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1、2008年第66卷化学学报Vol.66,2008第17期,1974~1978ACTACHIMICASINICANo.17,1974~1978·研究论文·手性固定相Chirex3001对安息香和联萘酚及其类似物的分子识别a,b,a,cba,c尤秀丽韩大雄*翁文赵玉芬a(厦门大学化学化工学院化学生物学福建省重点实验室厦门361005)b(漳州师范学院化学与环境科学系漳州363000)c(厦门大学医学院药学系厦门361005)摘要利用分子力学方法,建立了苯基甘氨酸型手性固定相Chirex3001的简化模型,并探讨了手性固定相Chirex3001与安息
2、香和联萘酚及其类似物的识别机制.模拟结果表明,固定相主体与手性客体分子识别作用的推动力主要来自于它们之间的π-π堆积、氢键和范德华等作用.主体与(S)-构型的客体1~3结合能力强于(R)-构型的客体,而对于客体4~6,则是与(R)-构型的结合强于(S)-构型,这与高效液相色谱拆分实验结果相符.客体1~3对映体在Chirex3001柱上的分离因子分别为1.02,1.04和1.11,(R)-构型先被洗脱;客体4~6对映体的分离因子分别为1.23,1.26和1.09,(S)-构型先被洗脱.关键词手性识别;分子力学;手性拆分;安息香;联萘酚Molecu
3、larRecognitionofBenzoinandBi-β-naphtholAnaloguesbyChirex3001-basedChiralStationaryPhaseYOU,Xiu-Lia,bHAN,Da-Xiong*,a,cWENG,WenbZHAO,Yu-Fena,ca(TheKeyLaboratoryforChemicalBiologyofFujianProvince,DepartmentofChemistry,XiamenUniversity,Xiamen361005)b(DepartmentofChemistryandEnvi
4、ronmentalScience,ZhangzhouNormalUniversity,Zhangzhou363000)c(DepartmentofPharmacy,MedicalCollege,XiamenUniversity,Xiamen361005)AbstractThesimplifiedmodelof(R)-phenylglycinebasedchiralstationaryphase(Chirex3001)wasbuilttoinvestigatetheprocessofchiralrecognitionofbenzoinandbi-
5、β-naphtholandtheiranaloguesbymolecu-larmechanicsmethods.Theresultsshowedthatthedrivingforceofchiralrecognitioncamefromtheπ-πstacking,hydrogenbondandvanderWaalsinteractionsbetweenthehostandtheguestmolecule.ThehostpreferredtobindwithS-enantiomersofbenzoinanditsanalogues1~3,and
6、preferredtobindwithR-enantiomersofbi-β-naphtholanditsanalogues4~6.ThiswasconsistentwiththeHPLCexperimentalresults.Theseparationfactorswere1.02,1.04and1.11respectivelyforcompounds1~3whenn-hexane/1,2-dichloroethane/ethanol(V∶V∶V=83.5∶15∶1.5)wasusedasmobilephase,andtheR-enantio
7、merswereelutedfirst.Theseparationfactorswere1.23,1.26and1.11respectivelywhenn-hexane/chloroform/ethanol(V∶V∶V=78.5∶20∶1.5)wasusedasmobilephase,andtheS-enantiomerswereelutedfirst.Keywordschiralrecognition;molecularmechanics;chiralresolution;benzoin;bi-β-naphthol[1]苯基甘氨酸型手性固定相
8、Chirex3001(图1a)是Pirkle型固定相的一种.这类固定相在手性液相色谱*E-mail:daxiong@xmu.edu.cnReceive