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261.
Li W  Zhong Y  Lin B  Su Z 《Journal of chromatography. A》2001,905(1-2):299-307
A new program to characterize polyethylene glycol-modified (PEGylated) proteins is outlined using capillary zone electrophoresis (CZE). PEGylated ribonuclease A and lysozyme were selected as examples. Five separation procedures were compared to select out the mixed buffer of acetonitrile-water (1:1, v/v) at pH 2.5 as the best to characterize the PEGylated proteins without sample pretreatment. Polyethylene oxide (PEO) with a high molecular mass of 8 x 10(6) was applied to rinse the capillary to form a dynamic coating which would decrease the undesirable proteins adsorbed to the inner wall of the silica. The electroosmotic flow (EOF) mobility of the five procedures was determined, respectively. It is found that acetonitrile is mainly responsible for the good resolution of PEGylated proteins with the help of PEO coating in the semi-aqueous system. The low EOF mobility and current in the semi-aqueous system might also have some responsibility for the high resolution. The semi-aqueous procedure described in this paper also demonstrates higher resolution of natural proteins than aqueous ones.  相似文献   
262.
In this study, we investigated redox thermodynamics of myoglobin as well as the ionic (phosphate ions) and ligation (imidazole) effects via a dynamic electrochemical approach. We employed a previously established system that features nonmediated, direct electrochemistry of myoglobin and myoglobin in an immobilized state (i.e., diffusionless electrochemistry). Thermodynamics parameters were obtained by measuring redox potential (E degrees ') of myoglobin at varied temperature (T), in the presence and in the absence of specific ions or axial ligands. As a step further, we evaluated contributions from allosteric effect and axial iron ligation by partitioning E degrees ' changes into entropic and enthalpic terms. Compensation phenomena between the entropic and enthalpic changes were observed in all these cases. On the basis of these studies, we also correlated these phenomena to possible structural variations.  相似文献   
263.
为探讨急性心肌梗死(AMI)患者血清中K+、Na+、Ca2+、Fe2+、Mg2+含量变化,并研究其与心肌梗死患者之间的关系。选取2022年5月至2023年2月收治的AMI患者37例,同时选取健康体检者35例作为对照组。依据入院时或体检时收集的抽血样本进行临床生化分析,比较两组间血清K+、Na+、Ca2+、Fe2+、Mg2+含量,采用判别方程、主成分分析法(PCA),判断分析哪种金属离子对于心肌梗死的诊断价值大。结果表明,AMI患者的血清中Ca2+和Fe2+含量低于健康对照组,差异具有统计学意义。基于血钙、铁水平两组具有显著性差异,以它们为基础进行判别分析,获得判别函数式。将血清中K+、Na+、Ca2+、Fe2+、Mg2+  相似文献   
264.
稀土杂质元素直接影响高纯单金属稀土材料的整体性能,是高科技领域许多材料的重要组成部分。通过考察最佳的消解酸量、温度、时间、氧气反应气流量、稀释气流量,建立了基于三重四极杆电感耦合等离子体质谱仪(ICP-MS/MS)直接测定氧化铕中13种稀土杂质元素分析方法。该方法采用0.1%基体直接进样,可以很大程度提高前处理分析效率。利用碰撞模式测定氧化铕稀土中的Y、La、Pr、Nd、Sm、Gd、Tb、Dy、Ho、Er、Yb、Lu元素,氧气质量转移模式测定氧化铕中的Tm,两种模式结合可以有效去除多原子干扰,实现氧化铕的稳定测试分析。通过对氧化铕标准物质(GBW02902)直接测定分析,结果表明,在碰撞和氧气质量转移模式下,各元素线性相关系数(r)均大于 0.9999,方法检出限为0.001~0.023 mg/kg,测试精密度优于1.99%,13种元素的测试值都在认定值的不确定度范围之内。该分析方法操作简单,测试稳定,效率高,为实验室进行氧化铕材料中REE杂质的准确测试分析提供思路和借鉴。  相似文献   
265.
历史文物建筑修复与保护的首要步骤是对建材构件进行成分解析。但成型的混凝土构件成分复杂,传统技术难以直接分析。微区X射线荧光光谱具有速度快、无需前处理、可获得大面积高分辨的元素成像等优势,可用于此类混合物的原位分析。本文采用束斑为20μm的微区X射线荧光光谱仪,扫描成型混凝土构件以获得混合成分的元素分布图,结合基本参数定量法,对上海地区典型历史建筑混泥土构件进行元素定量。分析结果有效地解析了混凝土构建中骨料和凝胶材料的成分和含量,鉴别了涂层成分,解析了拌混工艺,鉴别了局部污染元素和致劣元素并分析致劣原因,为历史建筑修复材料选配、拌混工艺选择、除污及保护性预防劣化提供了科学的数据支撑。  相似文献   
266.
目的:建立不同产地半夏无机元素的分析方法和溯源体系,为半夏药材的质量控制和道地性评价提供技术支持。方法:采用电感耦合等离子体质谱法(ICP-MS)和电感耦合等离子体原子发射光谱法(ICP-AES)对我国6个主产区72份半夏样品中K、Ca、Na、Mg、Al等37种无机元素的含量进行测定,并采用方差分析、主成分分析、因子分析等计量学方法进行统计与评价。通过对比BP-神经网络算法、K-最近邻算法、最小二乘支持向量机等多种模式识别方法,探索适合半夏产地溯源的最佳模型。结果:不同产地半夏中无机元素的构成各具特征,各无机元素含量在产地间差异显著(P<0.05),其中La、Pb、As、Na、Bi、Hg、Sn、Cd、Ag 9种元素在不同产区间的差异最为明显;3D-plots图显示不同产地半夏样品分布相对集中,具备产地分类的可行性;KNN分类模型(曼哈顿距离)是半夏产地溯源的最佳方法,测试集的正确率达到100%。结论:无机元素分析技术结合适当的计量学模型可以实现半夏的产地溯源。  相似文献   
267.
锗在国防工业、航空航天和通信等领域中的战略性,锗含量的测定对于保证材料质量和满足国际标准至关重要。本文综述了锗含量测定方法的多种技术,包括分光光度法、原子荧光光谱法、原子吸收光谱法、电感耦合等离子体原子发射光谱法、电感耦合等离子体质谱法以及滴定法。在每个检测方法的介绍中,详细探讨了方法的原理、前处理步骤以及应用范围,并分别总结了各个方法的优势和不足。最后,强调了锗含量测定方法的意义,特别是在满足出口监管和促进科学研究方面的作用。同时对锗元素的测定方法进行了展望,为未来的发展提供了参考方向。  相似文献   
268.
The transient directing group (TDG) strategy allowed long awaited access to the direct β-C(sp3)–H functionalization of unmasked aliphatic aldehydes via palladium catalysis. However, the current techniques are restricted to terminal methyl functionalization, limiting their structural scopes and applicability. Herein, we report the development of a direct Pd-catalyzed methylene β-C–H arylation of linear unmasked aldehydes by using 3-amino-3-methylbutanoic acid as a TDG and 2-pyridone as an external ligand. Density functional theory calculations provided insights into the reaction mechanism and shed light on the roles of the external and transient directing ligands in the catalytic transformation.

Aliphatic aldehydes are among the most common structural units in organic and medicinal chemistry research. Direct C–H functionalization has enabled efficient and site-selective derivatization of aliphatic aldehydes.

Simple aliphatic functional groups enrich the skeletal backbones of many natural products, pharmaceuticals, and other industrial materials, influencing the utility and applications of these substances and dictating their reactivity and synthetic modification pathways. Aliphatic aldehydes are some of the most ubiquitous structural units in organic materials.1 Their relevance in nature and industry alike, combined with their reactivity and synthetic versatility, attracted much attention from the synthetic organic and medicinal chemistry communities over the years (Fig. 1).2 Efficient means to the functionalization of these molecules have always been highly sought after.Open in a separate windowFig. 1Select aliphatic aldehyde-containing medicines and biologically active molecules.Traditionally, scientists have utilized the high reactivity of the aldehyde moiety in derivatizing a variety of functional groups by the means of red-ox and nucleophilic addition reactions. The resourceful moiety was also notoriously used to install functional groups at the α-position via condensation and substitution pathways.3 Although β-functionalization is just as robust, it has generally been more restrictive as it often requires the use of α,β-unsaturated aldehydes.4,5 Hence, transition metal catalysis emerged as a powerful tool to access β-functionalization in saturated aldehydes.6 Most original examples of metal-catalyzed β-C–H functionalization of aliphatic aldehydes required the masking of aldehydes into better metal coordinating units since free unmasked aldehydes could not form stable intermediates with metals like palladium on their own.7 Although the masking of the aldehyde moiety into an oxime, for example, enabled the formation of stable 5-membered palladacycles, affording β-functionalized products, this system requires the installation of the directing group prior to the functionalization, as well as the subsequent unmasking upon the reaction completion, compromising the step economy and atom efficiency of the overall process.8 Besides, some masking and unmasking protocols might not be compatible with select substrates, especially ones rich in functional groups. As a result, the development of a one-step direct approach to the β-C–H functionalization of free aliphatic aldehydes was a demanding target for synthetic chemists.α-Amino acids have been demonstrated as effective transient directing groups (TDGs) in the remote functionalization of o-alkyl benzaldehydes and aliphatic ketones by the Yu group in 2016.9 Shortly after, our group disclosed the first report on the direct β-C–H arylation of aliphatic aldehydes using 3-aminopropanoic acid or 3-amino-3-methylbutanoic acid as a TDG.10 The TDG was found to play a similar role to that of the oxime directing group by binding to the substrate via reversible imine formation, upon which, it assists in the assembly of a stable palladacycle, effectively functionalizing the β-position.11 Since the binding of the TDG is reversible and temporary, it is automatically removed upon functionalization, yielding an efficient and step-economic transformation. This work was succeeded by many other reports that expanded the reaction and the TDG scopes.12–14 However, this system suffers from a significant restriction that demanded resolution; only substitution of methyl C–H bonds of linear aldehydes was made possible via this approach (Scheme 1a–e). The steric limitations caused by incorporating additional groups at the β-carbon proved to compromise the formation of the palladacycle intermediate, rendering the subsequent functionalization a difficult task.12Open in a separate windowScheme 1Pd-catalyzed β-C–H bond functionalization of aliphatic aldehydes enabled by transient directing groups.Encouraged by the recent surge in use of 2-pyridone ligands to stabilize palladacycle intermediates,15,16 we have successfully developed the first example of TDG-enabled Pd-catalyzed methylene β-C–H arylation in primary aldehydes via the assistance of 2-pyridones as external ligands (Scheme 1f). The incorporation of 2-pyridones proved to lower the activation energy of the C–H bond cleavage, promoting the formation of the intermediate palladacycles even in the presence of relatively bulky β-substituents.17 This key advancement significantly broadens the structural scopes and applications of this process and promises future asymmetric possibilities, perhaps via the use of a chiral TDG or external ligand or both. Notably, a closely related work from Yu''s group was published at almost the same time.18We commenced our investigation of the reaction parameters by employing n-pentanal (1a) as an unbiased linear aldehyde and 4-iodoanisole (2a) in the presence of catalytic Pd(OAc)2 and stoichiometric AgTFA, alongside 3-amino-3-methylbutanoic acid (TDG1) and 3-(trifluoromethyl)-5-nitropyridin-2-ol (L1) at 100 °C (ii) sources proved Pd(OAc)2 to be the optimal catalyst, while Pd(TFA)2, PdCl2 and PdBr2 provided only moderate yields (entries 10–12). Notably, a significantly lower yield was observed in the absence of the 2-pyridone ligand, and no desired product was isolated altogether in the absence of the TDG (entries 13 and 14). The incorporation of 15 mol% Pd catalyst was deemed necessary after only 55% yield of 3a was obtained when 10 mol% loading of Pd(OAc)2 was instead used (entry 15).Optimization of reaction conditionsa
EntryPd sourceL (mol%)TDG1 (mol%)Solvent (v/v, mL)Yield (%)
1Pd(OAc)2L1 (30)TDG1 (40)HFIP30
2Pd(OAc)2L1 (30)TDG1 (40)AcOH<5
3Pd(OAc)2L1 (30)TDG1 (40)HFIP/AcOH (1 : 1)28
4Pd(OAc)2L1 (30)TDG1 (40)HFIP/AcOH (9 : 1)47
5Pd(OAc)2L1 (30)TDG1 (40)HFIP/AcOH (1 : 9)<5
6Pd(OAc)2L1 (30)TDG1 (60)HFIP/AcOH (9 : 1)50
7Pd(OAc)2L1 (30)TDG1 (80)HFIP/AcOH (9 : 1)25
8Pd(OAc)2L1 (60)TDG1 (60)HFIP/AcOH (9 : 1)70(68)b
9Pd(OAc)2L1 (75)TDG1 (60)HFIP/AcOH (9 : 1)51
10Pd(TFA)2L1 (60)TDG1 (60)HFIP/AcOH (9 : 1)60
11PdCl2L1 (60)TDG1 (60)HFIP/AcOH (9 : 1)52
12PdBr2L1 (60)TDG1 (60)HFIP/AcOH (9 : 1)54
13Pd(OAc)2TDG1 (60)HFIP/AcOH (9 : 1)9
14Pd(OAc)2L1 (60)HFIP/AcOH (9 : 1)0
15cPd(OAc)2L1 (60)TDG1 (60)HFIP/AcOH (9 : 1)55
Open in a separate windowaReaction conditions: 1a (0.2 mmol), 2a (0.4 mmol), Pd source (15 mol%), AgTFA (0.3 mmol), L1, TDG1, solvent (2.0 mL), 100 °C, 12 h. Yields are based on 1a, determined by 1H-NMR using dibromomethane as an internal standard.bIsolated yield.cPd(OAc)2 (10 mol%).To advance our optimization of the reaction conditions, a variety of 2-pyridones and TDGs were tested (Scheme 2). Originally, pyridine-2(1H)-one (L2) was examined as the external ligand, but it only yielded the product (3a) in 7% NMR yield. Similarly, other mono- and di-substituted 2-pyridone ligands (L3–L10) also produced low yields, fixating L1 as the optimal external ligand. Next, various α- and β-amino acids (TDG1–10) were evaluated, yet TDG1 persisted as the optimal transient directing group. These amino acid screening results also suggest that a [5,6]-bicyclic palladium species is likely the key intermediate in this protocol since only β-amino acids were found to provide appreciable yields, whereas α-amino acids failed to yield more than trace amounts of the product. The supremacy of TDG1 when compared to other β-amino acids is presumably due to the Thorpe–Ingold effect that perhaps helps facilitate the C–H bond cleavage and stabilize the [5,6]-bicyclic intermediate further.Open in a separate windowScheme 2Optimization of 2-pyridone ligands and transient directing groups.With the optimized reaction conditions in hand, substrate scope study of primary aliphatic aldehydes was subsequently carried out (Scheme 3). A variety of linear primary aliphatic aldehydes bearing different chain lengths provided the corresponding products 3a–e in good yields. Notably, relatively sterically hindered methylene C–H bonds were also functionalized effectively (3f and 3g). Additionally, 4-phenylbutanal gave rise to the desired product 3h in a highly site-selective manner, suggesting that functionalization of the methylene β-C–H bond is predominantly favored over the more labile benzylic C–H bond. It is noteworthy that the amide group was also well-tolerated and the desired product 3j was isolated in 60% yield. As expected, with n-propanal as the substrate, β-mono- (3k1) and β,β-disubstituted products (3k2) were isolated in 22% and 21% yields respectively. However, in the absence of the key external 2-pyridone ligand, β-monosubstituted product (3k1) was obtained exclusively, albeit with a low yield, indicating preference for functionalizing the β-C(sp3)–H bond of the methyl group over the benzylic methylene group.Open in a separate windowScheme 3Scope of primary aliphatic aldehydes. Reaction conditions: 1 (0.2 mmol), 2a (0.4 mmol), Pd(OAc)2 (15 mol%), AgTFA (0.3 mmol), L1 (60 mol%), TDG1 (60 mol%), HFIP (1.8 mL), HOAc (0.2 mL), 100 °C, 12 h. Isolated yields. aL1 (60 mol%) was absent and yields are given in parentheses.Next, substrate scope study on aryl iodides was surveyed (Scheme 4). Iodobenzenes bearing either an electron-donating or electron-withdrawing group at the para-, meta-, or ortho-position were all found compatible with our catalytic system (3l–3ah). Surprisingly, ortho-methyl- and fluoro-substituted aryl iodides afforded the products in only trace amounts. However, aryl iodide with ortho-methoxy group provided the desired product 3ac in a moderate yield. Notably, a distinctive electronic effect pattern was not observed in the process. It should be mentioned that arylated products bearing halogen, ester, and cyano groups could be readily converted to other molecules, which significantly improves the synthetic applicability of the process. Delightfully, aryl iodide-containing natural products like ketoprofen, fenchol and menthol were proven compatible, supplying the corresponding products in moderate yields. Unfortunately, (hetero)aryl iodides including 2-iodopyridine, 3-iodopyridine, 4-iodopyridine and 4-iodo-2-chloropyridine failed to produce the corresponding products. Although our protocol provides a novel and direct pathway to construct β-arylated primary aliphatic aldehydes, the yields of most examples are modest. The leading reasons for this compromise are the following: (1) aliphatic aldehydes are easily decomposed or oxidized to acids; (2) some of the prepared β-arylated aldehyde products may be further transformed into the corresponding α,β-unsaturated aldehydes.Open in a separate windowScheme 4Scope of aryl iodides. Reaction conditions: 1a (0.2 mmol), 2 (0.4 mmol), Pd(OAc)2 (15 mol%), AgTFA (0.3 mmol), L1 (60 mol%), TDG1 (60 mol%), HFIP (1.8 mL), HOAc (0.2 mL), 100 °C, 12 h. Isolated yields.Density functional theory (DFT) calculations were performed to help investigate the reaction mechanism and to elucidate the role of the ligand in improving the reactivity (Fig. 2). The condensation of the aliphatic aldehyde 1a with the TDG to form imine-1a was found thermodynamically neutral (ΔG° = −0.1 kcal mol−1). As a result, it was permissible to use imine-1a directly in the calculations. According to the calculations results, the precatalyst [Pd(OAc)2]3, a trimeric complex, initially experiences dissociation and ligand metathesis with imine-1a to generate the Pd(ii) intermediate IM1, which is thermodynamically favorable by 21.9 kcal mol−1. Consequently, the deprotonated imine-1a couples to the bidentate ligand to form the stable six-membered chelate complex IM1. Therefore, IM1 is indeed the catalyst resting state and serves as the zero point to the energy profile. We have identified two competitive pathways for the Pd(ii)-catalyzed C–H activation starting from IM1, one of which incorporates L1 and another which does not. On the one hand, an acetate ligand substitutes one imine-1a chelator in IM1 to facilitate the subsequent C–H activation leading to IM2, which undergoes C(sp3)–H activation through concerted metalation-deprotonation (CMD) viaTS1 (ΔG = 37.4 kcal mol−1). However, this kinetic barrier is thought to be too high to account for the catalytic activity at 100 °C. On the other hand, the chelate imine-1a could be replaced by two N-coordinated ligands (L1) leading to the Pd(ii) complex IM3. This process is endergonic by 6.4 kcal mol−1. To allow the ensuing C–H activation, IM3 dissociates one ligand (L1) producing the active species IM4, which undergoes TS2 to cleave the β-C(sp3)–H bond and form the [5,6]-bicyclic Pd(ii) intermediate IM5. Although this step features an energy barrier of 31.2 kcal mol−1, it is thought to be feasible under the experimental conditions (100 °C). Possessing similar coordination ability to that of pyridine, the ligand (L1) effectively stabilizes the Pd(ii) center in the C–H activation process, indicating that this step most likely involves a manageable kinetic barrier. This result explicates the origin of the ligand-enabled reactivity (TS2vs.TS1). Additionally, we considered the γ-C(sp3)–H activation pathway viaTS2′ which was found to have a barrier of 35.5 kcal mol−1. The higher energy barrier of TS2′ compared to that of TS2 is attributed to its larger ring strain in the [6,6]-bicyclic Pd(ii) transition state, which reveals the motive for the site-selectivity. Reverting back to the supposed pathway, upon the formation of the bicyclic intermediate IM5, it undergoes ligand/substrate replacement to afford intermediate IM6, at which the Ar–I coordinates to the Pd(ii) center to enable oxidative addition viaTS3 (ΔG = 27.4 kcal mol−1) leading to the five-coordinate Pd(iv) complex IM7. Undergoing direct C–C reductive elimination in IM7 would entail a barrier of 29.6 kcal mol−1 (TS4). Alternatively, iodine abstraction by the silver(i) salt in IM7 is thermodynamically favorable and irreversible, yielding the Pd(iv) intermediate IM8 coordinated to a TFA ligand. Subsequently, C–C reductive coupling viaTS5 generates the Pd(ii) complex IM9 and concludes the arylation process. This step was found both kinetically facile (6.1 kcal mol−1) and thermodynamically favorable (30.7 kcal mol−1). Finally, IM9 reacts with imine-1avia metathesis to regenerate the palladium catalyst IM1 and release imine-3a in a highly exergonic step (21.0 kcal mol−1). Ultimately, imine-3a undergoes hydrolysis to yield the aldehyde product 3a and to release the TDG.Open in a separate windowFig. 2Free energy profiles for the ligand-promoted Pd(ii)-catalyzed site-selective C–H activation and C–C bond formation, alongside the optimized structures of the C–H activation transition states TS1 and TS2 (selected bond distances are labelled in Å). Energies are relative to the complex IM1 and are mass-balanced.  相似文献   
269.
应用薄层色谱法(TLC)使对硫膦中的主成分,o,o'-二甲基-对硝基苯基硫代膦酸酯(DMNPTP),与以杂质共存的二硝基与邻硝基衍生物分离.TLC法中用硅胶(G254)作吸附剂,用石油醚与乙酸乙酯(8 2)的混合物作为展开溶剂,经TCL分离后,用刀片将样品(含DMNPTP)的色谱带括下,经蒸发除去有机溶剂,用硝酸-高氯酸加热消化并蒸发至干后,用硝酸溶解残渣.此时,溶液中原来以DMNPTP存在的化合物已转化为正磷酸盐,随即用磷钒钼杂多酸光度法测定其磷含量,测定波长为其吸收峰450 nm,由测定值换算为DMNPTP的含量.  相似文献   
270.
Phase separation in cell membranes promotes the assembly of transmembrane receptors to initiate signal transduction in response to environmental cues. Many cellular behaviors are manipulated by promoting membrane phase separation through binding to multivalent extracellular ligands. However, available extracellular molecule tools that enable manipulating the clustering of transmembrane receptors in a controllable manner are rare. In the present study, we report a DNA nanodevice that enhances membrane phase separation through the clustering of dynamic lipid rafts. This DNA nanodevice is anchored in the lipid raft region of the cell membrane and initiated by ATP. In a tumor microenvironment, this device could be activated to form a long DNA duplex on the cell membrane, which not only enhances membrane phase separation, but also blocks the interaction between the transmembrane surface adhesion receptor and extracellular matrix, leading to reduced migration. We demonstrate that the ATP-activated DNA nanodevice could inhibit cancer cell migration both in vitro and in vivo. The concept of using DNA to regulate membrane phase separation provides new possibilities for manipulating versatile cell functions through rational design of functional DNA structures.

A DNA nanodevice is developed to enhance the cell membrane phase separation in a tumor microenvironment to weaken the formation of focal adhesion. As a result, the migration of cancer cells is inhibited both in vitro and in vivo.  相似文献   
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