Remarkably selective saccharide recognition by solid-supported peptide boronic acids

Duggan, Peter J.; Offermann, Daniel A.

doi:10.1016/j.tet.2008.10.095

Cited by 34 publications

(29 citation statements)

References 38 publications

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“…The complete extraction of cellobiose in 100% IL is also encouraging. Furthermore, there is the possibility that boronic acid membrane-based systems could be applied to pretreated biomass in future processing applications [7][8][9]25]. These results demonstrate the potential of this approach to develop an IL pretreatment process technology with high overall sugar yields.…”

Section: Resultsmentioning

confidence: 76%

Recovery of Sugars from Ionic Liquid Biomass Liquor by Solvent Extraction

et al. 2010

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The dissolution of biomass into ionic liquids (ILs) has been shown to be a promising alternative biomass pretreatment technology, facilitating faster breakdown of cellulose through the disruption of lignin and the decrystallization of cellulose. Both biological and chemical catalysis have been employed to enhance the conversion of IL-treated biomass polysaccharides into monomeric sugars. However, biomass-dissolving ILs, sugar monomers, and smaller carbohydrate oligomers are all soluble in water. This reduces the overall sugar content in the recovered solid biomass and complicates the recovery and recycle of the IL. Nearcomplete recovery of the IL and the holocellulose is essential for an IL-based pretreatment technology to be economically feasible. To address this, a solvent extraction technique, based on the chemical affinity of boronates such as phenylboronic acid and naphthalene-2-boronic acid for sugars, was applied to the extraction of glucose, xylose, and cellobiose from aqueous mixtures of 1-ethyl-3-methylimidazolium acetate. It was shown that boronate complexes could extract up to 90% of mono-and disaccharides from aqueous IL solutions, 100% IL systems, and hydrolysates of corn stover containing IL. The use of boronate complexes shows significant potential as a way to recover sugars at several stages in ionic liquid biomass pretreatment processes, delivering a concentrated solution of fermentable sugars, minimizing toxic byproducts, and facilitating ionic liquid cleanup and recycle.

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Section: Resultsmentioning

confidence: 76%

Recovery of Sugars from Ionic Liquid Biomass Liquor by Solvent Extraction

et al. 2010

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“…Therefore, the term boronolectin was coined to refer to this class of sensors/binders [15]. Along this line, there have been extensive efforts in the design and synthesis of boronic acids that change spectroscopic properties upon binding [8,15] and the development of combinatorial methods for the rapid search of peptide/protein-based boronolectins (PBLs) [53,56,[61][62][63] and nucleic-acidbased boronolectins (NBLs) [57]. Recently, the Schultz laboratory has successfully incorporated a boronic-acidmodified amino acid (phenylalanine) into protein for the selection of lectins with enhanced affinities for carbohydrates [64,65].…”

Section: Boronic-acid-based Chemosensorsmentioning

confidence: 99%

“…There are successful examples in all three areas in the development of boronolectin/chemosensor by using boronic acid as a key recognition moiety. Briefly, de novo design has been used for the successful construction of chemosensors for glucose [107] and dopamine [108]; template-directed synthesis has been used for the construction of sensors for fructose as a model [109,110]; and combinatorial libraries have been constructed in search of PBLs [53,56,[61][62][63][64][65] for carbohydrates and NBL glycoproteins [57] and carbohydrates [61,106]. Since computer-based de novo design is discussed in Chapter 5, template-directed sensor synthesis in Chapter 7, and combinatorial approaches to sensor development in Chapter 6, such issues are not discussed further in this chapter.…”

Section: Boronic-acid-based Chemosensorsmentioning

confidence: 99%

Covalent Interactions in Chemosensor Design

2011

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“…A biological example of conformational change induced by a compound containing a vicinal diol can be found in the purinergic receptor family of membrane-bound signalling proteins, which are activated primarily by the purine nucleoside adenosine 47,48 . Because the 2 ′ and 3 ′ hydroxyl groups of ribonucleosides can form stable cyclic boronates [49][50][51][52] , we explored the possibility that ribonucleosides might also be competent ligands for our own receptor mimic. Mixing receptor 4 with 2.0 equiv.…”

mentioning

confidence: 99%

End-to-end conformational communication through a synthetic purinergic receptor by ligand-induced helicity switching

et al. 2013

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The long-range communication of information, exemplified by signal transduction through membrane-bound receptors, is a central biochemical function. Reversible binding of a messenger ligand induces a local conformational change that is relayed through the receptor, inducing a chemical effect typically several nanometres from the binding site. We report a synthetic receptor mimic that transmits structural information from a boron-based ligand binding site to a spectroscopic reporter located more than 2 nm away. Reversible binding of a diol ligand to the N-terminal binding site induces a screw-sense preference in a helical oligo(aminoisobutyric acid) foldamer, which is relayed to a reporter group at the remote C-terminus, communicating information about the structure and stereochemistry of the ligand. The reversible nature of boronate esterification was exploited to switch the receptor sequentially between left- and right-handed helices, while the exquisite conformational sensitivity of the helical relay allowed the reporter to differentiate even between purine and pyrimidine nucleosides as ligands.

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Remarkably selective saccharide recognition by solid-supported peptide boronic acids

Cited by 34 publications

References 38 publications

Recovery of Sugars from Ionic Liquid Biomass Liquor by Solvent Extraction

Recovery of Sugars from Ionic Liquid Biomass Liquor by Solvent Extraction

Covalent Interactions in Chemosensor Design

End-to-end conformational communication through a synthetic purinergic receptor by ligand-induced helicity switching

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