Süss F, Poppitz W, Sänger-van de Griend C E, Scriba G K
Department of Pharmaceutical Chemistry, University of Jena, School of Pharmacy, Germany.
Electrophoresis. 2001 Aug;22(12):2416-23. doi: 10.1002/1522-2683(200107)22:12<2416::AID-ELPS2416>3.0.CO;2-S.
The separation of dipeptide and tripeptide enantiomers using negatively charged single isomers as well as randomly sulfated and sulfonated cyclodextrins (CDs) was investigated with respect to the amino acid sequence of the peptides and the nature of the CDs. Standardized conditions concerning buffer pH and molarity, CD concentration, and separation voltage were applied. Compared to suffobutylether-beta-CD and heptakis-(2,3-dimethyl-6-sulfato)-beta-CD, randomly sulfated beta-CD as well as the single isomer derivatives heptakis-6-sulfato-beta-CD and heptakis-(2,3-diacetyl-6-sulfato)-beta-CD were the more universal CDs for enantioseparations. The enantiomer migration order depended to a greater extent on the CD than on the amino acid sequence of the peptide although small structural differences such as formation of a peptide amide or ester affected the chiral recognition by the randomly substituted CD derivatives. Using sulfobutylether-beta-CD or heptakis-(2,3-diacetyl-6-sulfato)-beta-CD the DD enantiomers migrated before the LL enantiomers for most peptides while the opposite migration order, i.e. LL before DD, was observed when heptakis-6-sulfato-beta-CD was applied as chiral selector.
使用带负电荷的单一异构体以及随机硫酸化和磺化的环糊精（CDs）对二肽和三肽对映体进行分离，并针对肽的氨基酸序列和CDs的性质进行了研究。应用了关于缓冲液pH值和摩尔浓度、CD浓度以及分离电压的标准化条件。与磺丁基醚-β-环糊精和七（2,3-二甲基-6-硫酸根）-β-环糊精相比，随机硫酸化的β-环糊精以及单一异构体衍生物七（6-硫酸根）-β-环糊精和七（2,,3-二乙酰基-6-硫酸根）-β-环糊精是对映体分离中更通用的环糊精。对映体迁移顺序在更大程度上取决于环糊精，而不是肽的氨基酸序列，尽管诸如肽酰胺或酯的形成等小的结构差异会影响随机取代的环糊精衍生物的手性识别。使用磺丁基醚-β-环糊精或七（2,3-二乙酰基-6-硫酸根）-β-环糊精时，对于大多数肽，DD对映体在LL对映体之前迁移，而当使用七（6-硫酸根）-β-环糊精作为手性选择剂时，观察到相反的迁移顺序，即LL在DD之前。
