Amino acid order in polymeric dipeptide surfactants: effect on physical properties and enantioselectivity.
Amino acid order in polymeric dipeptide surfactants: effect on physical properties and enantioselectivity.
复制标题
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。
DOI：
10.1021/ac980461r
复制
发表时间：
1999
影响因子：
7.4
通讯作者：
Warner,IM
中科院分区：
文献类型：
--
作者：
Billiot,E;Agbaria,RA;Thibodeaux,S;Shamsi,S;Warner,IM
研究了高分子二肽表面活性剂中氨基酸顺序对其手性选择性的影响，以及表面活性剂的物理性质。了解这种二肽表面活性剂的对映选择性对于设计更高效的聚合物表面活性剂至关重要，并且对其他研究领域也有影响，例如氨基酸基化合物（即酶、血红蛋白、抗体等）的对映选择性相互作用。应当注意的是，这种聚合表面活性剂不易结晶。因此，就像研究蛋白质一样，荧光光谱是研究这些高分子表面活性剂的结构-功能关系的有力工具。采用环境敏感探针芘和6-丙炔-2-（二甲氨基）萘（Prodan）对18种高分子表面活性剂的核内微环境进行了表征。本研究中检测的表面活性剂包括所有可能的丙氨酸、缬氨酸和亮氨酸的二肽组合，以及非手性氨基酸甘氨酸（甘氨酸-甘氨酸除外），以及丙氨酸、缬氨酸和亮氨酸的单氨基酸表面活性剂。荧光探针研究的结果提出了溶液中聚合物二肽表面活性剂的结构。采用毛细管电动色谱法，用（±）1,1′-双-2-萘酚和（±）1,1′-双-2-萘-2,2′-磷酸氢二酯两种模型对所提结构的手性选择性进行了测试。
The effect of amino acid order on chiral selectivity in polymeric dipeptide surfactants, as well as the physical properties of the surfactants, is investigated. An understanding of enantioselectivity of such dipeptide surfactants is crucial to the design of more efficient polymeric surfactants and has implications in other areas of research such as enantioselective interactions of amino acid based compounds (i.e., enzymes, hemoglobin, antibodies, etc.). It should be noted that such polymeric surfactants are not easily crystallized. Therefore, in a manner similar to the study of proteins, fluorescence spectroscopy is a powerful tool used to study the structure−function relationship of these polymeric surfactants. The microenvironments inside the core of 18 polymeric surfactants were characterized using the environmentally sensitive probes pyrene and 6-propionyl-2-(dimethylamino)naphthalene (Prodan). The surfactants examined in this study include all possible dipeptide combinations of thel-form of alanine, valine, and leucine and the achiral amino acid glycine (except glycine-glycine) as well as the single amino acid surfactants of alanine, valine, and leucine. The results of the fluorescent probe studies led to a proposed structure of the polymeric dipeptide surfactants in solution. The implications of the proposed structure for chiral selectivity were tested with two model atropisomers, (±)1,1‘-bi-2-naphthol and (±)1,1‘-bi-2-naphthyl-2,2‘-diyl hydrogen phosphate, using capillary electrokinetic chromatography.