The Role of Riboflavin in Beer Flavour Instability: EPR studies and the application of flavin binding proteins

Laane, C.; Roo, Guy de; Ban, E.C.D. van den; Sjauw-En-Wa, M.W.; Duyvis, M.G.; Hagen, W.R.; Berkel, Willem J.H. van; Hilhorst, Riet; Schmedding, D. J. M.; Evans, David J.

doi:10.1002/j.2050-0416.1999.tb00031.x

Cited by 14 publications

(14 citation statements)

References 15 publications

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“…Following this approach, we report here on molecularly imprinted polymers (MIPs) that recognize their targets (riboflavin) effectively under such conditions (Figure 1). Careful fine‐tuning of the synthesis conditions with respect to the choice of template and cross‐linking monomer proved critical and resulted in a polymer which strongly and selectively bound riboflavin in water‐rich media similar to those found in common alcoholic beverages 8…”

Section: Methodssupporting

confidence: 92%

“…A pronounced exotherm was observed under these conditions upon each addition, with no apparent binding‐related signals, which implies that the protein denatures under conditions where the imprinted polymer retains its ability to bind the target. Notably, this occurs in a solvent system which resembles that found in common alcoholic beverages 8…”

Section: Methodsmentioning

confidence: 99%

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An Artificial Riboflavin Receptor Prepared by a Template Analogue Imprinting Strategy

et al. 2005

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Molecular imprinting has resulted in a range of robust polymer-based receptors that are being considered for use in a variety of applications based on molecular recognition. [1] The technique entails polymerization of mono-and polyfunctional monomers in the presence of a template, whose subsequent removal leaves sites that can be reoccupied by the template or a closely related compound. These synthetic receptors are distinguished by their robustness and ease of synthesis, but they also have drawbacks, notably their poor water compatibility and, with notable exceptions, [2][3][4][5] the lack of strategies for imprinting water-soluble target molecules. One approach towards overcoming the latter is to use a nonaqueous imprinting protocol, in which lipophilic templates representing a close structural analogue or substructure of the target are employed. [6,7] Here, a solvent/porogen is chosen such that the intrinsically weak monomer-template interactions based, for example, on hydrogen bonding, electrostatics, or charge transfer, are stabilized. Thus, the use of solvents with low polarity and hydrogen bonding strength is generally favored. Although polymers prepared by this route have displayed selective binding of their targets under aqueous conditions, the effects were typically too weak to be of practical value. Following this approach, we report here on molecularly imprinted polymers (MIPs) that recognize their targets (riboflavin) effectively under such conditions ( Figure 1). Careful fine-tuning of the synthesis conditions with respect to the choice of template and cross-linking monomer proved critical and resulted in a polymer which strongly and selectively bound riboflavin in water-rich media similar to those found in common alcoholic beverages. [8] For the design of the polymers, we first turned our attention to the functional monomer. The flavin ring system contains an imide functionality which contains an acceptordonor-acceptor (ADA) array of hydrogen-bonding sites capable of interacting with receptors containing a complimentary DAD array. Representative of such molecules are 2,6-bisamidopyridines, whose ability to bind to imide functionalities has been widely studied.[9] Accordingly, we chose 2,6-bis(acrylamido)pyridine (BAAPy) as our functional monomer (Scheme 1). [10,11] With regards the choice of template, we focused on flavin and riboflavin derivatives having high solubility in typical imprinting solvents, in this case chloroform (Scheme 1), initially attempting to use N(10)-alkylflavins.[12] However, the solubility of these compounds in chloroform was found to be too low (ca. 16 mm for 1 and only ca. 6 mm for 2) for a conventional template/monomer molar ratio to be used. As expected, polymers prepared using these analogues as templates exhibited low imprinting factors and capacities (see below). Riboflavin tetraesters performed better in this regard, their solubility in chloroform being far greater than that of the N(10)-alkylflavins described above (RfAc: 0.2 m, RfPr: 0.6 m, RfBu: 0.8 m). Furthermore...

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Section: Methodssupporting

confidence: 92%

Section: Methodsmentioning

confidence: 99%

An Artificial Riboflavin Receptor Prepared by a Template Analogue Imprinting Strategy

et al. 2005

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“…The effective binding of riboflavin to the apoform of riboflavin‐binding protein has also received biotechnological attention. Aporiboflavin‐binding protein was shown to scavenge riboflavin in model beer solutions, thereby inhibiting the light‐induced formation of reactive oxygen species and sunstruck off‐flavour [148,149].…”

Section: Ion‐exchange Chromatographymentioning

confidence: 99%

Deflavination and reconstitution of flavoproteins

Hefti¹,

Vervoort²,

Berkel³

2003

European Journal of Biochemistry

118

104

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Flavoproteins are ubiquitous redox proteins that are involved in many biological processes. In the majority of flavoproteins, the flavin cofactor is tightly but noncovalently bound. Reversible dissociation of flavoproteins into apoprotein and flavin prosthetic group yields valuable insights in flavoprotein folding, function and mechanism. Replacement of the natural cofactor with artificial flavins has proved to be especially useful for the determination of the solvent accessibility, polarity, reaction stereochemistry and dynamic behaviour of flavoprotein active sites. In this review we summarize the advances made in the field of flavoprotein deflavination and reconstitution. Several sophisticated chromatographic procedures to either deflavinate or reconstitute the flavoprotein on a large scale are discussed. In a subset of flavoproteins, the flavin cofactor is covalently attached to the polypeptide chain. Studies from riboflavindeficient expression systems and site-directed mutagenesis suggest that the flavinylation reaction is a post-translational, rather than a cotranslational, process. These genetic approaches have also provided insight into the mechanism of covalent flavinylation and the rationale for this atypical protein modification.

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“…1998) An alternative strategy toward improving the robustness and quality of beer flavor could be the selective removal of these flavins from the beer. (Laane et al. 1999; Duyvis et al.…”

Section: Introductionmentioning

confidence: 99%

“…(Cladman et al 1998) An alternative strategy toward improving the robustness and quality of beer flavor could be the selective removal of these flavins from the beer. (Laane et al 1999;Duyvis et al 2002) Unfortunately, the use of the natural receptor, riboflavin binding protein (RfBP), for this purpose, is hampered by its poor stability at the slightly acidic pH of beer (pH~4.2). Thus, the food industry, and the brewing industry in particular, could profit from robust receptors with the ability to selectively bind and remove riboflavin from food and beverage matrices, without otherwise affecting the respective product.…”

Section: Introductionmentioning

confidence: 99%

Selective Depletion of Riboflavine From Beer Using Membranes Incorporating Imprinted Polymer Particles

Borrelli¹,

Barsanti²,

Silvestri³

et al. 2011

Journal of Food Processing and Preservation

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The synthesis and characterization of imprinted polymer composite membranes and use of the membranes for depleting riboflavine from beer are hereby reported. The membranes were prepared by phase inversion of a suspension of imprinted polymer particles, which had previously been shown to exhibit selective recognition of vitamin B2 in aqueous media in a solution of poly‐methylmethacrylate and polyethylenglycol in acetone. Membranes with different loads of imprinted particles were prepared and characterized by scanning electron microscopy, Fourier‐transform infrared chemical imaging and permeability measurements. Subsequently they were tested in both static and dynamic partitioning experiments concerning their ability to bind riboflavine versus other competing solutes such as lumichrome and uridine. The membranes exhibited a pronounced selectivity for riboflavine and were capable of partially depleting nearly 80% of the vitamin from beer. Meanwhile, a membrane prepared identically using nonimprinted particles resulted in a maximum removal of nearly 50%, however, with low selectivity. PRACTICAL APPLICATIONS Membranes incorporating molecularly imprinted polymer particles is a new tool for food processing allowing the traceless removal of preselected substances, e.g., flavors, spoilage agents or impurities. As suggested by the results presented in this contribution, such membranes could potentially find use in the brewing industry for selective depletion of riboflavine thus leading to enhanced beer stability.

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The Role of Riboflavin in Beer Flavour Instability: EPR studies and the application of flavin binding proteins

Cited by 14 publications

References 15 publications

An Artificial Riboflavin Receptor Prepared by a Template Analogue Imprinting Strategy

An Artificial Riboflavin Receptor Prepared by a Template Analogue Imprinting Strategy

Deflavination and reconstitution of flavoproteins

Selective Depletion of Riboflavine From Beer Using Membranes Incorporating Imprinted Polymer Particles

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