Advances in chiral separations of small peptides by capillary electrophoresis and chromatography

被引:124
作者
Ali, Imran [1 ]
Al-Othman, Zeid A. [2 ]
Al-Warthan, Abdulrahman [2 ]
Asnin, Leonid [3 ]
Chudinov, Alexander [3 ]
机构
[1] Cent Univ, Jamia Millia Islamia, Dept Chem, New Delhi, India
[2] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia
[3] Perm Natl Res Polytech Univ, Perm, Russia
关键词
Capillary electrophoresis; Chiral recognition mechanisms; Chiral separation; Hybrid techniques; Peptides; HOST-GUEST COMPLEXATION; PERFORMANCE LIQUID-CHROMATOGRAPHY; AMINO-ACID-SEQUENCE; CARBOXYMETHYL-BETA-CYCLODEXTRIN; PARTICLE-LOADED MONOLITHS; PARTIAL FILLING TECHNIQUE; MOBILE-PHASE-COMPOSITION; STATIONARY PHASES; CROWN-ETHER; ENANTIOMERIC SEPARATION;
D O I
10.1002/jssc.201400587
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Many chemical and biological processes are controlled by the stereochemistry of small polypeptides (di-, tri-, tetra-, penta-, hexapeptides, etc). The biological importance of peptide stereoisomers is of great value. Therefore, the chiral resolution of peptides is an important issue in biological and medicinal sciences and drug industries. The chiral resolutions of peptide racemates have been discussed with the use of capillary electrophoresis and chromatographic techniques. The various chiral selectors used were polysaccharides, cyclodextrins, Pirkle types, macrocyclic antibiotics, crown ethers, imprinted polymers, etc. The stereochemistry of dipeptides is also discussed. Besides, efforts are made to explain the chiral recognition mechanisms, which will be helpful in understanding existing and developing new stereoselective analyses. Future perspectives of enantiomeric resolution are also predicted. Finally, the review concludes with the demand of enantiomeric resolution of all naturally occurring and synthetic peptides.
引用
收藏
页码:2447 / 2466
页数:20
相关论文
共 201 条
[1]  
Aboul-Enein H.Y., 2003, Chiral separation by liquid chromatography and related technologies
[2]   High-performance liquid chromatographic enantioseparation of drags containing multiple chiral centers on polysaccharide-type chiral stationary phases [J].
Aboul-Enein, HY .
JOURNAL OF CHROMATOGRAPHY A, 2001, 906 (1-2) :185-193
[3]   Molecular imprinting of cyclodextrin on silica-gel support for the stationary phase of high-performance-liquid-chromatography [J].
Akiyama, T ;
Hishiya, T ;
Asanuma, H ;
Komiyama, M .
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2001, 41 (1-4) :149-153
[4]   Chiral separation of β-adrenergic blockers on CelluCoat column by HPLC [J].
Ali, Imran ;
Gaitonde, Vinay D. ;
Aboul-Enein, Hassan Y. ;
Hussain, Afzal .
TALANTA, 2009, 78 (02) :458-463
[5]   MOLECULAR RECOGNITION IN SYNTHETIC-POLYMERS - PREPARATION OF CHIRAL STATIONARY PHASES BY MOLECULAR IMPRINTING OF AMINO-ACID AMIDES [J].
ANDERSSON, LI ;
OSHANNESSY, DJ ;
MOSBACH, K .
JOURNAL OF CHROMATOGRAPHY, 1990, 513 :167-179
[6]   Molecular imprinting of the endogenous neuropeptide Leu(5)-enkephalin and some derivatives thereof [J].
Andersson, LI ;
Muller, R ;
Mosbach, K .
MACROMOLECULAR RAPID COMMUNICATIONS, 1996, 17 (01) :65-71
[7]  
[Anonymous], 1999, HDB GUID US MACR GLY
[8]  
[Anonymous], 1992, FDA POL STAT DEV NEW
[9]   SEPARATION OF DRUG STEREOISOMERS BY THE FORMATION OF BETA-CYCLODEXTRIN INCLUSION COMPLEXES [J].
ARMSTRONG, DW ;
WARD, TJ ;
ARMSTRONG, RD ;
BEESLEY, TE .
SCIENCE, 1986, 232 (4754) :1132-1135
[10]   MACROCYCLIC ANTIBIOTICS AS A NEW CLASS OF CHIRAL SELECTORS FOR LIQUID-CHROMATOGRAPHY [J].
ARMSTRONG, DW ;
TANG, YB ;
CHEN, SS ;
ZHOU, YW ;
BAGWILL, C ;
CHEN, JR .
ANALYTICAL CHEMISTRY, 1994, 66 (09) :1473-1484