The Breaking of Symmetry Leads to Chirality in Cucurbituril-Type Hosts
Abstract
:1. Introduction
2. Chiral Cucurbituril-Type Hosts
3. Breaking Symmetry through Complex Formation with Achiral Compounds
4. Breaking Symmetry through Complex Formation with Chiral Compounds
5. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Legend | Structure of Guest, Name of Host and Reference Number | ||
---|---|---|---|
G | | | |
H | CB[8] | CB[8] | CB[7] |
Ref. | [66] | [66] | [69] |
G | | | |
H | CB[7] | ||
Ref. | [69] | ||
G | | | |
H | CB[7] | ||
Ref. | [70] | ||
G | | | |
H | CB[7] | ||
Ref. | [70] | ||
G | | | |
H | CB[7] | ||
Ref. | 70 | ||
G | | | |
H | CB[7] | ||
Ref. | [70] |
Legend | Structure of Guest, Name of Host and Reference Number | ||
---|---|---|---|
G | | | |
Paclitaxel | Docetaxel | Fulvestrant | |
H | Acyclic CB | ||
Ref. | [71] | ||
G | | | |
Itraconazole | Voriconazole | ||
H | Acyclic CB | ||
Ref. | [71] | ||
G | | | |
α-ethynylestradiol | Estradiol | PBS 1086 | |
H | Acyclic CB | ||
Ref. | [71,72,73] | ||
G | | | |
S-camptothecin | Melphalan | 2-methoxyestradiol | |
H | Acyclic CB, CB[7], CB[8] | Acyclic CB | Acyclic CB |
Ref. | [71,72,73,74,75,76,77] | [71,72,73] | [73] |
G | | | |
Rocuronium | Vecuronium | Pancuronium | |
H | Acyclic CB | ||
Ref. | [78] | ||
G | | | |
Cisatracurium | Tubocurarine | ||
H | Acyclic CB | ||
Ref. | [78] | ||
G | | | |
Labetalol | Phenylephrine | ||
H | CB[7] | CB[6], Acyclic CB | |
Ref. | [79] | [80] | |
G | | | |
Pseudoephedrine | Adrenaline | Amphetamine hydrochloride | |
H | CB[6], Acyclic CB | CB[6] | CB[7] |
Ref. | [80] | [81] | [82] |
G | | | |
Methamphetamine hydrochloride | Prilocaine | Sodium ascorbate | |
H | CB[7] | CB[7] | CB[6] |
Ref. | [82] | [83] | [84] |
G | | | |
Pilocarpine | 6-monoacetymorphine | Noroxycodone | |
H | CB[7] | Acyclic CB | Acyclic CB |
Ref. | [85] | [86] | [86] |
G | | | |
Morphine | Heroin | Oxycodone | |
H | Acyclic CB | ||
Ref. | [86] | ||
G | | | |
Normorphine | Morphine-6-glucuronide | Oxymorphone | |
H | Acyclic CB | ||
Ref. | [86] | ||
G | | | |
Penicillin G | (S)-propranolol | Ampicillin | |
H | CB[8] | ||
Ref. | [66] | ||
G | | | |
(S)-1-phenylethanol | Tropicamide | ||
H | CB[8] | CB[7], CB[8] | |
Ref. | [66] | [87] |
Legend | Structure of Guest, Name of Host and Reference Number | ||
---|---|---|---|
G | | | |
H | CB[6], Acyclic CB | CB[6], Acyclic, CB[7], iCB[7] | CB[6], Acyclic, CB[7], iCB[7] |
Ref. | [88] | [82,89,90,91,92] | [82,89,90,91,92] |
G | | | |
H | CB[6], CB[7], CB[8], iCB[7] | CB[6], CB[7], CB[8], iCB[7] | CB[6], CB[7], CB[8], iCB[7] |
Ref. | [82,89,91,93,94] | [89,91,92,93,94,95,96] | [89,92,93,94] |
G | | | |
H | iCB[7], CB[6] | iCB[7] | iCB[7] |
Ref. | [91,97] | [91] | [91] |
G | | | |
H | iCB[7], CB[7] | iCB[7], CB[7] | CB[7] |
Ref. | [91,92] | [91,92] | [92] |
G | | | |
H | CB[7] | ||
Ref. | [92] | ||
G | | | R = H , CH3 ; R´ = CH3 , Cl |
H | CB[7] | CB[8] | |
Ref. | [92] | [98] | |
G | | | |
H | CB[7] | ||
Ref. | [66] | ||
G | | | |
H | CB[6], Acyclic CB | CB[6], Acyclic CB | CB[8] |
Ref. | [88] | [88] | [94] |
G | | | |
H | CB[8] | CB[7], CB[6] | CB[6],CB[8], iCB[7] |
Ref. | [94] | [99] | [91,94,100,101] |
G | Phe-Gly Phe-Ala Phe-Val Gly-Ala Asp-Phe Hippuryl-Phe | TrpPro Trp-OMe NAc-Trp Aspartame NAcTrp-NH2 Trp(Pro)6-NH2 Trp(Gly)6-NH2 | Trp(Ala)6-NH2 Trp(Val)6-NH2 Trp(Leu)6-NH2 Trp(Asp)6-NH2 Trp(Glu)6-NH2 5-F-Trp(Gly)6-NH2 5-F-Trp(Asn)6-NH2 |
H | CB[8] | ||
Ref. | [66] | ||
G | Phe-Gly-Gly Gly-Phe-Gly Gly-Gly-Phe Gly-Gly-Trp-Gly-Gly | His-Gly-Gly Gly-His-Gly Gly-Gly-His Gly-Gly-Tyr Tyr-Gly-Gly | Gly-Tyr Gly-Trp Gly-Gly |
H | CB[8] | CB[8] | CB[6] |
Ref. | [102] | [102] | [103] |
G | Gly-Tyr-Gly | Trp-Gly-Gly | Gly-Gly-Trp |
H | CB[8] | CB[8] | CB[8] |
Ref. | [102,104] | [94,102,104] | [94,102] |
G | | Thr-Gly-Ala-Phe-Met Thr-Gly-Ala-AMPhe-Met | Phe-Leu Phe-Met-NH2 Phe-Leu-NH2 Thr-Gly-Ala-Phe-Leu Thr-Gly-Ala-Phe-Met-NH2 Thr-Gly-Ala-Phe-Leu-NH2 Thr-Gly-Ser-Phe-Met-NH2 Thr-Gly-Gly-Phe-Met-NH2 Thr-Gly-DAla-Phe-Met-NH2 |
H | CB[8] | CB[7] | CB[7] |
Ref. | [105] | [106] | [96] |
G | Gly-Phe | ||
H | CB[8], CB[6] | ||
Ref. | [51,88] |
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Aav, R.; Mishra, K.A. The Breaking of Symmetry Leads to Chirality in Cucurbituril-Type Hosts. Symmetry 2018, 10, 98. https://doi.org/10.3390/sym10040098
Aav R, Mishra KA. The Breaking of Symmetry Leads to Chirality in Cucurbituril-Type Hosts. Symmetry. 2018; 10(4):98. https://doi.org/10.3390/sym10040098
Chicago/Turabian StyleAav, Riina, and Kamini A. Mishra. 2018. "The Breaking of Symmetry Leads to Chirality in Cucurbituril-Type Hosts" Symmetry 10, no. 4: 98. https://doi.org/10.3390/sym10040098