Sugar has gained somewhat of a bad reputation because of its contribution to obesitas and related diseases. Although other carbohydrates can offer health benefits with respect to cariogenic, caloric and prebiotic profile, very few have been systematically evaluated as alternative for classical table sugar. In this project, two analogues of sucrose will be explored in which the fructose moiety is replaced by either allulose (3-epimer) or tagatose (4-epimer). The corresponding monosaccharides have already been approved as low-caloric sweeteners for human consumption but will now be incorporated in a non-reducing disaccharide to mimic the properties of sucrose as closely as possible. To that end, new synthetic enzymes will be designed, and cost-effective production processes will be developed. Finally, human (small intestine) and microbial (mouth and large intestine) digestion of these sucrose analogues will be examined to establish structure-function relationships with respect to their fate in the digestive tract. If successful, taste panels will also be recruited to evaluate their sensory perception (taste and texture) in various food formulations. As such, this project will contribute significantly to our fundamental knowledge of this field while its applied potential towards the development of healthier food products is also evident.