顺序注射化学发光联用技术选择性测定三种氨基酸的研究
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摘要
生命科学是21世纪最重要的科学研究领域,氨基酸分析在生命科学研究中占有重要的地位。建立准确、灵敏、简便、快捷的氨基酸分析方法对蛋白质化学、临床医学、生理研究、及食品分析有着重要意义。
化学发光法以其灵敏度高、分析速度快、简便和线性范围宽等诸多优点,促使人们做了大量的研究工作。它在生命科学、临床医学和环境科学等许多领域的应用都已成为研究的热点。流动注射分析技术可以精确地控制试剂和试样的体积以及混合时间,提高方法的重现性；易于控制采样操作、减少试剂和试样的消耗；自动化程度高,显著提高分析频率。顺序注射分析作为流动分析的一个分支或第二代流动注射分析在上世纪九十年代被提出来。它更新了仪器装置,简化了操作使其更易微机化,达到了自动化和智能化的新水平,可以用同一装置完成不同组分的检测而无需改变流路的设置,成为流动注射分析研究中最活跃的领域之一。流动注射和顺序注射及其混合体系已发展成为自动分析和在线样品处理技术的主要手段。流动分析进样和化学发光检测技术耦合,保留了化学发光检测技术固有的优点,克服了通常化学发光分析中因反应速度快,反应过程难以控制,重现性较差的弊病,进一步改善了后者的分析性能,显著地提高了分析结果重现性、准确度和分析速度。本文将顺序注射进样技术和化学发光检测方法联用,建立了简便、快速、灵敏、选择性测定氨基酸含量的分析方法,并讨论了部分化学发光反应体系的反应机理。
第一章简要评述了近年来应用于氨基酸分析的主要方法,包括色谱分离方法、化学计量学解析,各类光学检测方法和其它分析方法等。
第二章将顺序注射进样技术与化学发光检测技术联用,详细研究了顺序注射条件下特有的进样顺序对发光信号强度的影响。模拟实验结果表明,对于快速发光反应体系,因待测试样区带排序位置不同引起的试样分散程度不一是发光强度变化的主要因素。基于丁二酮肟存在下组氨酸能够增强Mn(Ⅱ)盐对鲁米诺与过氧化氢发光反应的催化能力,建立了顺序注射化学发光联用技术选择性测定组氨酸含量的新方法,线性响应范围为5.0×10-7～1.0×10-3 mol/L,检出限(3σ)为2×10-7mol/L,方法的相对标准偏差(R.S.D.)为0.97%(4.0×10-5mol/L,n=11)。在实际样品分析中,回收率在90.0～103.3%之间。
第三章研究了Ce(Ⅳ)-Tween20-Trp发光体系。在酸性介质中,色氨酸能够显著增强Ce(Ⅳ)和Tween20的发光反应。据此,建立了顺序注射化学发光联用技术测定色氨酸的新方法。线性分析范围为2.0×10-7～8.0×10-6mol/L,检出限为1.5×10-7 mol/L,方法的相对标准偏差为0.7%。与Ce(Ⅳ)-Trp直接发光反应相比较,本方法线性分析范围下降了一个数量级。该方法用于氨基酸注射液和啤酒中色氨含量的测定,结果满意。此外,本章通过研究相关反应物和反应产物的化学发光光谱、吸收光谱和荧光光谱,探讨了Ce(IV)-Tween20-Trp体系可能的发光反应机理。该反应的发光体为Tween20的中间氧化产物,在这个化学发光反应中,色氨酸是Ce(Ⅳ)与Tween20反应的增敏剂。
第四章研究了色氨酸和酪氨酸对Ce(IV)-quinine-Cys发光体系的抑制效应；提出了利用Ce(IV)-quinine-Cys-(Trp+Tyr)反应体系中色氨酸和酪氨酸的抑制效应和Ce(IV)-Tween40-Trp体系中色氨酸的增强效应,同时测定色氨酸和酪氨酸含量的化学发新方法；采用双泵双阀的顺序注射进样和空气微柱间隔发光信号,消除了顺序注射流路毗邻信号间的干扰,成功实现了酪氨酸和色氨酸同时检测。通过色氨酸和酪氨酸对Ce(IV)-quinine-Cys体系的抑制作用,得出二者总的含量；利用色氨酸对Ce(IV)-Tween40体系的增敏作用,测得色氨酸的含量,总量与色氨酸含量之差就是酪氨酸的含量。对于Ce(IV)-quinine-Cys-(Trp+Tyr)反应体系,测定范围为3×10-7～1.2×10-5 mol/L时,检出限为2.9×10-6 mol/L,方法的相对标准偏差为1.1%(n=9)；对于Ce(IV)-Tween40-Trp发光体系,测定范围为2×10-7～1.4×10-5 mol/L,检出限为9.0×10-8 mol/L,连续9次测定色氨酸的相对标准偏差为1.3%。探讨了可能的反应机理,认为Ce(IV)-quinine-Cys-(Trp+Tyr)体系发光反应的发光体为奎宁；而Ce(IV)-Tween40-Trp体系发光反应的发光体可能为Tween40的中间氧化产物。用该方法实现了氨基酸注射液、啤酒、牛奶、豆浆和血清等样品中色氨酸和酪氨酸含量的测定,其中,牛奶和豆浆中色氨酸和酪氨酸测定结果与对照方法一致。该方法检测下限和检出限低,适于痕量色氨酸和酪氨酸的测定。
综上所述,本文建立了顺序注射与化学发光联用技术选择性测定几种氨基酸的分析方法,方法具有操作简单、试剂和样品的消耗量少、灵敏度高、分析速度快的特点。实现了食品和药品中相应氨基酸的含量测定,提高了顺序注射与化学发光联用技术检测氨基酸的应用能力。研究了相关反应可能的反应机理,为化学发光的机理研究提供了参考。
Life science is one of the most important research domains in this century, and amino acid analysis is one of the important analytical techniques in the investigation of life science. Therefore, it is necessary to develop accurate, sensitive, simple,and rapid methods for the analysis of amino acids.
Chemiluminescence (CL) method is an attractive and powerful detection technique due to its analytical advantages including low detection limit, very high sensitivity, wide linear dynamic range, and fast response, and it has been used in life science, clinical medicine, and environmental science.
Flow injection analysis (FIA) is well-established technique for rapid automated solution treatment and detection. Sequential injection analysis (SIA), as a branch of sampling means of FIA or second generation FIA, the principles upon which SI is based are similar to those of FIA, namely controlled partial dispersion and reproducible sample handing. In contrast to FIA, the flow programming in SIA allows the employment of complex chemistry without reconfiguration of the manifold, and the instrumentation is simpler and intrinsically robust, easy to automate and detect on-line with very low reagent consumption.
When chemiluminescence detection was combined with SIA analysis, its features were reserved, and the shortcomings, such as inconvenience of reaction process control and poor repeatability caused by fast reaction, were overcame. Combination CL with SIA remarkably improved the repeatability, accuracy and analytical frequency of the determination results.
In this paper, some new CL reaction systems were proposed and studied. Three new SIA-CL methods were developed for selective determination of amino acids. In addition, the possible reaction mechanisms of the CL reaction systems were discussed. The dissertation is divided into four chapters:
Chapter 1 briefly reviewed main methods for the determination of amino acids in recent years, and these methods include chromatography, chemometrics procedure, and photometric measurement method without chromatograph.
In Chapter 2 of the dissertation, a simulation experiment was proceeded to explain the reason in which various zone stacking sequences influence the CL intensity in sequential injection sampling. As a result, physical dispersion caused by sampling sequences for rapid CL reaction is the major factor that influenced luminescent intensity. In addition, a SIA-CL method for the determination of histidine was developed, based on the reaction that histidine increased the catalytic activity of manganese (Ⅱ) salts in luminol-hydrogen peroxide reaction system in the presence of dioximes in sodium borate medium. At optimized conditions, histidine can be determined in the linear range from 5.0×10-7 to 1.0×10-3 mol/L with a detection limit (3σ) of 2×10-7 mol/L for 60μL sample. The relative standard deviation (R.S.D.) for eleven repeated measurements of 4×10-5 mol/L histidine was 0.97%, and the sampling frequency was 80 h-1, and the recoveries were 90.0～103.3%. The proposed method has been successfully applied to the determination of histidine in some beer.
In Chapter 3 of the dissertation, it was observed that the chemiluminescence intensity from the reaction of acidic Ce(Ⅳ) and Tween20 was greatly enhanced by tryptophan. Based on Ce(Ⅳ)-Tween20-Trp reaction, a sequential injection procedure with chemiluminescence detection was proposed for the determination of tryptophan. The influences of several physical and chemical parameters were assessed.
Under the selected working conditions, a linear dynamic range of 2.0×10-7～8.0×10-6 mol/L, a 3σdetection limit of 1.5×10-7 mol/L and a coefficient of variation of 0.7% at 3.0×10-6 mol/L level were obtained. The procedure was applied to the determination of tryptophan in beer and amino acid injections, and the recoveries were 91.4～106.9%. At the same time, the possible reaction mechanism was studied, the emitter in the CL reaction is probably a transient intermediate product of Tween20 oxidized by Ce(IV), and tryptophan is an enhancer for the reaction of Ce(IV) and Tween20.
In Chapter 4 of the dissertation, two new chemiluminescence reaction systems, namely Ce(Ⅳ)-quinine-Cys-(Trp+Tyr) and Ce(Ⅳ)-Tween40-Trp were studied. The possible reaction mechanisms were also investigated. Furthermore, a SIA manifold with double-pump and double-multiposition valve was developed for simultaneous determination of tryptophan and tyrosine. The total amounts of tyrosine and tryptophan could be obtained by their quantificational inhibition to the CL reaction of Ce(Ⅳ)-quinine-Cys, and the accurate content of tryptophan was obtained from its quantificational enhancement to the CL reaction of Ce(Ⅳ)-Tween40, and the content of tyrosine was obtained by subtracted content of tryptophan from the total content of tyrosine and tryptophan.
To the CL reaction of Ce(Ⅳ)-quinine-Cys-(Trp+Tyr) and Ce(Ⅳ)-Tween40-Trp, the dynamic range of 3.0×10-7～1.2×10-5 mol/L and 2.0×10-7～1.4×10-5 mol/L, the detection limits (3σ) of 2.9×10-7 mol/L and 9.0×10-8 mol/L, and the relative standard deviation (R.S.D.) of 1.1% and 1.3% were obtained, respectively. The method was applied to determination of tyrosine and tryptophan in amino acid injection, beer, serum, soybean milk and milk.
A microwave-assistance treatment procedure was used to hydrolyze soybean milk and milk samples with 5.0 mol/L sodium hydroxide for 50 s, and the procedure dramatically improved the treatment efficiency.
In conclusion, this dissertation demonstrated selective determinations of amino acids by sequential injection with chemiluminescence detection. These proposed methods are sensitive, simple, and less reagents consumption and waste output, and the methods were applied to determination of three amino acid contents in food beverage, blood serum, and amino acid injection.
化学发光法以其灵敏度高、分析速度快、简便和线性范围宽等诸多优点,促使人们做了大量的研究工作。它在生命科学、临床医学和环境科学等许多领域的应用都已成为研究的热点。流动注射分析技术可以精确地控制试剂和试样的体积以及混合时间,提高方法的重现性；易于控制采样操作、减少试剂和试样的消耗；自动化程度高,显著提高分析频率。顺序注射分析作为流动分析的一个分支或第二代流动注射分析在上世纪九十年代被提出来。它更新了仪器装置,简化了操作使其更易微机化,达到了自动化和智能化的新水平,可以用同一装置完成不同组分的检测而无需改变流路的设置,成为流动注射分析研究中最活跃的领域之一。流动注射和顺序注射及其混合体系已发展成为自动分析和在线样品处理技术的主要手段。流动分析进样和化学发光检测技术耦合,保留了化学发光检测技术固有的优点,克服了通常化学发光分析中因反应速度快,反应过程难以控制,重现性较差的弊病,进一步改善了后者的分析性能,显著地提高了分析结果重现性、准确度和分析速度。本文将顺序注射进样技术和化学发光检测方法联用,建立了简便、快速、灵敏、选择性测定氨基酸含量的分析方法,并讨论了部分化学发光反应体系的反应机理。
第一章简要评述了近年来应用于氨基酸分析的主要方法,包括色谱分离方法、化学计量学解析,各类光学检测方法和其它分析方法等。
第二章将顺序注射进样技术与化学发光检测技术联用,详细研究了顺序注射条件下特有的进样顺序对发光信号强度的影响。模拟实验结果表明,对于快速发光反应体系,因待测试样区带排序位置不同引起的试样分散程度不一是发光强度变化的主要因素。基于丁二酮肟存在下组氨酸能够增强Mn(Ⅱ)盐对鲁米诺与过氧化氢发光反应的催化能力,建立了顺序注射化学发光联用技术选择性测定组氨酸含量的新方法,线性响应范围为5.0×10-7～1.0×10-3 mol/L,检出限(3σ)为2×10-7mol/L,方法的相对标准偏差(R.S.D.)为0.97%(4.0×10-5mol/L,n=11)。在实际样品分析中,回收率在90.0～103.3%之间。
第三章研究了Ce(Ⅳ)-Tween20-Trp发光体系。在酸性介质中,色氨酸能够显著增强Ce(Ⅳ)和Tween20的发光反应。据此,建立了顺序注射化学发光联用技术测定色氨酸的新方法。线性分析范围为2.0×10-7～8.0×10-6mol/L,检出限为1.5×10-7 mol/L,方法的相对标准偏差为0.7%。与Ce(Ⅳ)-Trp直接发光反应相比较,本方法线性分析范围下降了一个数量级。该方法用于氨基酸注射液和啤酒中色氨含量的测定,结果满意。此外,本章通过研究相关反应物和反应产物的化学发光光谱、吸收光谱和荧光光谱,探讨了Ce(IV)-Tween20-Trp体系可能的发光反应机理。该反应的发光体为Tween20的中间氧化产物,在这个化学发光反应中,色氨酸是Ce(Ⅳ)与Tween20反应的增敏剂。
第四章研究了色氨酸和酪氨酸对Ce(IV)-quinine-Cys发光体系的抑制效应；提出了利用Ce(IV)-quinine-Cys-(Trp+Tyr)反应体系中色氨酸和酪氨酸的抑制效应和Ce(IV)-Tween40-Trp体系中色氨酸的增强效应,同时测定色氨酸和酪氨酸含量的化学发新方法；采用双泵双阀的顺序注射进样和空气微柱间隔发光信号,消除了顺序注射流路毗邻信号间的干扰,成功实现了酪氨酸和色氨酸同时检测。通过色氨酸和酪氨酸对Ce(IV)-quinine-Cys体系的抑制作用,得出二者总的含量；利用色氨酸对Ce(IV)-Tween40体系的增敏作用,测得色氨酸的含量,总量与色氨酸含量之差就是酪氨酸的含量。对于Ce(IV)-quinine-Cys-(Trp+Tyr)反应体系,测定范围为3×10-7～1.2×10-5 mol/L时,检出限为2.9×10-6 mol/L,方法的相对标准偏差为1.1%(n=9)；对于Ce(IV)-Tween40-Trp发光体系,测定范围为2×10-7～1.4×10-5 mol/L,检出限为9.0×10-8 mol/L,连续9次测定色氨酸的相对标准偏差为1.3%。探讨了可能的反应机理,认为Ce(IV)-quinine-Cys-(Trp+Tyr)体系发光反应的发光体为奎宁；而Ce(IV)-Tween40-Trp体系发光反应的发光体可能为Tween40的中间氧化产物。用该方法实现了氨基酸注射液、啤酒、牛奶、豆浆和血清等样品中色氨酸和酪氨酸含量的测定,其中,牛奶和豆浆中色氨酸和酪氨酸测定结果与对照方法一致。该方法检测下限和检出限低,适于痕量色氨酸和酪氨酸的测定。
综上所述,本文建立了顺序注射与化学发光联用技术选择性测定几种氨基酸的分析方法,方法具有操作简单、试剂和样品的消耗量少、灵敏度高、分析速度快的特点。实现了食品和药品中相应氨基酸的含量测定,提高了顺序注射与化学发光联用技术检测氨基酸的应用能力。研究了相关反应可能的反应机理,为化学发光的机理研究提供了参考。
Life science is one of the most important research domains in this century, and amino acid analysis is one of the important analytical techniques in the investigation of life science. Therefore, it is necessary to develop accurate, sensitive, simple,and rapid methods for the analysis of amino acids.
Chemiluminescence (CL) method is an attractive and powerful detection technique due to its analytical advantages including low detection limit, very high sensitivity, wide linear dynamic range, and fast response, and it has been used in life science, clinical medicine, and environmental science.
Flow injection analysis (FIA) is well-established technique for rapid automated solution treatment and detection. Sequential injection analysis (SIA), as a branch of sampling means of FIA or second generation FIA, the principles upon which SI is based are similar to those of FIA, namely controlled partial dispersion and reproducible sample handing. In contrast to FIA, the flow programming in SIA allows the employment of complex chemistry without reconfiguration of the manifold, and the instrumentation is simpler and intrinsically robust, easy to automate and detect on-line with very low reagent consumption.
When chemiluminescence detection was combined with SIA analysis, its features were reserved, and the shortcomings, such as inconvenience of reaction process control and poor repeatability caused by fast reaction, were overcame. Combination CL with SIA remarkably improved the repeatability, accuracy and analytical frequency of the determination results.
In this paper, some new CL reaction systems were proposed and studied. Three new SIA-CL methods were developed for selective determination of amino acids. In addition, the possible reaction mechanisms of the CL reaction systems were discussed. The dissertation is divided into four chapters:
Chapter 1 briefly reviewed main methods for the determination of amino acids in recent years, and these methods include chromatography, chemometrics procedure, and photometric measurement method without chromatograph.
In Chapter 2 of the dissertation, a simulation experiment was proceeded to explain the reason in which various zone stacking sequences influence the CL intensity in sequential injection sampling. As a result, physical dispersion caused by sampling sequences for rapid CL reaction is the major factor that influenced luminescent intensity. In addition, a SIA-CL method for the determination of histidine was developed, based on the reaction that histidine increased the catalytic activity of manganese (Ⅱ) salts in luminol-hydrogen peroxide reaction system in the presence of dioximes in sodium borate medium. At optimized conditions, histidine can be determined in the linear range from 5.0×10-7 to 1.0×10-3 mol/L with a detection limit (3σ) of 2×10-7 mol/L for 60μL sample. The relative standard deviation (R.S.D.) for eleven repeated measurements of 4×10-5 mol/L histidine was 0.97%, and the sampling frequency was 80 h-1, and the recoveries were 90.0～103.3%. The proposed method has been successfully applied to the determination of histidine in some beer.
In Chapter 3 of the dissertation, it was observed that the chemiluminescence intensity from the reaction of acidic Ce(Ⅳ) and Tween20 was greatly enhanced by tryptophan. Based on Ce(Ⅳ)-Tween20-Trp reaction, a sequential injection procedure with chemiluminescence detection was proposed for the determination of tryptophan. The influences of several physical and chemical parameters were assessed.
Under the selected working conditions, a linear dynamic range of 2.0×10-7～8.0×10-6 mol/L, a 3σdetection limit of 1.5×10-7 mol/L and a coefficient of variation of 0.7% at 3.0×10-6 mol/L level were obtained. The procedure was applied to the determination of tryptophan in beer and amino acid injections, and the recoveries were 91.4～106.9%. At the same time, the possible reaction mechanism was studied, the emitter in the CL reaction is probably a transient intermediate product of Tween20 oxidized by Ce(IV), and tryptophan is an enhancer for the reaction of Ce(IV) and Tween20.
In Chapter 4 of the dissertation, two new chemiluminescence reaction systems, namely Ce(Ⅳ)-quinine-Cys-(Trp+Tyr) and Ce(Ⅳ)-Tween40-Trp were studied. The possible reaction mechanisms were also investigated. Furthermore, a SIA manifold with double-pump and double-multiposition valve was developed for simultaneous determination of tryptophan and tyrosine. The total amounts of tyrosine and tryptophan could be obtained by their quantificational inhibition to the CL reaction of Ce(Ⅳ)-quinine-Cys, and the accurate content of tryptophan was obtained from its quantificational enhancement to the CL reaction of Ce(Ⅳ)-Tween40, and the content of tyrosine was obtained by subtracted content of tryptophan from the total content of tyrosine and tryptophan.
To the CL reaction of Ce(Ⅳ)-quinine-Cys-(Trp+Tyr) and Ce(Ⅳ)-Tween40-Trp, the dynamic range of 3.0×10-7～1.2×10-5 mol/L and 2.0×10-7～1.4×10-5 mol/L, the detection limits (3σ) of 2.9×10-7 mol/L and 9.0×10-8 mol/L, and the relative standard deviation (R.S.D.) of 1.1% and 1.3% were obtained, respectively. The method was applied to determination of tyrosine and tryptophan in amino acid injection, beer, serum, soybean milk and milk.
A microwave-assistance treatment procedure was used to hydrolyze soybean milk and milk samples with 5.0 mol/L sodium hydroxide for 50 s, and the procedure dramatically improved the treatment efficiency.
In conclusion, this dissertation demonstrated selective determinations of amino acids by sequential injection with chemiluminescence detection. These proposed methods are sensitive, simple, and less reagents consumption and waste output, and the methods were applied to determination of three amino acid contents in food beverage, blood serum, and amino acid injection.
引文
1.邹忠梅,喻长远.人体生命之源-氨基酸[M],北京：中国医药科技出版社,2000.2,16-25.
2.徐国财,张晓梅.有机化学[M],北京：科学出版社,2008.6,409-410.
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4. Spackman D H, Stein W H, Moore S. Automatic recording apparatus for use in chromatography of amino acids [J], Anal. Chem.,1958,30(7):1190-1206.
5.中华人民共和国国家标准食物中氨基酸的测定方法(GB/T 14965—1994).
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