基于联二萘酚衍生物模拟酶受体的合成与应用
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摘要
超分子化学是研究两种以上的化学物质（分子、离子等）通过分子间力相结合而形成的复杂有序且具有特定功能的超分子体系的科学。利用人工受体建立化学仿生体系或化学模型来研究生物体内的分子识别现象已成为超分子化学和生物有机化学前沿富于挑战性的课题之一。近些年来发现，一些具有特定结构的光学活性联二萘酚衍生物作为磷酸吡哆醛的人工模拟酶分子，在手性氨基酸构型转换、手性氨基醇对映选择性识别以及萃取拆分等方面具有很好地应用前景。此外，具有光学活性的1,1'-联二萘酚及其衍生物由于其本身具有C2对称轴而具有独特的化学性质和手性诱导功能，且在适合结构基团修饰下能产生很强的荧光，在离子荧光识别等方面得到了广泛的应用。荧光化学传感器具有选择性好、简便快速、灵敏度高等优点，被广泛地用于检测各种金属离子和阴离子。本论文设计合成了两类不同的受体：第一类是1,1'-联-2-萘酚类人工模拟酶分子,并研究了其对L-氨基酸的构型转化和手性氨基醇的对映选择性识别；第二类是设计合成基于联二萘酚衍生物的化学传感器，并研究了其识别和传感性质，取得了一些有意义的结果。具体内容如下：
1、简要介绍了该类化合物的合成方法，综述了近年来联二萘酚类磷酸吡哆醛模拟酶在手性氨基酸构型转换、手性氨基醇对映选择性识别以及萃取拆分等方面的应用。在离子识别方面，对近几年报道的识别阳离子、阴离子的基于联二萘酚衍生物的化学传感器进行了综述。
2、在联二萘酚的基础上设计、合成了两种新的含有胍基或环己基脲结构的联二萘酚类模拟酶分子2-1和2-2。其次，本文采用官能团保护法，探索了模拟酶分子2-3的合成，并表征了它们的结构。
3、模拟酶分子2-1和2-2既可以用作构型转换试剂用于L-α-氨基酸的构型转换，而且对手性氨基醇具有对映选择性识别作用。在氘代二甲基亚砜溶液中，有三乙胺存在下，利用核磁共振氢谱跟踪，分别考察了它们对L-α-氨基酸的构型转换作用。同时，在氘代氯仿中，利用核磁共振氢谱跟踪，分别研究了它们对手性氨基醇的对映选择性识别作用。结果表明，2-1和2-2都可与氨基酸形成希夫碱，然后通过差相异构化作用，将L-α-氨基酸转变为D-α-氨基酸，其中2-1对丝氨酸的构型转换效率(KD/KL)为3.5，2-2对组氨酸的构型转换效率(KD/KL)为5.2，同时2-1对手性2-氨基-1-丙醇的立体选择性比率(KR/KS)为6.25，2-2对手性2-氨基-1-丁醇的立体选择性比率(KR/KS)为1.97。此外，还将本研究结果与部分已知模拟酶的作用进行了对比，并简单讨论了差异性。
4、在联二萘酚的骨架上引入4-氨基-苯并15-冠-5基团，合成了一种新的荧光传感器4-3。当在乙腈与HEPES缓冲溶液为(v/v=1:1)的溶液中加入10倍于4-3的铜离子溶液后，化合物4-3的荧光发射峰几乎被完全淬灭；而相同倍数的其它金属离子(Hg~(2+), Pb~(2+),Sr~(2+), Ba~(2+), Cd~(2+), Ni~(2+), Co~(2+), Fe~(2+), Mn~(2+), Zn~(2+), Al3+, Mg~(2+), K+, Fe3+, Cr3+, Na+)的加入只使4-3荧光强度稍微降低。根据滴定实验数据，采用基于12的Benesi-Hildebrand方程线性拟合，结果表明4-3与Cu~(2+)之间是以12的结合比相结合的；通过抗干扰实验发现，4-3对Cu~(2+)的这种选择性的荧光识别作用受其它金属离子(Hg~(2+), Pb~(2+), Sr~(2+), Ba~(2+), Cd~(2+), Ni~(2+),Co~(2+), Fe~(2+), Mn~(2+), Zn~(2+), Al3+, Mg~(2+), K+, Fe3+, Cr3+, Na+)的干扰比较小。
5、在联二萘酚的骨架上引入2-氨基苯并咪唑基团，合成了一种新型的荧光传感器5-1。在无水乙腈中当所加F-浓度为受体5-1的40倍的时，受体5-1的荧光强度基本达到平衡不再增强，而相同倍数的其它阴离子(H_2PO_4~-, Cl~-, Br~-, I~-, HSO_4~-, NO_3~-, Ac~-)的加入只使5-1的荧光强度略微增强。采用等摩尔连续法(Job’s plot)对F-与受体5-1的结合比进行了验证，结果表明受体5-1与F-是以12的方式结合的；通过抗干扰实验验证，在此识别过程其它阴离子(H2PO4-, Cl-, Br-, I-, HSO4-, NO3-, Ac-)对其有一定的干扰。
Supramolecular chemistry is a science of study on the intermolecular interactionsbetween two or more chemical species which could form a complicated and orderedsupramolecular system with certain functions. Study on molecular recognition using artificialreceptors to construct the chemical models or biomimetic system is one of the challenges inthe frontiers of bioorganic chemistry and supramolecular chemistry. Some recently studiedenzyme mimic binaphthol derivatives have the function of amino acid chiral conversion, theyalso can be used for enantioselective recognition of chiral1,2-amino alcohols and extractiveseparation of amino acids as well as1,2-amino alcohols are reviewed. Moreover, opticallyactive BINOL and its derivatives have unique chemical properties and chiral inductivefunction because of the C2symmetric axis. When they are introduced into a suitablefunctional group, they can produce strong fluorescence, so they are widely applied toasymmetric catalytic reactions and fluorescence recognition of chiral object. Fluorescencechemosensors are widely used to detect metal ions and anions because of their high selectivity,sensitivity and simplicity. In this thesis, two kinds of different receptors based on binolderivatives were synthesized and investigated for their applications. Firstly, enzyme mimicbinapthol derivatives were synthesized and investigated for their applications in L-aminoacids chiral conversion and1,2-amino alcohols enantioselective recognition. Secondly, twonew chemosensors based on binol derivatives were synthesized and investigated for theirapplications in the detection of copper ion (Cu2+) and fluorin ion (F-). The details are asfollows:
1. The methods of synthesizing receptor were introduced briefly. The application of PLPenzyme mimic binaphthol derivatives in chiral conversion of amino acids andenantioselective recognition of chiral1,2-amino alcohols in recent years were summarized. Inthe ion recognition, binaphthol based chemosensors for anion and cation recognizing in recentyears were summarized.
2. Two binaphthol based enzyme mimic reagents2-1and2-2, which containingcyclohexyl urea and guanidinium hydrogen bonding moiety respectively, were synthesizedand characterized.
3. Both molecules not only can be applied to amino acid chirality inversion but also canbe applied to enantioselective recognition of1,2-amino alcohols. The chirality inversioneffects of2-1and2-2for L-α-amino acids to D-α-amino acids were examined by1H NMR inDMSO-d6in the presence of triethylamine. The results showed that2-1and2-2can react withthe tested L-α-amino acids to form corresponding imine and subsequently convert partiallythe amino acid from its L form to D form through an epimerization processes. The chiralityinversion efficiency (KD/KL) of2-2to L-histidine is5.2, the value of (KD/KL) of2-1toL-serine is3.5. The enantioselective recognition effects of2-1and2-2for1,2-amino alcoholwere examined by1H NMR in CDCl3. The enantioselective recognition efficiency(KR/KS)of2-1to2-amino-1-ppropanol is6.25, the value of (KR/KS) of2-2to2-amino-1-butanol is1.97.Comparision of the application of2-1and2-2with those of some known enzyme mimicreagents are also discussed.
4. A new metal ion fluorescence sensor4-3was designed and synthesized by introducing4-amino benzo-15-crown-5into the framework of Binol which showed a high selectivitytowards Cu~(2+)through fluorescence quenching in CH3CN:HEPES (v:v=1:1). The bindingstoichiometry of4-3and Cu~(2+)is12according to the titration data based onBenesi-Hildebrand plot. The Cu~(2+)recognition process of4-3is not significantly influenced byother coexisting metal ions (Hg~(2+), Pb~(2+), Sr~(2+), Ba~(2+), Cd~(2+), Ni~(2+), Co~(2+), Fe~(2+), Mn~(2+), Zn~(2+), Al3+,Mg~(2+), K+, Fe3+, Cr3+, Na+).
5. A new anion fluorescence sensor5-1was designed and synthesized by combiningBinol and2-benzimidazolamine which showed a high selectivity towards F-throughfluorescence enhancement in CH3CN. The results of Job's plot based on a1:2binding modeindicated that sensor5-1and F-formed a1:2stoichiometric complex. This highly selective F-recognition process of5-1is barely influenced by other coexisting anions (F~-, Cl~-, Br~-, I~-,HSO_4~-, NO_3~-, Ac~-).
1、简要介绍了该类化合物的合成方法，综述了近年来联二萘酚类磷酸吡哆醛模拟酶在手性氨基酸构型转换、手性氨基醇对映选择性识别以及萃取拆分等方面的应用。在离子识别方面，对近几年报道的识别阳离子、阴离子的基于联二萘酚衍生物的化学传感器进行了综述。
2、在联二萘酚的基础上设计、合成了两种新的含有胍基或环己基脲结构的联二萘酚类模拟酶分子2-1和2-2。其次，本文采用官能团保护法，探索了模拟酶分子2-3的合成，并表征了它们的结构。
3、模拟酶分子2-1和2-2既可以用作构型转换试剂用于L-α-氨基酸的构型转换，而且对手性氨基醇具有对映选择性识别作用。在氘代二甲基亚砜溶液中，有三乙胺存在下，利用核磁共振氢谱跟踪，分别考察了它们对L-α-氨基酸的构型转换作用。同时，在氘代氯仿中，利用核磁共振氢谱跟踪，分别研究了它们对手性氨基醇的对映选择性识别作用。结果表明，2-1和2-2都可与氨基酸形成希夫碱，然后通过差相异构化作用，将L-α-氨基酸转变为D-α-氨基酸，其中2-1对丝氨酸的构型转换效率(KD/KL)为3.5，2-2对组氨酸的构型转换效率(KD/KL)为5.2，同时2-1对手性2-氨基-1-丙醇的立体选择性比率(KR/KS)为6.25，2-2对手性2-氨基-1-丁醇的立体选择性比率(KR/KS)为1.97。此外，还将本研究结果与部分已知模拟酶的作用进行了对比，并简单讨论了差异性。
4、在联二萘酚的骨架上引入4-氨基-苯并15-冠-5基团，合成了一种新的荧光传感器4-3。当在乙腈与HEPES缓冲溶液为(v/v=1:1)的溶液中加入10倍于4-3的铜离子溶液后，化合物4-3的荧光发射峰几乎被完全淬灭；而相同倍数的其它金属离子(Hg~(2+), Pb~(2+),Sr~(2+), Ba~(2+), Cd~(2+), Ni~(2+), Co~(2+), Fe~(2+), Mn~(2+), Zn~(2+), Al3+, Mg~(2+), K+, Fe3+, Cr3+, Na+)的加入只使4-3荧光强度稍微降低。根据滴定实验数据，采用基于12的Benesi-Hildebrand方程线性拟合，结果表明4-3与Cu~(2+)之间是以12的结合比相结合的；通过抗干扰实验发现，4-3对Cu~(2+)的这种选择性的荧光识别作用受其它金属离子(Hg~(2+), Pb~(2+), Sr~(2+), Ba~(2+), Cd~(2+), Ni~(2+),Co~(2+), Fe~(2+), Mn~(2+), Zn~(2+), Al3+, Mg~(2+), K+, Fe3+, Cr3+, Na+)的干扰比较小。
5、在联二萘酚的骨架上引入2-氨基苯并咪唑基团，合成了一种新型的荧光传感器5-1。在无水乙腈中当所加F-浓度为受体5-1的40倍的时，受体5-1的荧光强度基本达到平衡不再增强，而相同倍数的其它阴离子(H_2PO_4~-, Cl~-, Br~-, I~-, HSO_4~-, NO_3~-, Ac~-)的加入只使5-1的荧光强度略微增强。采用等摩尔连续法(Job’s plot)对F-与受体5-1的结合比进行了验证，结果表明受体5-1与F-是以12的方式结合的；通过抗干扰实验验证，在此识别过程其它阴离子(H2PO4-, Cl-, Br-, I-, HSO4-, NO3-, Ac-)对其有一定的干扰。
Supramolecular chemistry is a science of study on the intermolecular interactionsbetween two or more chemical species which could form a complicated and orderedsupramolecular system with certain functions. Study on molecular recognition using artificialreceptors to construct the chemical models or biomimetic system is one of the challenges inthe frontiers of bioorganic chemistry and supramolecular chemistry. Some recently studiedenzyme mimic binaphthol derivatives have the function of amino acid chiral conversion, theyalso can be used for enantioselective recognition of chiral1,2-amino alcohols and extractiveseparation of amino acids as well as1,2-amino alcohols are reviewed. Moreover, opticallyactive BINOL and its derivatives have unique chemical properties and chiral inductivefunction because of the C2symmetric axis. When they are introduced into a suitablefunctional group, they can produce strong fluorescence, so they are widely applied toasymmetric catalytic reactions and fluorescence recognition of chiral object. Fluorescencechemosensors are widely used to detect metal ions and anions because of their high selectivity,sensitivity and simplicity. In this thesis, two kinds of different receptors based on binolderivatives were synthesized and investigated for their applications. Firstly, enzyme mimicbinapthol derivatives were synthesized and investigated for their applications in L-aminoacids chiral conversion and1,2-amino alcohols enantioselective recognition. Secondly, twonew chemosensors based on binol derivatives were synthesized and investigated for theirapplications in the detection of copper ion (Cu2+) and fluorin ion (F-). The details are asfollows:
1. The methods of synthesizing receptor were introduced briefly. The application of PLPenzyme mimic binaphthol derivatives in chiral conversion of amino acids andenantioselective recognition of chiral1,2-amino alcohols in recent years were summarized. Inthe ion recognition, binaphthol based chemosensors for anion and cation recognizing in recentyears were summarized.
2. Two binaphthol based enzyme mimic reagents2-1and2-2, which containingcyclohexyl urea and guanidinium hydrogen bonding moiety respectively, were synthesizedand characterized.
3. Both molecules not only can be applied to amino acid chirality inversion but also canbe applied to enantioselective recognition of1,2-amino alcohols. The chirality inversioneffects of2-1and2-2for L-α-amino acids to D-α-amino acids were examined by1H NMR inDMSO-d6in the presence of triethylamine. The results showed that2-1and2-2can react withthe tested L-α-amino acids to form corresponding imine and subsequently convert partiallythe amino acid from its L form to D form through an epimerization processes. The chiralityinversion efficiency (KD/KL) of2-2to L-histidine is5.2, the value of (KD/KL) of2-1toL-serine is3.5. The enantioselective recognition effects of2-1and2-2for1,2-amino alcoholwere examined by1H NMR in CDCl3. The enantioselective recognition efficiency(KR/KS)of2-1to2-amino-1-ppropanol is6.25, the value of (KR/KS) of2-2to2-amino-1-butanol is1.97.Comparision of the application of2-1and2-2with those of some known enzyme mimicreagents are also discussed.
4. A new metal ion fluorescence sensor4-3was designed and synthesized by introducing4-amino benzo-15-crown-5into the framework of Binol which showed a high selectivitytowards Cu~(2+)through fluorescence quenching in CH3CN:HEPES (v:v=1:1). The bindingstoichiometry of4-3and Cu~(2+)is12according to the titration data based onBenesi-Hildebrand plot. The Cu~(2+)recognition process of4-3is not significantly influenced byother coexisting metal ions (Hg~(2+), Pb~(2+), Sr~(2+), Ba~(2+), Cd~(2+), Ni~(2+), Co~(2+), Fe~(2+), Mn~(2+), Zn~(2+), Al3+,Mg~(2+), K+, Fe3+, Cr3+, Na+).
5. A new anion fluorescence sensor5-1was designed and synthesized by combiningBinol and2-benzimidazolamine which showed a high selectivity towards F-throughfluorescence enhancement in CH3CN. The results of Job's plot based on a1:2binding modeindicated that sensor5-1and F-formed a1:2stoichiometric complex. This highly selective F-recognition process of5-1is barely influenced by other coexisting anions (F~-, Cl~-, Br~-, I~-,HSO_4~-, NO_3~-, Ac~-).
引文
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