Chen Hongxia, Cheng Haiyun, Lee Jaebeom, Kim Jae-Ho, Hyun Myung Ho, Koh Kwangnak
College of Pharmacy, Pusan National University, Pusan 609-735, Republic of Korea.
Talanta. 2008 Jun 30;76(1):49-53. doi: 10.1016/j.talanta.2008.02.001. Epub 2008 Feb 15.
Pirkle-type chiral stationary phases (CSPs) showed excellent enantiomeric separation for amino acid derivatives by forming energetically different two transient diastereomeric pi-pi donor-acceptor complexes with two enantiomers. A CSP derived from N-(3,5-dinitrobenzoyl) leucine with a thiol ending group for immobilization on Au was synthesized and self-assembled on Au surface as chiral sensing layer. The monolayer characterized by spectroscopic and microscopic methods such as AFM, FTIR reflection absorption spectroscopy (FTIR-RAS) and cyclic voltammetry (CV). The enantiospecific detection onto CSP of the leucine derivative was studied by surface plasmon resonance (SPR). (S)-CSP SAM showed high chiral differential detection for (S)-analyte in a range of 1.0x10(-9) to 1.0x10(-4) M. In combination with the SPR method, the leucine derivative monolayer provided a reliable and simple experimental platform for enantiospecific detection.
皮尔克型手性固定相（CSPs）通过与两种对映体形成能量不同的两种瞬态非对映体π-π供体-受体络合物，对氨基酸衍生物表现出优异的对映体分离能力。合成了一种衍生自N-（3,5-二硝基苯甲酰基）亮氨酸且带有用于固定在金上的硫醇端基的CSP，并将其作为手性传感层自组装在金表面。通过原子力显微镜（AFM）、傅里叶变换红外反射吸收光谱（FTIR-RAS）和循环伏安法（CV）等光谱和显微镜方法对该单分子层进行了表征。通过表面等离子体共振（SPR）研究了亮氨酸衍生物在CSP上的对映体特异性检测。（S）-CSP自组装单分子膜对（S）-分析物在1.0×10⁻⁹至1.0×10⁻⁴ M范围内表现出高对映体差异检测能力。结合SPR方法，亮氨酸衍生物单分子层为对映体特异性检测提供了一个可靠且简单的实验平台。
