This article reports the efficient enzymatic synthesis of a homologous series of isomaltulose-derived oligosaccharides with degrees of polymerization ranging from 3 to 9 through the transglucosylation reaction using a dextransucrase from Leuconostoc mesenteroides B-512F. The total oligosaccharide yield obtained under optimal conditions was of 41-42% (in weight respect to the initial amount of isomaltulose) after 24-48 hours of reaction. Nuclear magnetic resonance (NMR) structural characterization indicated that dextransucrase specifically transferred glucose moieties of sucrose to the C-6 of the nonreducing glucose residue of isomaltulose. Likewise, the monitoring of the progress of the content of each individual oligosaccharide indicated that oligosaccharide acceptor products of low molecular weight acted in turn as acceptors for further transglucosylation to yield oligosaccharides of higher degree of polymerization. The produced isomaltulose-derived oligosaccharides can be considered as isomalto-oligosaccharides (IMOs) since they are linked by only α-(1→6) bonds. In addition, having isomaltulose as core structure, these IMO-like structures could possess appealing bioactive properties which could find potential applications as functional food ingredients.