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The catching-by-polymerization (CBP) oligodeoxynucleotide (oligo or ODN) purification method has been demonstrated suitable for large-scale, parallel, and long oligo purification. The authenticity of the oligos has been verifiedviaDNA sequencing, and gene construction and expression. A remaining obstacle to the practical utility of the CBP method is affordable polymerizable tagging phosphoramidites (PTPs) that are needed for the method. In this article, we report scalable synthesis of the four nucleoside (dA, dC, dG and T) precursors to the PTPs using a route having five steps from inexpensive starting materials. The overall yields ranged from 21% to 35%. The scales of the synthesis presented here are up to 2.1 grams of the precursors. Because the syntheses are chromatography-free, further scaling up the syntheses of the precursors have become more feasible. With the precursors, the PTPs can be synthesized in one step using standard methods involving a chromatography purification. 

The targeting of facilitative sugar transporters (GLUTs) has been utilized in the development of tools for diagnostics and therapy. The interest in this area is promoted by the phenomenon of alterations in cellular metabolic processes that are linked to multitudes of metabolic disorders and diseases. However, nonspecific targeting (e.g., glucose-transporting GLUTs) leads to a lack of disease detection efficiency. Among GLUTs, GLUT5 stands out as a prominent target for developing specific molecular tools due to its association with metabolic diseases, including cancer. This work reports a non-radiolabeled fluoride (19F) coumarin-based glycoconjugate of 2,5-anhydro-D-mannitol as a potential PET imaging probe that targets the GLUT5 transporter. Inherent fluorescent properties of the coumarin fluorophore allowed us to establish the probe’s uptake efficiency and GLUT5-specificity in a GLUT5-positive breast cell line using fluorescence detection techniques. The click chemistry approach employed in the design of the probe enables late-stage functionalization, an essential requirement for obtaining the radiolabeled analog of the probe for future in vivo cancer imaging applications. The high affinity of the probe to GLUT5 allowed for the effective uptake in nutrition-rich media.