Comprehensive Synthesis of Monohydroxy–Cucurbit[n]urils (n = 5, 6, 7, 8): High Purity and High Conversions

Abstract

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Can we beat the biotin–avidin pair?: cucurbit[7]uril-based ultrahigh affinity host–guest complexes and their applications

“…97 This approach involves the condensation of an acyclic glycoluril hexamer with glycoluril bis-(cyclic ethers) to produce monofunctionalized CB [7] which can be further transformed into tailor-made CB [7] derivatives for various applications. 98 This method relying on a controlled generation of hydroxyl radicals from hydrogen peroxide seems useful in the rapid generation of monohydroxy derivatives of the main members of the CB[n] family in high yield (490%). 98 This method relying on a controlled generation of hydroxyl radicals from hydrogen peroxide seems useful in the rapid generation of monohydroxy derivatives of the main members of the CB[n] family in high yield (490%).…”

Mono‐, Di‐, and Tri‐Hydroxylated Symmetrical Hexamethylcucurbit[3,3]uril and Allylated Derivatives

“…In recent work, we successfully prepared mono-and dihydroxylated OMeQ [6] using the method published by Bardelang and Ouari, [18,19] and fortunately we obtained the major trans-di-hydroxylated OMeQ [6] isomer. [21][22][23][24] For the symmetrical hexamethylcucurbit [3,3]uril (Me 6 Q [3,3]), the most valuable hydroxylated product could be the trihydroxylated {(OH) 3 Me 6 Q[3,3]}, which may be further modified at its three meta-positions and thus in three directions.…”

“…Moreover, (HO) 2n Q[n]s are not suitable for precise or targeted modification due to their many reactive sites. [17] Since Bardelang and Ouari developed a mild photochemical method to directly introduce limited hydroxyl groups on cucurbit[n]urils (n = 5, 6, 7, 8) using hydrogen peroxide and then UV light, [18,19] this method [3,3]uril (Me 6 Q [3,3]). For example, Isaacs and co-workers reacted C-type oligomers with a functionalized glycoluril to afford monofunctional Q[n]s, [12][13][14][15] Scherman and co-workers prepared monohydroxylated Q [6] [16] using a modified method described by Kim, [2] and Kim and co-workers recently prepared monohydroxylated Q [7] by introducing excess K 2 SO 4 to balance the oxidation of Q [7].…”

Supramolecular hydrogels encapsulating bioengineered mesenchymal stem cells for ischemic therapy

“…To achieve the high crosslinking density and facile synthesis, we carried out mono-functionalization of CB [6], which is a big challenge for various biomedical applications 19,20 ( Fig. 1A).…”

“…Despite the great effort to introduce functional moieties on CB [6], 21 mono-amination of CB [6] is still difficult and complicated. 22,23 We previously reported the method to synthesize CB [6]-HA derivative via Michael addition between thiol (SH) modied HA and mono-allyloxy CB [6]. However, there were unreacted thiol groups on HA backbone, resulting in selfcrosslinking by disulde bonding.…”