Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing
Abstract
:1. Introduction
1.1. General Considerations
1.2. Chiral recognition principle
- ▪
- “An essential requirement is that the chiral macrocycles form reasonably stable complexes with the guest enantiomers so that the repulsive interactions can effectively lessen the stability of the complex of one enantiomer.
- ▪
- Large chiral barrier(s) result in a high degree of enantiomeric recognition.
- ▪
- Low conformational flexibility of diastereomeric complexes plays an important role in good enantiomeric recognition. Two factors, rigid macrocycles and multipoint interactions, ensure a fixed conformation of the complexes.
- ▪
- The structural complementarity between chiral macrocycles and enantiomers ensures that the chiral barriers of macrocycles make full use of steric repulsion for enantiomeric recognition.
- ▪
- Macrocyclic receptors possessing C2, C3, and D2 symmetry usually show higher enantioselectivity than those of C1 and D3 symmetry”
1.3. Scope of the review
2. Cyclodextrins for Chiral Sensing
2.1. Generalities
2.2. Chiral recognition properties of cyclodextrins
2.3. Cyclodextrins in chiral sensing layer
2.3.1. Chiral sensing at the solid-liquid interface
2.3.2. In the gas phase
3. Other chiral macrocycles, potential candidates for chiral sensing
3.1. Calixarenes and Calix-resorcinarenes
3.2. Crown-ethers
4. Concluding remarks
References and Notes
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Alpha | Beta | Gamma | |
---|---|---|---|
Glucose monomers | 6 | 7 | 8 |
Molecular weight | 972 | 1135 | 1297 |
Height of torus, Å | 7.9 | 7.9 | 7.9 |
Internal cavity volume, Å3 | 174 | 262 | 427 |
Internal cavity diameter, Å | 4.7-5.3 | 6.0-6.5 | 8 |
[α]D 25°C | 150 | 162 | 177 |
Water solubility (g/100mL: 25° C) | 14.2 | 1.85 | 23.2 |
Water molecules in cavity | 6 | 11 | 17 |
Ref | n | R1 | R2 | R3 | Guest | Sensing method |
---|---|---|---|---|---|---|
[47] | 6 | octyl | Octyl, H | O-octyl | ephedrine | Potentiometric |
[48] | 6 | octyl | octyl | O-octyl | ehedrine | Potentiometric |
[49] | 6 | H, Me, Ac or Octyl | Octyl | O-octyl | Ephedrinium ion | Potentiometric |
[50] | Octyl | octyl or dodecyl | O-octyl or O-dodecyl | amphetamine propanalol | Potentiometric | |
[51] | 7 | trimethylammoniopropyl | H | OH | ramipril | Potentiometric |
[52] | 7 | trimethylammoniopropyl | H | OH | cilazapril pentopril trandolapril | Potentiometric |
[53] | 6, 7 or 8 | H | H | OH | perindopril | Potentiometric |
[54] | 7 | trimethylammoniopropyl | H | OH | perindopril | Potentiometric |
[55] | 7 | trimethylammoniopropyl | H | OH | proline | Potentiometric |
[56] | 7 | H | H | NH-CO-(CH2)nS(CH2)-nCH3 | thyroxine | SPR |
[57] | 6 | H | H | NH(CH2)2SH | Phenyl-ethylamine | CV |
[58] | 6 | H | H | NH(CH2)2SH | DOPA-derivatives | CV |
n | R1 | R2 | R3 | Guest | Sensing method |
---|---|---|---|---|---|
6,7,8 | Me | Me, pentyl | O-Me | citronellal rose oxide | QCM |
7 | Ethyl, methyl, acetyl | Ethyl, methyl, acetyl | TBDMS | limonene | QCM |
7, 8 | pentyl | pentyl | O-Me | Pinene pinane | QCM |
7 | Me, Pentyl, φCHO | Me, Pentyl, φCHO | mono-ONHCONH(CH2)nSH | methyl-lactate | QCM |
7 | (OMe)6 ONHCONH(CH2)nSH n= 2, 6 or 11 | 2-butanol 2-octanol methyl-lactate ethyl-lactate carvone | QCM | ||
7 | pentyl | Butanoyl | O-pentyl | Methyl lactate Methyl chloropropionate | SAW |
8 | pentyl | butanoyl | O-pentyl | Sevoflurane degradation product | TSMR, SAW, SPR |
8 | butanoyl | pentyl | O-pentyl | methyl-lactate methyl-chloropropionate flurane derivatives | SMR |
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Shahgaldian, P.; Pieles, U. Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing. Sensors 2006, 6, 593-615. https://doi.org/10.3390/s6060593
Shahgaldian P, Pieles U. Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing. Sensors. 2006; 6(6):593-615. https://doi.org/10.3390/s6060593
Chicago/Turabian StyleShahgaldian, Patrick, and Uwe Pieles. 2006. "Cyclodextrin Derivatives as Chiral Supramolecular Receptors for Enantioselective Sensing" Sensors 6, no. 6: 593-615. https://doi.org/10.3390/s6060593