CN106699597A - 一种α‑氰基‑4‑羟基肉桂酸（CHCA）与硅基介孔材料共价偶联基质的合成方法 - Google Patents
一种α‑氰基‑4‑羟基肉桂酸（CHCA）与硅基介孔材料共价偶联基质的合成方法 Download PDFInfo
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- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- G—PHYSICS
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
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- G01N27/64—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode using wave or particle radiation to ionise a gas, e.g. in an ionisation chamber
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Abstract
本发明的目的是针对常见基质CHCA在MALDI‑TOF MS小分子检测时背景干扰大的不足，提供一种CHCA与硅基介孔材料共价偶联的新基质，降低基质的背景干扰。反应采用活性酯法，硅基介孔材料表面首先修饰氨基，之后EDC活化CHCA羧基形成酰胺键，NHS取代EDC活化酯而形成NHS活化酯，再与硅基介孔材料表面的氨基结合，实现CHCA与硅基介孔材料的偶联。
Description
技术领域
本发明涉及一种新型基质辅助激光解吸电离(MALDI)基质的合成方法，具体涉及一种α-氰基-4-羟基肉桂酸(CHCA)与硅基介孔材料共价偶联基质的合成方法。
背景技术
基质辅助激光解吸电离飞行时间质谱(MALDI-TOF MS)是一种快速、高通量的软电离质谱技术，在蛋白质、多肽、寡核苷酸等物质的分析方面获得广泛应用。由于常用MALDI基质为小分子有机酸，因此在分析分子量小于500Da的小分子化合物时会引入大量的基质加合峰，干扰待测物信号。研究制备适于小分子(分子量＜500Da)检测的基质对进一步拓宽MALDI-TOF MS应用范围具有重要意义。
发明内容
本发明针对常见基质CHCA在MALDI-TOF MS小分子检测时背景干扰大的不足，提供一种CHCA与硅基介孔材料共价偶联的新基质，降低了基质的背景干扰。
本发明的技术方案概述如下：硅基介孔材料表面首先修饰氨基，之后CHCA表面羧基被EDC，NHS活化，与修饰氨基的硅基介孔材料共价结合，形成新型基质。
(1)配制10～100mg/mL的介孔材料悬浊液，超声辅助分散，溶剂为无水乙醇；
(2)按照3-氨丙基三乙氧基硅烷(APTES)：硅基介孔材料体积比0.5～3∶1的比例加入APTES，50～100℃水浴搅拌反应4～12小时；
(3)反应液2000r/min～10000r/min离心2～10min；依次用去离子水和无水乙醇洗涤3～5次；
(4)孔径为0.22μm以下的滤膜抽滤，滤膜截留的合成产物30～60℃真空干燥，制得硅基介孔材料@APTES；
(5)按照硅基介孔材料@APTES，CHCA，N-羟基丁二酰亚胺(NHS)，1-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐(EDC·HCl)质量比1∶1∶3～5∶12～20的比例混合，加入纯水使CHCA最终浓度为10～50mg/mL，避光条件下反应4h以上；
(6)纯水离心洗涤3次后，用乙腈洗涤，自然干燥备用。
附图说明
图1为α-氰基-4-羟基肉桂酸(CHCA)与硅基介孔材料共价偶联基质的合成路线示意图
具体实施方式
实施方案1
(1)称取0.5g SBA-15与50ml无水乙醇混合，超声混匀；
(2)加入100ml的APTES，在75℃水浴搅拌10h；
(3)3000r/min离心5min后，依次用纯水和无水乙醇洗3次后，0.22μm有机系滤膜抽滤；
(4)取抽滤后的合成产物50℃真空干燥，制得SBA-15@APTES；
(5)称取0.03gSBA-15@APTES、0.12gNHS、0.45gEDC、0.03gCHCA，加入1ml纯水混匀，避光条件下涡旋反应10h；
(6)产物3000r/min离心，纯水清洗3次，最后一次乙腈清洗，自然干燥。
实施方案2
(1)称取0.3g SBA-15与150ml无水乙醇混合，超声混匀；
(2)加入50ml的APTES，在60℃水浴搅拌5h；
(3)5000r/min离心5min后，依次用纯水和无水乙醇洗3次，0.22μm有机系滤膜抽滤；
(4)取抽滤后的合成产物40℃真空干燥，制得SBA-15@APTES；
(5)称取0.02gSBA-15@APTES、0.10gNHS、0.40gEDC、0.02gCHCA，加入1ml纯水混匀，避光条件下涡旋反应4h；
(6)产物5000r/min离心，纯水清洗3次，最后一次乙腈清洗，自然干燥。
Claims (2)
1.一种α-氰基-4-羟基肉桂酸(CHCA)与硅基介孔材料共价偶联基质的合成方法，其特征在于包括以下合成步骤：
(1)配制10～100mg/mL的介孔材料悬浊液，超声辅助分散，溶剂为无水乙醇；
(2)按照3-氨丙基三乙氧基硅烷(APTES)∶硅基介孔材料体积比0.5～3∶1的比例加入APTES，50～100℃水浴搅拌反应4～12小时；
(3)反应液2000r/min～10000r/min离心2～10min；依次用去离子水和无水乙醇洗涤3～5次；
(4)孔径为0.22μm以下的滤膜抽滤，滤膜截留的合成产物30～60℃真空干燥，制得硅基介孔材料@APTES；
(5)按照硅基介孔材料@APTES，CHCA，N-羟基丁二酰亚胺(NHS)，1-乙基-(3-二甲基氨基丙基)碳酰二亚胺盐酸盐(EDC·HCl)质量比1∶1∶3～5∶12～20的比例混合，加入纯水使CHCA最终浓度为10～50mg/mL，避光条件下反应4h以上；
(6)纯水离心洗涤3次后，用乙腈洗涤，自然干燥备用。
2.根据权利要求1所述的合成方法，如上所述的介孔硅材料为SBA-15或其它含有硅羟基的介孔材料。
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