The promiscuity of LlNDT-2-catalysed transglycosylations using non-natural nucleobases has been demonstrated using either 2ʹ-deoxycytidine (8) or thymidine as the corresponding 2'deoxyribosyl donor. Structural analysis of LlNDT-2 provided insight into the determinants of acceptor specificity by LlNDT, and thus the generally lower conversion to pyrimidine 2ʹdeoxyribonucleosides compared with purine analogues using equivalent stoichiometry. These transglycosylation reactions are inherently scalable, thus providing an alternative to the use of NPs, which can suffer from the need to prepare a pentose-1-phosphate (6) to drive the equilibrium to completion. This work highlights a workflow to prepare a wider range of nucleoside analogues with sugar modifications typically found in, for example, therapeutic oligonucleotides and nucleoside drugs. Future work will explore the potential to use engineered LlNDT-2 enzymes to enhance substrate scope for acceptors with modifications at the 2′-position and the subsequent potential to prepare nucleosides on scale.