This diploma thesis is focused on the technology of producing mead from the chosen kind of honey with a variety of sugar concentrations with the use of modern producing technological procedures with the cold and hot process. The theoretical part is focused on the history of mead and its technological development. It focuses, in detail, on modern large scale technologies – both cold and also the hot process. In the practical part of the thesis, the production of samples of mead with various sugar concentrations from three kinds of honey with the use of two technological processes (hot and cold process) was conducted firstly. Secondly, the characteristics of the samples were conducted from the view of the volume of HMF – Hydroxymethylfurfural, ethanol, glucose, fructose, the chosen organic acids and elements with sensory analysis. The prepared samples were compared and discussed concerning differences to find out the differences of the use of the two manufacturing technologies (cold and hot process), the chosen kinds of honey and the influence of sugar before the fermentation on the final product.

Enzymatic oxidation of 5-hydroxymethylfurfural (HMF) and its oxidized derivatives was studied using three fungal enzymes: wild-type aryl alcohol oxidase (AAO) from three fungal species, wild-type peroxygenase from Agrocybe aegerita (AaeUPO), and recombinant galactose oxidase (GAO). The effect of pH on different reaction steps was evaluated and apparent kinetic data (Michaelis-Menten constants, turnover numbers, specific constants) were calculated for different enzyme-substrate ratios and enzyme combinations. Finally, the target product, 2,5-furandicarboxylic acid (FDCA), was prepared in a multi-enzyme cascade reaction combining three fungal oxidoreductases at micro-scale. Furthermore, an oxidase-like reaction is proposed for heme-containing peroxidases, such as UPO, horseradish peroxidase, or catalase, causing the conversion of 5-formyl-2-furancarboxylic acid into FDCA in the absence of exogenous hydrogen peroxide.

Cette thèse est une exploration de l’utilisation d’aldéhydes furaniques biosourcés, tels que l’hydroxyméthyl furfural (HMF) et ses analogues, en tant que substrat pour la réaction de Morita-Baylis-Hillman (MBH). L’étendue de la réaction a été étudiée avec un focus sur la possibilité d’utiliser des milieux aqueux et biosourcés pour effectuer cette transformation. En premier lieu, l’étude a concerné la réaction de MBH du glycosyloxyméthylfurfural (GFM) avec des motifs acryliques, conduisant dans des rendements acceptables à de nouveaux glycodérivés porteurs de motifs α-hydroxyacrylates and α-méthylène-β-amino acrylates. Pour les réactions conduisant aux α-hydroxyacrylates, l’eau peut être utilisée comme solvant, de même que des mélanges d’eau et de diméthylisosorbide (DMI), remplaçant ainsi efficacement le dioxane ou le THF comparativement aux méthodes habituellement employées. Les esters acryliques de départ pouvant être eux-mêmes biosourcés, les glycoacrylates obtenus par la réaction MBH sont donc potentiellement 100% biosourcés. La version aza-MBH de la réaction a été ensuite explorée, associant 3 composants: le GMF, une sulfonamide et un accepteur de Micheal, conduisant à de nouveaux α-méthylène-b-amino carbonyl dérivatives construits sur un motif glucidique. L’étude s’est ensuite focalisée sur le HMF lui-même. Plusieurs solvants biosourcés, en particulier le 2-hydroxymethyl THF et l’isopropylidénéglycerol, se sont révélés efficaces pour la réaction de MBH du HMF avec l’acrylate d’éthyle. Pour le HMF et le furfural, la réaction est améliorée si de l’eau est ajoutée; ce qui permet d’étendre la gamme de solvants biosourcés pouvant être utilisée dans ce processus. Il a aussi été montré que l’imidazolyl alcool bicyclique DPI est un catalyseur très efficace pour la réaction MBH du HMF, du furfural ou du GMF avec des énones cycliques, conduisant à une diversité de nouvelles structures par une voie écorespectueuse et efficacement. / This thesis is an exploration of the use of biosourced furanic aldehydes, namely hydroxymethyl furfural (HMF) and analogues, as a substrate for the Morita-Baylis-Hillman (MBH) reaction. The scope of the reaction has been explored, with a focus on the possibility to perform the reaction in aqueous or biobased medium. First, the MBH reaction of the glucosyloxymethylfurfural (GMF) with acrylic building blocks has been explored, led to two new series of glycoderivatives containing α-hydroxyacrylates and α-methylene-β-amino acrylates in fair yields. For the coupling reaction which produces the α-hydroxyacrylates, water can be used as the solvent. Mixtures of water and dimethylisosorbide (DMI) have also been shown to be possibly used in the reactions, allowing replacement of dioxane or THF compared to previous methods. The strategy is atom-economical. Due to the fact that those acrylic esters are also available from biomass, such kind of glycoacrylates appears as possibly 100% bio-based. The aza-MBH version of the reaction was further explored, studying the reaction involving the three components GMF, sulfonamides and a Micheal acceptor, leading to carbohydrate-based α-methylene-β-amino carbonyl derivatives. The focus was then made on HMF itself. Several biobased solvents, in particular 2-hydroxymethyl THF and isopropylideneglycerol, could be used for the MBH reaction of HMF and ethyl acrylate. For HMF and furfural, the reaction was improved when water was added allowing to widen the range of biobased solvent systems. We have also found that the bicyclic imidazolyl alcohol DPI is an efficient catalyst for the aqueous MBH reaction between HMF, furfural, GMF, and cyclic enones that gives access to a variety of potentially very useful molecules in an efficient and environmentally friendly way.