Solvent Effects in Carbohydrate Binding by Synthetic Receptors: Implications for the Role of Water in Natural Carbohydrate Recognition

Klein, Emmanuel; Ferrand, Yann; Barwell, Nicholas P.; Davis, Anthony P.

doi:10.1002/anie.200704733

Cited by 87 publications

(58 citation statements)

References 41 publications

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“…Considering the proposed mode of binding ( Fig. [22][23] This is also in agreement with the plots shown in Fig. Thus, we replaced the MeOH component of the initial mixture by water.…”

Section: Molecular Recognition In Solutionsupporting

confidence: 76%

Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cages

Faggi

Vicent²,

Luis

et al. 2015

Org. Biomol. Chem.

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Registro de acceso restringido Este recurso no está disponible en acceso abierto por política de la editorial. No obstante, se puede acceder al texto completo desde la Universitat Jaume I o si el usuario cuenta con suscripción. Registre d'accés restringit Aquest recurs no està disponible en accés obert per política de l'editorial. No obstant això, es pot accedir al text complet des de la Universitat Jaume I o si l'usuari compta amb subscripció. Restricted access item This item isn't open access because of publisher's policy. The full--text version is only available from Jaume I University or if the user has a running suscription to the publisher's contents.

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“…Considering the proposed mode of binding ( Fig. [22][23] This is also in agreement with the plots shown in Fig. Thus, we replaced the MeOH component of the initial mixture by water.…”

Section: Molecular Recognition In Solutionsupporting

confidence: 76%

Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cages

Faggi

Vicent²,

Luis

et al. 2015

Org. Biomol. Chem.

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“…20 Zewail and coworkers 21,22 studied in detail the dynamic processes associated with the binding between proteins and hydrophobic ligands using femtosecond-resolved fluorescence spectroscopy. Recently, Davis and co-workers 23,24 suggested a mechanism for solvent-induced carbohydrate recognition consistent with different experimental measurements.…”

Section: Introductionsupporting

confidence: 63%

Restricted dynamics of water around a protein–carbohydrate complex: Computer simulation studies

Jana

Bandyopadhyay

2012

The Journal of Chemical Physics

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Water-mediated protein-carbohydrate interaction is a complex phenomenon responsible for different biological processes in cellular environment. One of the unexplored but important issues in this area is the role played by water during the recognition process and also in controlling the microscopic properties of the complex. In this study, we have carried out atomistic molecular dynamics simulations of a protein-carbohydrate complex formed between the hyaluronan binding domain of the murine Cd44 protein and the octasaccharide hyaluronan in explicit water. Efforts have been made to explore the heterogeneous influence of the complex on the dynamic properties of water present in different regions around it. It is revealed from our analyses that the heterogeneous dynamics of water around the complex are coupled with differential time scales of formation and breaking of hydrogen bonds at the interface. Presence of a highly rigid thin layer of motionally restricted water molecules bridging the protein and the carbohydrate in the common region of the complex has been identified. Such water molecules are expected to play a crucial role in controlling properties of the complex. Importantly, it is demonstrated that the formation of the protein-carbohydrate complex affects the transverse and longitudinal degrees of freedom of the interfacial water molecules in a heterogeneous manner.

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“…With the availability of receptors 51 and 52, this approach could be reduced to practice [105]. Both had been prepared in water soluble form (51c and 52a) and in versions soluble in chloroform (51a and 52b, the latter being the immediate precursor of 52a).…”

Section: Peptide-based Designsmentioning

confidence: 99%

Progress in biomimetic carbohydrate recognition

Walker

Joshi

Davis

2009

Cell. Mol. Life Sci.

109

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The importance of carbohydrate recognition in biology, and the unusual challenges involved, have lead to great interest in mimicking saccharide-binding proteins such as lectins. In this review, we discuss the design of artificial carbohydrate receptors, focusing on those which work under natural (i.e. aqueous) conditions. The problem is intrinsically difficult because of the similarity between substrate (carbohydrate) and solvent (water) and, accordingly, progress has been slow. However, recent developments suggest that solutions can be found. In particular, the "temple" family of carbohydrate receptors show good affinities and excellent selectivities for certain all-equatorial substrates. One example is selective for O-linked beta-N-acetylglucosamine (GlcNAc, as in the O-GlcNAc protein modification), while another is specific for beta-cellobiosyl and closely related disaccharides. Both show roughly millimolar affinities, matching the strength of some lectin-carbohydrate interactions.

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Solvent Effects in Carbohydrate Binding by Synthetic Receptors: Implications for the Role of Water in Natural Carbohydrate Recognition

Cited by 87 publications

References 41 publications

Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cages

Stereoselective recognition of the Ac-Glu-Tyr-OH dipeptide by pseudopeptidic cages

Restricted dynamics of water around a protein–carbohydrate complex: Computer simulation studies

Progress in biomimetic carbohydrate recognition

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