Shigella flexneri, such as serotypes 1a, 1b, 2a, 2b, 3a, Use in the synthesis of X, 4a, 4b, 5a, 5b, 7a or 7b). Background technique [0002] Carbohydrates displayed on the surface of cells and pathogens have enormous therapeutic potential. On the one hand, the human glycome is being studied in detail, and on the other hand, the increasing knowledge of microbial carbohydrates and carbohydrate-binding proteins offers new opportunities for therapeutic and preventive interventions. Carbohydrates are actively studied as vaccine components in a variety of applications. In this context, synthetic carbohydrates represent an attractive alternative to carbohydrate antigens of biological origin. more than ten years ago, approval to demonstrate feasibility. Other vaccine candidates derived ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/00C07H15/10C12P19/12C12P19/26
CPCC07H15/00C07H15/10C12P19/04C12P19/14C12P19/28C12P19/18C07H15/203C07H13/04
Inventor L·米拉尔G·勒海格特Z·胡L·A·巴雷尔I·安德烈C·穆利斯M·勒莫-西梅翁S·巴尔贝M·本科欧罗彻A·本伊梅达杜尔尼
Owner INST PASTEUR
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