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Method for synthesizing beta-D glucose(1->3)alpha-L rhamnose(1-3)alpha-L rhamnose(1-3)alpha-L rhamnose

A technology of rhamnose and glucose, which is applied in the field of synthesis of β-D glucose α-L rhamnose α-L rhamnose α-L rhamnose, can solve the problems of complicated synthesis process and achieve simplified reaction steps , easy operation and short reaction route

Inactive Publication Date: 2011-10-12
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2010, Prashant Ranjan Verma et al. (Prashant Ranjan Verma; Balaram Mukhopadhyay. Synthesis of a tetrasaccharide related to the O-antigen from Azospirillum lipoferum SR65[J].Carbohydrate Research, 2010, 345: 432-436.) synthesized β-D Glucose (1→3)α-L rhamnose (1→3)α-L rhamnose (1→3)α-L rhamnose, however, more protective groups are used in its synthesis, making the whole The synthesis process is cumbersome

Method used

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  • Method for synthesizing beta-D glucose(1->3)alpha-L rhamnose(1-3)alpha-L rhamnose(1-3)alpha-L rhamnose
  • Method for synthesizing beta-D glucose(1->3)alpha-L rhamnose(1-3)alpha-L rhamnose(1-3)alpha-L rhamnose
  • Method for synthesizing beta-D glucose(1->3)alpha-L rhamnose(1-3)alpha-L rhamnose(1-3)alpha-L rhamnose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Synthesis of monosaccharide receptor 1

[0029] L-rhamnose (3.28g, 20mmol) was dissolved in 75ml of dry allyl alcohol, and boron trifluoride ether (BF 3 ·OEt 2 ) (2.8ml, 10mmol), heated to 90℃~95℃ under reflux, reacted for 5~7 hours, cooled, neutralized the reaction solution with triethylamine to pH=6.8~7.2, concentrated and then column chromatography (petroleum ether: acetic acid Ethyl ester 1:20) to obtain 13.060 g of monosaccharide acceptor, with a yield of 75%.

Embodiment 2

[0030] Example 2 Synthesis of Monosaccharide Donor 2

[0031] At 0℃, to acetic anhydride (AC 2 O) (9.35ml, 100mmol) was added dropwise perchloric acid (81μL, 1mmol) to the solution. After stirring for half an hour at 0℃, L-rhamnose (1.64g, 10mmol) was added to the mixed solution and stirred at 0℃ After 2 hours, the reaction was quenched by adding ice water. Use CH 2 Cl 2 Extraction, organic phase with saturated NaHCO 3 The excess acid was neutralized, concentrated under reduced pressure and dissolved in DMF (3ml). Ammonium acetate (0.15g, 20mmol) was added and reacted for 12 hours. The mixture was extracted with water and ethyl acetate, and the organic phase was concentrated and separated by column chromatography (petroleum ether: ethyl acetate 3:1) to obtain monosaccharide receptor 2 (2.262 g) with a yield of 78%.

Embodiment 3

[0032] Example 3 Synthesis of Monosaccharide Donor 6

[0033] At 0℃, to acetic anhydride (AC 2 O) (9.35ml, 100mmol) was added dropwise perchloric acid (81μL, 1mmol) to the solution, after stirring at 0℃ for half an hour, glucose (1.8g, 10mmol) was added to the mixture, stirring at 0℃ for 2 hours before adding Ice water quenches the reaction. Use CH 2 Cl 2 Extraction, organic phase with saturated NaHCO 3 The excess acid was neutralized, concentrated under reduced pressure and dissolved in DMF (3ml). Ammonium acetate (0.15g, 20mmol) was added and reacted for 12 hours. Extract with a mixture of water and ethyl acetate, concentrate the organic phase, and separate by column chromatography (petroleum ether: ethyl acetate 3:1) to obtain monosaccharide receptor 6 (2.565 g) with a yield of 75%.

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Abstract

The invention provides a method for synthesizing beta-D glucose(1->3)alpha-L rhamnose(1->3)alpha-L rhamnose(1->3)alpha-L rhamnose. The method comprises the following steps of: obtaining 1,3-alpha-connection disaccharides and 1,3-beta-connection disaccharides by trichloroacetimidate of acyl rhamnose and acyl glucose serving as a glycosyl donor and 1-O-allyl rhamnose serving as a glycosyl acceptor; coupling the 1,3-alpha-connection disaccharides serving as a glycosyl acceptor and the 1,3-beta-connection disaccharides serving as a glycosyl donor to obtain tetrasaccharides; and removing the protection to obtain the beta-D glucose(1->3)alpha-L rhamnose(1->3)alpha-L rhamnose(1->3)alpha-L rhamnose.

Description

Technical field [0001] The present invention relates to biological activity, in particular to β-D glucose (1→3)α-L rhamnose (1→3)α-L rhamnose (1→3)α- which is related to biological nitrogen fixation. Synthesis method of L rhamnose. Background technique [0002] At present, the use of chemical fertilizers is increasing and soil fertility is declining. How to maintain a good cycle of agricultural ecological environment has become a major issue in modern agriculture in the world. Under this background, the joint nitrogen fixation of the rhizosphere has gradually shown its special significance. Combined nitrogen fixation is widespread in nature, and in-depth research and discussion of this system is of great significance for developing the nitrogen fixation potential of non-legumes. [0003] 2008 Yuliya P. Fedonenko et al. (Yuliya P. Fedonenko; Evelina L. Zdorovenko; Svetlana A. Konnova; Vadim V. Kachala; Vladimir V. Ignatov. Structural analysis of the O-antigen of the lipopolysacchar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H3/08C07H1/00
CPCY02P20/55
Inventor 朱玉亮徐松杨雷雷王军
Owner NANJING UNIV OF TECH
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