NMR characterization of 1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate binding to chiral molecular micelles
NMR characterization of 1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate binding to chiral molecular micelles
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1,1-联萘-2,2-二基磷酸氢盐与手性分子胶束结合的核磁共振表征
DOI：
10.1002/mrc.2561
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发表时间：
2010
影响因子：
2
通讯作者：
K. Morris
中科院分区：
文献类型：
--
作者：
Stephanie Kingsbury;Curtis J. Ducommun;Bryan M. Zahakaylo;Elizabeth H. Dickinson;K. Morris
用核磁共振波谱法研究了手性化合物1，1 ′-联萘-2，2 ′-磷酸氢二酯（BNP）与5种手性二肽分子胶束的结合.分子胶束在表面活性剂单体之间具有共价键，并且在电动色谱中用作手性移动的相改性剂。（S）-BNP：分子胶束混合物的核奥弗豪泽增强光谱（NOESY）分析显示，在每种溶液中，（S）-BNP主要与分子胶束二肽头基的N-末端氨基酸相互作用。NOESY光谱还用于生成（S）-BNP：分子胶束混合物的基团结合图谱。在这些图谱中，将百分比分配给（S）-BNP质子，以表示其与特定分子胶束质子相互作用的相对强度。所有图谱显示，（S）-BNP插入到先前报道的分子胶束的二肽头基和烃链之间形成的手性凹槽中。在所得的分子间复合物中，发现离分析物磷酸基团最近的（S）-BNP质子指向分子胶束头基的N-末端Hα质子。最后，脉冲场梯度NMR扩散实验用于测量（R）和（S）-BNP与每个分子胶束结合的缔合常数。然后使用这些K值计算对映异构体结合自由能的差异Δ（ΔG）。发现NMR衍生的Δ（ΔG）值与文献中的电动色谱（EKC）手性选择性线性成比例。版权所有© 2010约翰威利父子有限公司.
NMR spectroscopy was used to characterize the binding of the chiral compound 1,1′‐binaphthyl‐2,2′‐diyl hydrogen phosphate (BNP) to five molecular micelles with chiral dipeptide headgroups. Molecular micelles have covalent linkages between the surfactant monomers and are used as chiral mobile phase modifiers in electrokinetic chromatography. Nuclear overhauser enhancement spectroscopy (NOESY) analyses of (S)‐BNP:molecular micelle mixtures showed that in each solution the (S)‐BNP interacted predominately with the N‐terminal amino acid of the molecular micelle's dipeptide headgroup. NOESY spectra were also used to generate group binding maps for (S)‐BNP:molecular micelle mixtures. In these maps, percentages are assigned to the (S)‐BNP protons to represent the relative strengths of their interactions with a specified molecular micelle proton. All maps showed that (S)‐BNP inserted into a previously reported chiral groove formed between the molecular micelle's dipeptide headgroup and hydrocarbon chain. In the resulting intermolecular complexes, the (S)‐BNP protons nearest to the analyte phosphate group were found to point toward the N‐terminal Hα proton of the molecular micelle headgroup. Finally, pulsed field gradient NMR diffusion experiments were used to measure association constants for (R) and (S)‐BNP binding to each molecular micelle. These K values were then used to calculate the differences in the enantiomers' free energies of binding, Δ(ΔG). The NMR‐derived Δ(ΔG) values were found to scale linearly with electrokinetic chromatography (EKC) chiral selectivities from the literature. Copyright © 2010 John Wiley & Sons, Ltd.
两种手性聚合物表面活性剂与模型物质苯硫内酰脲氨基酸相互作用的表征和热力学研究。
影响因子：
7.4
作者：
Yarabe,HH;Shamsi,SA;Warner,IM
通讯作者：
Warner,IM
影响因子：
15
作者：
McCarroll, ME;Billiot, FH;Warner, IM
通讯作者：
Warner, IM
聚合二肽表面活性剂中的氨基酸顺序：对物理性质和对映选择性的影响。
影响因子：
7.4
作者：
Billiot,E;Agbaria,RA;Thibodeaux,S;Shamsi,S;Warner,IM
通讯作者：
Warner,IM