CN107417810B - The synthetic method of AntiHIV1 RT activity double activated sulfonic group bagasse xylan ferrocenecarboxylic acid ester - Google Patents
The synthetic method of AntiHIV1 RT activity double activated sulfonic group bagasse xylan ferrocenecarboxylic acid ester Download PDFInfo
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- C08B37/0057—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Xylans, i.e. xylosaccharide, e.g. arabinoxylan, arabinofuronan, pentosans; (beta-1,3)(beta-1,4)-D-Xylans, e.g. rhodymenans; Hemicellulose; Derivatives thereof
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Abstract
The invention discloses a kind of synthetic methods of AntiHIV1 RT activity double activated sulfonic group bagasse xylan ferrocenecarboxylic acid ester.Using bagasse xylan as raw material, using NaNO2‑NaHSO3The amino sodium trisulfonate of Aqueous phase synthesis is esterifying agent, under alkaline condition, synthesizes bagasse xylan sulfate by catalyst of ZSM-5；Ferrocene formyl chloride is prepared as raw material in dichloromethane solvent using ferrocenecarboxylic acid again, continue using ferrocene formyl chloride as second step esterifying agent, triethylamine is catalyst, carries out secondary esterification with bagasse xylan sulfate in dichloromethane solvent to synthesize the sulfonic group bagasse xylan ferrocenecarboxylic acid ester with AntiHIV1 RT activity double activated.Products therefrom of the present invention combines the HIV-resistant activity of sulfonic group and bagasse xylan after double catalytic esterification modifying and decoratings, and the performances such as thermal stability, HIV-resistant activity, bacteriostatic activity for having ferrocene group, foundation is provided for the further development and application of inverase.
Description
Technical field
The present invention relates to technical field of polymer materials, especially a kind of AntiHIV1 RT activity double activated sulfonic group bagasse xylan two
The synthetic method of ferrocenemonocarboxylic acid ester.
Background technique
Xylan is that one kind is environmentally protective, natural reserves are big, abundance biomass resource.As a kind of the big of complexity
Molecular substance, due to the uniqueness of its structure, so that it is with different activity against organisms such as AntiHIV1 RT activity, anticancer, antiviral, anti-
Oxidation, antibacterial etc. are widely used in the fields such as medicine, biology.As that studies xylan gos deep into, in order to overcome its water solubility
Difference, bioactivity itself the defect such as low, people start to explore by changing side-chain radical or introducing in xylan backbone
The activity against organisms of xylan improve in new functional group.
In recent years, domestic and international researcher mainly carries out the mono-esterification of xylan such as xylan sulfuric ester, acetic acid esters
Research.The study found that xylan sulfuric ester has the effects that AntiHIV1 RT activity, anticoagulation, antiviral, drop blood ester.But xylan list
The defects such as that there are still activity against organisms is low for esterification derivative, degree of substitution is low.Thus, consider the base in xylan monoesterified derivatives
Other active groups are introduced on plinth to further enhance the bioactivity of xylan.Macromolecule polyalcohol containing ferrocene group
Draw with attributes such as unique three-dimensional structure, high molecular weight, membrane permeability, abnormal metabolism and high-melting-points, and by ferrocene group
Enter into biopolymer macromolecular can be improved the bioactivity such as its antibacterial, AntiHIV1 RT activity, anticancer.Thus expectation is in xylan sulfuric acid
Ferrocene group is introduced on the basis of ester, further increases the HIV-resistant activity of xylan.
The present invention is using bagasse xylan as raw material, and amino sodium trisulfonate is esterifying agent, under aqueous basic conditions first
Synthesize bagasse xylan sulfate, the active esterifying agent being then esterified using ferrocenecarboxylic acid as second step, in dichloromethane solvent
It is middle that a kind of sulfonic group bagasse xylan ferrocenecarboxylic acid ester with AntiHIV1 RT activity double activated is made through catalysis reaction.
Summary of the invention
The purpose of the invention is to improve the HIV-resistant activity of bagasse xylan, a kind of AntiHIV1 RT activity double activated sulfonic group is provided
The synthetic method of bagasse xylan ferrocenecarboxylic acid ester.
Specific steps are as follows:
(1) bagasse xylan is placed in 60 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains butt bagasse wood
Glycan.
(2) it weighs 0.75~2.0g sodium nitrite and is dissolved in 10~25mL distilled water obtaining sodium nitrite in aqueous solution.
(3) 3.5~8.0g sodium hydrogensulfite, 10~30mL distilled water is taken to be added in the four-hole boiling flask of 250mL, it will under stirring
System is warming up to 70~90 DEG C.Sodium nitrite in aqueous solution obtained by the step (2) being placed in constant pressure funnel is slowly added dropwise to body
In system, control is added dropwise in 30~50 minutes, and the reaction was continued 1.5~2 hours.
(4) temperature of system obtained by step (3) is down to 40~50 DEG C, the sodium hydroxide solution for being 0.5mol/L with concentration
Regulation system pH is 8~9 up to amino sodium trisulfonate esterifying agent.
(5) it weighs 1.5~3.0g of butt bagasse xylan obtained by step (1) and is added to amino trisulfonic acid obtained by step (4)
In sodium solution, 0.1~0.25g ZSM-5 molecular sieve catalyst is added, temperature is maintained to react 4~6 hours under conditions of 50 DEG C.
(6) step (5) resulting material is poured into 100mL beaker, the hydrochloric acid solution that concentration is 0.5mol/L is added dropwise and adjusts
PH is 6~7, until there is Precipitation, stands 40~60 minutes.
(7) step (6) resulting material is filtered, and respectively with pure dehydrated alcohol washing precipitate 2~3 times of 15~20mL analysis
It is sent into 50 DEG C of vacuum constant temperature drying box afterwards and dries 24 hours to constant weight to get bagasse xylan sulfate.
(8) it takes 0.4~0.8g ferrocenecarboxylic acid to be added in the four-hole boiling flask of 250mL, and point of 5~10mL is added thereto
Absolute dichloromethane is analysed, is stirred 30 minutes under conditions of 5~20 DEG C.
(9) the pure oxalyl chloride of the analysis of 4~8mL is taken, the analysis absolute dichloromethane of 10~20mL is dissolved in, is placed in constant pressure funnel
In, it is slowly dropped in reaction system obtained by step (8), control is added dropwise in 30~60 minutes, and it is 2~3 small that the reaction was continued
When.
(10) 0.05~0.2mL is added dropwise into reaction system obtained by step (9) and analyzes pure pyridine, it is 8~10 small that the reaction was continued
When.
(11) it will be revolved in flask that step (10) resulting material is placed in Rotary Evaporators under conditions of 20~30 DEG C
Turn evaporation, nitrogen is passed through after removing, and dissolved with the analysis absolute dichloromethane of 15~25mL.
(12) 0.8~1.5g of bagasse xylan sulfate obtained by step (7) is taken to be added in system obtained by step (11), and
0.15~0.4mL is added thereto and analyzes pure triethylamine, is stirred to react under conditions of 30~40 DEG C 3~4 hours, then cools down
Continue to be stirred to react 1~2 hour under conditions of to 20~30 DEG C.
(13) step (12) resulting material is filtered, and is sent after washing 3 times with the analysis pure acetone of 15~25mL respectively to 50
DEG C thermostatic drying chamber in dry 24 hours to constant weight to get product sulfonic group bagasse xylan ferrocenecarboxylic acid ester.
(14) BaCl is used2Double activated sulfonic group bagasse xylan two obtained in Turbidity of Gelatin method determination step (13)
The sulfate group degree of substitution of ferrocenemonocarboxylic acid ester.The calculation formula of sulfate group degree of substitution DS are as follows:
In formula:
132 --- the relative molecular mass of xylose units in bagasse xylan molecule；
102 --- 1 hydroxyl in polysaccharide molecule becomes-OSO after being substituted3Na, the value added of relative molecular mass；
32 --- the relative atomic mass of S；
S% --- the mass percentage of element sulphur in sample.
(15) using double activated sulfonic group bagasse xylan ferrocene first obtained in determination of acid-basetitration step (14)
The ferrocene acyl substitution of acid esters.Specific method and steps are as follows: accurately weighing in about 0.5g sample merging 50mL conical flask,
10mL distilled water is added, shakes up, the phenolphthalein indicator of 2 drops 5% is added, is titrated with the NaOH standard solution that concentration is 0.1mol/L
It (will not fade in 30s) to light red.The NaOH standard solution that 2.5mL concentration is 0.5mol/L is added with pipette again, shakes up,
Sealing, at room temperature concussion saponification 4 hours.Be titrated to later with the hydrochloric acid standard solution that concentration is 0.5mol/L it is colourless, as
Titration end-point.Ferrocene acyl substitution (DSC) calculating formula it is as follows:
In formula:
The mass fraction of w-sulfonic group bagasse xylan ferrocenecarboxylic acid ester ferrocenyl formyl, %；
V0- titration bagasse xylan consumes hydrochloric acid standard solution volume, Unit/mL；
V1The hydrochloric acid standard solution volume of-titration bagasse xylan ferrocenecarboxylic acid ester consumption, Unit/mL；
CHCl- hydrochloric acid standard solution concentration, unit mol/L；
M-bagasse xylan ferrocenecarboxylic acid ester sample quality, unit g；
The relative molecular mass of 230 and 132-ferrocenyl formyls and bagasse xylan dehydration xylose units.
The present invention is first with NaNO2-NaHSO3Aqueous phase carrys out synthesizing amino sodium trisulfonate esterifying agent, in an aqueous medium will
Bagasse xylan and amino sodium trisulfonate esterification obtain bagasse xylan sulfate, with ferrocenecarboxylic acid are again then esterification
Agent carries out second step catalytic esterification, obtained product sulfonic group with bagasse xylan sulfate in dichloromethane solvent
Bagasse xylan ferrocenecarboxylic acid ester is a kind of composite modified derivative of AntiHIV1 RT activity xylan of double activated.Resulting target product
The HIV-resistant activity that sulfonic group and bagasse xylan are not only combined after double catalytic esterification modifying and decoratings has been provided simultaneously with two cyclopentadienyls
The performances such as thermal stability, HIV-resistant activity, the bacteriostatic activity of iron-based group, for inverase further development and application provide according to
According to.
Detailed description of the invention
Fig. 1 is that the IR of bagasse xylan schemes.
Fig. 2 is the IR of the sulfonic group bagasse xylan ferrocenecarboxylic acid ester of the AntiHIV1 RT activity double activated of preparation of the embodiment of the present invention
Figure.
Fig. 3 is that the SEM of bagasse xylan schemes.
Fig. 4 is the SEM of the sulfonic group bagasse xylan ferrocenecarboxylic acid ester of the AntiHIV1 RT activity double activated of preparation of the embodiment of the present invention
Figure.
Fig. 5 is the XRD diagram of bagasse xylan.
Fig. 6 is the XRD of the sulfonic group bagasse xylan ferrocenecarboxylic acid ester of the AntiHIV1 RT activity double activated of preparation of the embodiment of the present invention
Figure.
Fig. 7 is that the TG-DTG of bagasse xylan schemes.
Fig. 8 is the TG- of the sulfonic group bagasse xylan ferrocenecarboxylic acid ester of the AntiHIV1 RT activity double activated of preparation of the embodiment of the present invention
DTG figure.
Specific embodiment
Embodiment:
(1) bagasse xylan is placed in 60 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains butt bagasse wood
Glycan.
(2) it weighs 0.75g sodium nitrite and is dissolved in 10mL distilled water obtaining sodium nitrite in aqueous solution.
(3) it takes 3.5g sodium hydrogensulfite, 10mL distilled water to be added in the four-hole boiling flask of 250mL, system heats up under stirring
To 90 DEG C.Sodium nitrite in aqueous solution obtained by the step (2) being placed in constant pressure funnel is slowly added dropwise into system, controls 30
It is added dropwise in minute, the reaction was continued 1.5 hours.
(4) temperature of system obtained by step (3) is down to 50 DEG C, is adjusted with the sodium hydroxide solution that concentration is 0.5mol/L
System pH is about 9 up to amino sodium trisulfonate esterifying agent.
(5) it weighs butt bagasse xylan 1.5g obtained by step (1) and is added to amino sodium trisulfonate solution obtained by step (4)
In, 0.15g ZSM-5 molecular sieve catalyst is added, temperature is maintained to react 4 hours under conditions of 50 DEG C.
(6) step (5) resulting material is poured into 100mL beaker, the hydrochloric acid solution that concentration is 0.5mol/L is added dropwise and adjusts
PH is about 7, until there is Precipitation, stands 40 minutes.
(7) step (6) resulting material is filtered, and is sent into after analyzing pure dehydrated alcohol washing precipitate 3 times with 15mL respectively
24 hours are dried in 50 DEG C of vacuum constant temperature drying box to constant weight to get bagasse xylan sulfate.
(8) it takes 0.46g ferrocenecarboxylic acid to be added in the four-hole boiling flask of 250mL, and the pure dichloro of analysis of 5mL is added thereto
Methane stirs 30 minutes under conditions of 10 DEG C.
(9) the pure oxalyl chloride of the analysis of 4mL is taken, the analysis absolute dichloromethane of 10mL is dissolved in, is placed in constant pressure funnel, is slowly dripped
It is added in reaction system obtained by step (8), control is added dropwise in 60 minutes, and the reaction was continued 2 hours.
(10) 0.05mL is added dropwise into reaction system obtained by step (9) and analyzes pure pyridine, the reaction was continued 10 hours.
(11) rotation steaming will be carried out in flask that step (10) resulting material is placed in Rotary Evaporators under conditions of 20 DEG C
Hair is passed through nitrogen, and is dissolved with the analysis absolute dichloromethane of 15mL after removing.
(12) bagasse xylan sulfate 0.85g obtained by step (7) is taken to be added in system obtained by step (11), and to its
Middle addition 0.20mL analyzes pure triethylamine, is stirred to react under conditions of 35 DEG C 3 hours, under conditions of being then cooled to 25 DEG C after
It is continuous to be stirred to react 2 hours.
(13) step (12) resulting material is filtered, and is sent after washing 3 times with the analysis pure acetone of 15mL respectively to 50 DEG C
24 hours are dried in thermostatic drying chamber to constant weight to get product sulfonic group bagasse xylan ferrocenecarboxylic acid ester.
(14) BaCl is used2Turbidity of Gelatin method carries out the measurement of Sulfation degree of substitution to products therefrom in step (7), obtains
Its degree of substitution is 1.19.
(15) ferrocenecarboxylic acid esterification degree of substitution measurement is carried out to step (13) products therefrom using acid-base titration, obtains it
Degree of substitution is 0.129.
Product is analyzed through IR, in 1120.57cm-1And 617.41cm-1There is the feature stretching vibration absworption peak of S=O,
1654.69cm-1Place is C=O stretching vibration, 1093.04cm-1Place is the characteristic absorption peak of C-O-C, 1108.66cm-1With
1004.89cm-1For VC-CThe characteristic absorption peak of (luxuriant ring), in 489.13cm-1Place be C-Fe characteristic absorption peak, illustrate sulfuric acid and
Ferrocenecarboxylic acid is esterified successfully bagasse xylan.Product after XRD analysis esterification modification 15.7277 °, 17.5105 °,
Occur strong diffraction maximum at 17.6891 °, 19.7571 °, 25.1262 °, shows crystallinity height, crystalline content is more, and crystal region ratio
It is more complete.Sem analysis is results showed that double esterification surface is reunited together, and there is no unformed parts, and shape is more
Be intended to circle, and surface irregularity, there is obviously gap and damaged rill, it was demonstrated that after over-churning original structure by
It destroys.The TG-DTG curve of double esterification product is analyzed, 150~250 DEG C of stages, mass loss reaches up to 30%, 670
The loss amount in~700 DEG C of this stages is about 10%, and cause loss may be some groups in carboxylate agent.
Claims (1)
1. a kind of synthetic method of sulfonic group bagasse xylan ferrocenecarboxylic acid ester, it is characterised in that specific steps are as follows:
(1) bagasse xylan is placed in 60 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains butt bagasse xylan；
(2) it weighs 0.75 ~ 2.0g sodium nitrite and is dissolved in 10 ~ 25mL distilled water obtaining sodium nitrite in aqueous solution；
(3) 3.5 ~ 8.0g sodium hydrogensulfite, 10 ~ 30mL distilled water is taken to be added in the four-hole boiling flask of 250mL, by system liter under stirring
Temperature is to 70 ~ 90 DEG C；Sodium nitrite in aqueous solution obtained by the step (2) being placed in constant pressure funnel is slowly added dropwise into system, control
System is added dropwise in 30 ~ 50 minutes, and the reaction was continued 1.5 ~ 2 hours；
(4) temperature of system obtained by step (3) is down to 40 ~ 50 DEG C, is adjusted with the sodium hydroxide solution that concentration is 0.5mol/L
System pH is 8 ~ 9 up to amino sodium trisulfonate esterifying agent；
(5) it weighs 1.5 ~ 3.0g of butt bagasse xylan obtained by step (1) and is added to amino sodium trisulfonate solution obtained by step (4)
In, 0.1 ~ 0.25g ZSM-5 molecular sieve catalyst is added, temperature is maintained to react 4 ~ 6 hours under conditions of 50 DEG C；
(6) step (5) resulting material is poured into 100mL beaker, it is 6 that the hydrochloric acid solution that concentration is 0.5mol/L, which is added dropwise, and adjusts pH
~ 7, until there is Precipitation, stand 40 ~ 60 minutes；
(7) step (6) resulting material is filtered, and is sent into after analyzing pure dehydrated alcohol washing precipitate 2 ~ 3 times with 15 ~ 20mL respectively
24 hours are dried in 50 DEG C of vacuum constant temperature drying box to constant weight to get bagasse xylan sulfate；
(8) it takes 0.4 ~ 0.8g ferrocenecarboxylic acid to be added in the four-hole boiling flask of 250mL, and the analysis pure two of 5 ~ 10mL is added thereto
Chloromethanes stirs 30 minutes under conditions of 5 ~ 20 DEG C；
(9) the pure oxalyl chloride of the analysis of 4 ~ 8mL is taken, the analysis absolute dichloromethane of 10 ~ 20mL is dissolved in, is placed in constant pressure funnel, slowly
It is added drop-wise in reaction system obtained by step (8), control is added dropwise in 30 ~ 60 minutes, and the reaction was continued 2 ~ 3 hours；
(10) 0.05 ~ 0.2mL is added dropwise into reaction system obtained by step (9) and analyzes pure pyridine, the reaction was continued 8 ~ 10 hours；
(11) rotation steaming will be carried out in flask that step (10) resulting material is placed in Rotary Evaporators under conditions of 20 ~ 30 DEG C
Hair is passed through nitrogen, and is dissolved with the analysis absolute dichloromethane of 15 ~ 25mL after removing；
(12) 0.8 ~ 1.5g of bagasse xylan sulfate obtained by step (7) is taken to be added in system obtained by step (11), and to its
0.15 ~ 0.4mL of middle addition analyzes pure triethylamine, is stirred to react 3 ~ 4 hours under conditions of 30 ~ 40 DEG C, is then cooled to 20 ~ 30
Continue to be stirred to react 1 ~ 2 hour under conditions of DEG C；
(13) step (12) resulting material is filtered, and is sent after washing 3 times with the analysis pure acetone of 15 ~ 25mL respectively to 50 DEG C of perseverance
24 hours are dried in warm drying box to constant weight to get product sulfonic group bagasse xylan ferrocenecarboxylic acid ester.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102875698A (en) * | 2012-10-30 | 2013-01-16 | 桂林理工大学 | Method for synthesizing bagasse xylan sulfate by sodium aminotrisulfonate water-phase esterification process |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102875698A (en) * | 2012-10-30 | 2013-01-16 | 桂林理工大学 | Method for synthesizing bagasse xylan sulfate by sodium aminotrisulfonate water-phase esterification process |
Non-Patent Citations (1)
| Title |
|---|
| "Synthesis, crystal structure, electronic spectroscopy, electrochemistry and biological studies of carbohydrate containing ferrocene amides";Rajiv Trivedi等;《Applied Organometallic Chemistry》;20121231;第26卷;第369-376页 * |
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Application publication date: 20171201 Assignee: Guilin Qi Hong Technology Co.,Ltd. Assignor: GUILIN University OF TECHNOLOGY Contract record no.: X2022450000103 Denomination of invention: Synthesis of Anti HIV Double Active Sulfonic Acid Bagasse Xylan Ferrocenyl Formate Granted publication date: 20191126 License type: Common License Record date: 20221121 |