CN115368485A - High-efficiency synthesis method of lentinan core fragment-lentinan - Google Patents

High-efficiency synthesis method of lentinan core fragment-lentinan Download PDF

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CN115368485A
CN115368485A CN202211156182.2A CN202211156182A CN115368485A CN 115368485 A CN115368485 A CN 115368485A CN 202211156182 A CN202211156182 A CN 202211156182A CN 115368485 A CN115368485 A CN 115368485A
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trisaccharide
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袁婷婷
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    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
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Abstract

The invention relates to a high-efficiency preparation method of lentinan hexaose with bioactivity, in particular to a core fragment beta- (1 → 6) branched chain beta- (1 → 3) main chain of lentinan which can be used as an anti-tumor medicament. The preparation method comprises the steps of firstly preparing a disaccharide acceptor connected with 1-6, coupling the monosaccharide donor and the disaccharide acceptor under the action of Lewis acid to obtain a module intermediate namely a trisaccharide donor, removing a trisaccharide benzyl serving as the trisaccharide acceptor, coupling the trisaccharide donor and the trisaccharide donor under the action of Lewis acid to obtain hexaose, removing a protecting group to obtain the lentinus edodes hexaose, and similarly synthesizing the lentinus edodes nonaose.

Description

High-efficiency synthesis method of lentinan core fragment-lentinan
Technical Field
The invention relates to a high-efficiency synthesis method of lentinan, which is a core fragment of lentinan and has biological activity, and particularly can be used as an anti-tumor agent.
Background
Many fungal polysaccharides, such as lentinan (from lentinan, lentinus edodes), grifolan (from Grifola frondosa), schizophyllan (from Schizophyllum commune), and pachyman (from Poria cocos), have anti-tumor activity and are now receiving increasing attention.
Modern researches have shown that the antitumor activity of polysaccharide is mainly acted by the immune system of human body rather than directly inhibiting the growth of tumor cells, so that the polysaccharide antitumor drug has much less toxic and side effects on human body than other antitumor drugs. Lentinan is a specific immunological adjuvant with thymus-dependent T cell targeting and macrophage participation. It can identify the macrophages of antigens in spleen and liver, promote the production of lymphocyte activating factor, release various auxiliary T cell factors, and enhance the phagocytosis rate of host abdominal cavity macrophages, and after host body injects lentinan for several hours, the levels of some serum factors with physiological activity, such as acute phase protein induction factor, vasodilation and bleeding induction factor, IL-1 generation induction factor, IL3 and colony stimulating factor reach the peak value. These factors, acting on lymphocytes, hepatocytes, vascular endothelial cells, generate a number of potent immune responses, which lead to the maturation, differentiation, proliferation and peripheral release of precursor T cells within the thymus. The common structural feature of these polysaccharides with biological activity is the glucan oligosaccharide containing beta- (1 → 6) branched chain beta- (1 → 3) main chain. These polysaccharides are mostly derived from lentinan, a lentinan polysaccharide of Lentinus edodes. However, like most of the naturally extracted polysaccharides, lentinan (lentinan) cannot be obtained in very high purity and the molecular weight is often uncertain, thus greatly affecting its clinical application.
The lentinan core fragment beta- (1 → 6) branched chain beta- (1 → 3) lentinan hexaose and lentinan nonaose of the main chain are prepared by adopting a synthesis mode with extremely simple route, convenient operation and high efficiency, and the lentinan hexaose and the lentinan nonaose obtained by the chemical method have the advantages of high purity, high yield and controllable quality. At present, chemical preparation methods of hexasaccharide and heptasaccharide are reported, but the reaction operability is complex, the operation is difficult, the intermediate post-treatment is complex, the reaction is easy to fail when impurities are contained, the requirements on technical personnel are extremely high, and the industrialization cannot be realized. The method provided by the patent has the advantages of simple reaction synthetic route, strong selectivity, high raw material utilization rate, low technical requirement on operators, high yield and suitability for industrialization.
Disclosure of Invention
The invention aims to provide a synthetic method which has a simple route, is convenient to operate and is efficient, so as to synthesize lentinus edodes hexaose and lentinus edodes nonaose which have biological activity and can be particularly used as an antitumor beta- (1 → 6) branched chain beta- (1 → 3) main chain.
The purpose of the invention is realized by the following steps: taking 2-O-benzoyl-3-O-benzyl-thioethyl glucose 1 as a glycosyl acceptor, taking 4, 6-benzylidene-2, 3-di-O-benzoyl-thioethyl glucose 3 as a glycosyl donor, coupling under the action of TMSOTf to obtain disaccharide 4, removing benzyl to obtain disaccharide acceptor 5, protecting 2-O-benzoyl-3-O-benzyl-thioethyl glucose 1 with benzoyl to obtain 2,4, 6-tri-O-benzoyl-3-O-benzyl-thioethyl glucose 2 as a monosaccharide donor, and obtaining trisaccharide donor 6 by taking monosaccharide donor 2 and disaccharide acceptor 5 under the action of TMSOTf.
The trisaccharide donor 6 is debenzylated to obtain the trisaccharide acceptor 7.
The trisaccharide donor 6 and the trisaccharide acceptor 7 are coupled under the action of TMSOTf and NIS to obtain hexaose 8, the hexaose 9 is obtained after the benzyl group is removed, and then all the protecting groups are removed to obtain the target product of lentinus edodes hexaose 10.
Hexasaccharide 8 is used as glycosyl donor, is coupled with trisaccharide acceptor 7 under the action of TMSOTf and NIS to obtain nonasaccharide 11, the benzyl group is removed to obtain nonasaccharide 12, and then all protecting groups are removed to obtain the target lentinus edodes nonasaccharide 13.
The synthesis method of the invention comprises the following steps:
(1) 1 mol of 2-O-benzoyl-3-O-benzyl-thioethyl glucose 1 is taken as a glycosyl acceptor, 1.2 mol of 4, 6-benzylidene-2, 3-di-O-benzoyl-thioethyl glucose 3 is taken as a glycosyl donor, coupling is carried out under the action of TMSOTf to obtain disaccharide 4, debenzylation is carried out to obtain a disaccharide acceptor 5, 2-O-benzoyl-3-O-benzyl-thioethyl glucose 1 is protected by benzoyl to obtain 2,4, 6-tri-O-benzoyl-3-O-benzyl-thioethyl glucose 2 is taken as a monosaccharide donor, and 1.2 mol of monosaccharide donor 2 and 1 mol of disaccharide acceptor 5 are taken as a trisaccharide donor 6 under the action of TMSOTf. As shown in the following formula:
bz is: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-;
Figure 807583DEST_PATH_IMAGE001
Figure DEST_PATH_IMAGE002
(2) Trisaccharide donor 6 in Pd (OH) 2 And removing benzyl under the action of-C and formic acid to obtain the trisaccharide acceptor 7. As shown in the following formula:
bz is as follows: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-;
Figure DEST_PATH_IMAGE003
(3) 2 mol of trisaccharide donor 6 and 1 mol of trisaccharide acceptor 7 are coupled under the action of TMSOTf and NIS to obtain hexasaccharide 8 in Pd (OH) 2 Removing benzyl under the action of-C and formic acid to obtain hexaose 9, and removing all protecting groups to obtain the target product lentinus edodes hexaose 10. As shown in the following formula:
bz is: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-;
Figure DEST_PATH_IMAGE004
(4) 2 mol of hexasaccharide 8 is taken as glycosyl donor, and is coupled with 1 mol of trisaccharide acceptor 7 under the action of TMSOTf and NIS to obtain nonasaccharide 11, the benzyl group is removed to obtain nonasaccharide 12, and then all protecting groups are removed to obtain the target lentinus edodes nonasaccharide 13. As shown in the following formula:
bz is: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-;
Figure DEST_PATH_IMAGE005
The present invention relates to a high-effective synthesis method of lentinan hexaose and lentinan nonaose which have biological activity and can be used as core fragment of lentinan for resisting tumor.
Detailed Description
The technical solutions of the present invention are described below with specific examples, but the scope of the present invention is not limited thereto.
Examples
Preparation of trisaccharide donor 6
(1) 2-O-benzoyl-3-O-benzyl-thioethyl glucose 1 (2.17 g, 5 mmol) was dissolved in 15 ml of DMF, triethylamine (1.67 ml, 12 mmol) was added, benzoyl chloride (1.39 ml, 12 mmol) was added dropwise in an ice bath, after stirring at 60 ℃ for 6 hours, thin layer chromatography analysis showed that the reaction was complete, 30 ml of dichloromethane was added to the reaction system, and then washed with saturated sodium bicarbonate (25 ml. Times.2) and saturated sodium chloride (25 ml. Times.1) in this order, the organic phase was collected, the solvent was evaporated under reduced pressure, and 2,4, 6-tri-O-benzoyl-3-O-benzyl-thioethyl glucose 2 was obtained after benzoyl protection in 98.6% yield.
(2) Monosaccharide 1 (4.33 g, 10 mmol) was dissolved in 20 ml dichloromethane to give solution a, monosaccharide 3 (6.25 g, 12 mmol) was dissolved in 25 ml dichloromethane to give solution B, a and B were mixed to give solution C, TMSOTf (580 μ l, 5 mmol) was added to C, a 4 a molecular sieve was added, and after 4 hours of reaction at 25 ℃, thin layer chromatography analysis indicated that the reaction was complete. Suction filtration and evaporation of the solvent under reduced pressure gave disaccharide 4 in 95.4% yield.
(3) Disaccharide 4 (4.90 g, 5.5 mmol) was dissolved in 50 ml tetrahydrofuran: methanol (V: V9 2 -C (20 wt%, 0.4 g) and 88% formic acid (1.6 ml, 44 mmol), stirring for 10 min at 25 ℃ and TLC analysis indicated that the reaction was complete, filtration, washing with 100 ml methanol and evaporation to dryness gave the disaccharide acceptor 5 in 98.3% yield.
(4) Monosaccharide 2 (7.69 g, 12 mmol) was dissolved in 30 ml dichloromethane to give solution D, disaccharide acceptor 5 (8.02 g, 10 mmol) was dissolved in 30 ml dichloromethane to give solution E, D and E were mixed to give solution F, TMSOTf (580 μ l, 5 mmol) was added to F, a 4 a molecular sieve was added and after 8 hours reaction at 25 ℃, thin layer chromatography analysis indicated that the reaction was complete. And (3) carrying out suction filtration, decompressing and distilling off the solvent to obtain the trisaccharide donor 6, separating by adopting column chromatography, eluting by using ethyl acetate/cyclohexane (1/3) as eluent, and collecting corresponding components to obtain the pure trisaccharide donor 6, wherein the yield is 93.9%.
Preparation of trisaccharide acceptor 7
Trisaccharide donor 6 (6.91 g, 5 mmol) was dissolved in 50 ml tetrahydrofuran: methanol (V: V9 2 C (20 wt%, 0.4 g) and 88% formic acid (1.6 ml, 44 mmol), stirred at 25 ℃ for 10 minutes, TLC analysis indicated completion of the reaction, filtered, washed with 100 ml of methanol and evaporated to dryness to give the trisaccharide acceptor 7 in 94.3% yield.
Preparation of lentinus edodes hexasaccharide 10
(1) The trisaccharide donor 6 (27.62 g, 20 mmol) was dissolved in 100 ml dichloromethane to give solution a, the trisaccharide acceptor 7 (12.91 g, 10 mmol) was dissolved in 50 ml dichloromethane to give solution B, a and B were mixed to give solution C, TMSOTf (690 μ l, 6 mmol), NIS (0.65 ml, 6 mmol) were added to C, and 4 a molecular sieve was added, and after 8 hours of reaction at 25 ℃, thin layer chromatography analysis indicated that the reaction was complete. Vacuum filtering, distilling off solvent under reduced pressure, separating by column chromatography, eluting with ethyl acetate/cyclohexane (1.5/1) as eluent, and collecting corresponding components to obtain hexasaccharide 8 with a yield of 96.6%.
(2) Hexasaccharide 8 (26.09 g, 10 mmol) was dissolved in 100 ml tetrahydrofuran: methanol (V: V9 2 -C (20 wt%, 0.8 g) and 88% formic acid (3.2 ml, 88 mmol), stirring for 15 minutes at 25 ℃, tlc analysis showed the reaction was complete, filtering, washing with 200 ml methanol and evaporation to dryness gave the hexasaccharide 9 in 92.5% yield.
(3) Hexasaccharide 9 (25.19 g, 10 mmol) was dissolved in 90 ml of methanol, acetyl chloride (0.07 ml, 1 mmol) was added dropwise first, after 2.5 hours at 25 ℃ and potassium carbonate (2.76 g, 20 mmol) was added slowly, after 24 hours at 25 ℃ thin layer chromatography analysis indicated that the reaction was complete, concentratedPure lentinan hexaose 10 is obtained by separating the condensed glucan gel LH-20 (methanol) column, and the yield is 97.4%. And (2) MS:990.4 [ M +1 ]] - 。
Preparation of mushroom nine sugar 13
(1) Hexasaccharide donor 8 (52.18 g, 20 mmol) was dissolved in 200 ml dichloromethane to give solution a, trisaccharide acceptor 7 (12.91 g, 10 mmol) was dissolved in 50 ml dichloromethane to give solution B, a and B were mixed to give solution C, TMSOTf (690 μ l, 6 mmol), NIS (0.65 ml, 6 mmol) were added to C, and 4 a molecular sieve was added and after 12 hours reaction at 25 ℃, thin layer chromatography analysis indicated that the reaction was complete. Vacuum filtering, distilling off solvent under reduced pressure, separating by column chromatography, eluting with ethyl acetate/cyclohexane (2.5/1) as eluent, and collecting corresponding components to obtain nonaose 11 with yield of 90.4%.
(2) Nonasaccharide 11 (30.70 g, 8 mmol) was dissolved in 150 ml tetrahydrofuran: methanol (V: V9 2 -C (20 wt%, 0.8 g) and 88% formic acid (3.2 ml, 88 mmol), stirring for 30 minutes at 25 ℃, tlc analysis showed the reaction was complete, filtering, washing with 300 ml methanol and evaporation to dryness to give the nonaose 12 in 93.5% yield.
(3) Nine sugar 12 (37.78 g, 10 mmol) was dissolved in 130 ml methanol, acetyl chloride (0.07 ml, 1 mmol) was added dropwise first, after 2 hours at 25 ℃, potassium carbonate (2.76 g, 20 mmol) was added slowly, after 30 hours at 25 ℃, thin layer chromatography analysis showed the reaction was complete, and pure lentinan nine 13 was isolated on sephadex LH-20 (methanol) column after concentration in 95.7% yield. And (2) MS:1477.3 [ M +1 ]] - 。
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited by the above examples, and any other modifications without departing from the scope of the present invention should be replaced by equivalents, and all such modifications are included in the scope of the present invention.

Claims (5)

1. The efficient synthesis process of lentinan core segment-lentinan hexaose with beta- (1 → 6) branched chain beta- (1 → 3) main chain features that 1-6 connected disaccharide acceptor is first prepared, monosaccharide donor and disaccharide acceptor are coupled under the action of Lewis acid to obtain the body-trisaccharide donor in the module, the trisaccharide eliminating benzyl is used as the trisaccharide acceptor, and the trisaccharide donor is coupled under the action of Lewis acid to obtain hexaose, and the protecting group is eliminated to obtain lentinan hexaose.
2. The process of claim 1, wherein the trisaccharide donor is prepared by: taking 2-O-benzoyl-3-O-benzyl-thioethyl glucose 1 as a glycosyl acceptor, taking 4, 6-benzylidene-2, 3-di-O-benzoyl-thioethyl glucose 3 as a glycosyl donor, coupling under the action of TMSOTf to obtain disaccharide 4, removing benzyl to obtain disaccharide acceptor 5, taking 2-O-benzoyl-3-O-benzyl-thioethyl glucose 1 protected by benzoyl to obtain 2,4, 6-tri-O-benzoyl-3-O-benzyl-thioethyl glucose 2 as a monosaccharide donor, and taking monosaccharide donor 2 and disaccharide acceptor 5 under the action of TMSOTf to obtain trisaccharide donor 6, wherein the formula is shown as follows:
bz is: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-。
Figure 644672DEST_PATH_IMAGE001
Figure 194733DEST_PATH_IMAGE002
3. The method of claim 1, wherein the trisaccharide acceptor is prepared by: the trisaccharide donor 6 is debenzylated to obtain the trisaccharide acceptor 7, which is shown as the following formula:
bz is: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-。
Figure 780436DEST_PATH_IMAGE003
4. The lentinan of claim 1, which is prepared by: the trisaccharide donor 6 and the trisaccharide acceptor 7 are coupled under the action of TMSOTf and NIS to obtain hexaose 8, the benzyl group is removed to obtain hexaose 9, and then all protecting groups are removed to obtain a target product, namely lentinus edodes hexaose 10, which is shown as the following formula:
bz is: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-。
Figure 210280DEST_PATH_IMAGE004
5. The preparation method of the mushroom nonaose as described in claim 1, comprising: namely, hexaose 8 is taken as glycosyl donor, is coupled with trisaccharide acceptor 7 under the action of TMSOTf and NIS to obtain nonaose 11, is subjected to benzyl removal to obtain nonaose 12, and is subjected to all protecting groups removal to obtain target lentinus edodes nonaose 13, wherein the formula is shown as follows:
bz is as follows: c 6 H 5 (C = O) -; bn is C 6 H 5 CH 2 -; ph is C 6 H 5 -; SEt is C 2 H 5 S-。
Figure 264955DEST_PATH_IMAGE005
CN202211156182.2A 2022-09-22 2022-09-22 High-efficiency synthesis method of lentinan core fragment-lentinan Pending CN115368485A (en)

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