Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors

Destecroix, Harry; Renney, Charles M.; Mooibroek, Tiddo J.; Carter, Tom S.; Stewart, Patrick F. N.; Crump, Matthew P.; Davis, Anthony P.

doi:10.1002/anie.201409124

Cited by 66 publications

(45 citation statements)

References 38 publications

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“…We have previously described synthetic lectins that bind all‐equatorial monosaccharides (glucose and close relatives) with affinities from approximately 10 to 600 m −1 . A particular target has been the β‐ N ‐acetylglucosaminyl (β‐GlcNAc or O‐GlcNAc) unit 1 .…”

Section: Figurementioning

confidence: 99%

“…A 1,3,6,8‐tetrasubstituted pyrene is geometrically equivalent to the biphenyls in 4 , so tricyclic cage 5 was identified as a promising design. Based on recent work, receptor 5 was provided with more powerful water‐solubilizing groups than 4 ; pyrenes are strongly inclined to self‐associate in water, and this needed to be countered for reliable binding characterization.…”

Section: Figurementioning

confidence: 99%

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Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives

et al. 2016

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The combination of ap yrenyl tetraamine with an isophthaloyl spacer has led to two new water-soluble carbohydrate receptors ("synthetic lectins"). Both systems show outstanding affinities for derivatives of N-acetylglucosamine (GlcNAc) in aqueous solution. One receptor binds the methyl glycoside GlcNAc-b-OMe with K a % 20 000 m À1 , whereas the other one binds an O-GlcNAcylated peptide with K a % 70 000 m À1 .T hese values substantially exceed those usually measured for GlcNAc-binding lectins.S low exchange on the NMR timescale enabled structural determinations for several complexes.A se xpected, the carbohydrate units are sandwiched between the pyrenes,w ith the alkoxy and NHAc groups emerging at the sides.T he high affinity of the GlcNAcyl-peptide complex can be explained by extra-cavity interactions,r aising the possibility of af amily of complementary receptors for O-GlcNAc in different contexts.

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Section: Figurementioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives

et al. 2016

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“…Groups Z could be used to confer water‐solubility as well as to provide polar interactions. For example, polyionic dendrimers, which are highly water solubilizing and capable of hydrogen bonding to polar carbohydrate substituents, could be readily installed …”

Section: Figurementioning

confidence: 99%

Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water

et al. 2016

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Biomimetic carbohydrate receptors ("synthetic lectins") have potential as agents for biological researcha nd medicine.H owever,a lthough effective strategies are available for "all-equatorial" carbohydrates (glucose,e tc.), the recognition of other types of saccharide under natural (aqueous) conditions is less well developed. Herein we report an ew approach based on ap yrene platform with polar arches extending from aryl substituents.The receptors are compatible with axially substituted carbohydrates,a nd also feature two identical binding sites,t hus mimicking the multivalency observed for natural lectins.Avariant with negative charges forms 1:2h ost/guest complexes with aminosugars,w ith K 1 > 3000 m À1 for axially substituted mannosamine,w hereas ap ositively charged version binds the important a-sialyl unit with K 1 % 1300 m À1 .

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“…Davis and co‐workers achieved remarkable levels of affinity and selectivity in the binding of carbohydrates in water using “temple” receptors . These synthetic receptors were rationally designed following the guidelines discussed above.…”

Section: Introductionmentioning

confidence: 99%

Super Aryl‐Extended Calix[4]pyrroles: Synthesis, Binding Studies, and Attempts To Gain Water Solubility

Escobar

Aragay

Ballester

2016

Chemistry A European J

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We describe the synthesis of unprecedented calix[4]pyrrole receptors featuring "super aryl extended" (SAE) cavities. We elaborated the aromatic cavity provided by the αααα-isomer of para-tetraiodo-meso-phenyl calix[4]pyrrole by installing ethynyl-aryl substituents at its upper rim. We report the binding properties of the prepared SAE-calix[4]pyrrole tetraester towards pyridyl-N-oxides. The binding data revealed the formation of thermodynamically and kinetically highly stable 1:1 complexes. The complexation-induced chemical shifts indicated the formation of hydrogen bonds and aromatic interactions with the calix-core adopting the cone conformation. We quantified the additional interactions established between the four terminal aryl groups and the para-phenyl substituent of 4-phenyl pyridine N-oxide to be in the order of 1 kcal mol(-1) . The complex formation rate was found to be close to the diffusion control suggesting that the free host adopted a 1,3-alternate conformation. Finally, we attempted to gain water solubility of SAE-calix[4]pyrroles using derivatives that display four ionizable or charged groups at their upper rims.

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Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors

Cited by 66 publications

References 38 publications

Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives

Synthetic Receptors for the High‐Affinity Recognition of O‐GlcNAc Derivatives

Platform Synthetic Lectins for Divalent Carbohydrate Recognition in Water

Super Aryl‐Extended Calix[4]pyrroles: Synthesis, Binding Studies, and Attempts To Gain Water Solubility

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