For the first time, the X-ray structure of nicotinamide riboside could be determined. Five nicotinamide riboside (NR) derivatives in their native, thioamide and triacetyl protected form could be crystallized as their chloride and bromide salts. The single crystals were obtained with the help of the vapor diffusion technique. The use of the much slower layering technique for crystallization led to the decomposition of the nicotinamide ribosides yielding the corresponding nicotinamide salts. The torsion angles of the five nicotinamide riboside derivatives were compared with those obtained from the two nicotinamide adenine dinucleotide crystal and the three protein nicotinamide riboside cocrystal structures.
NR+ is a highly effective vitamin B3 type supplement due to its unique ability to replenish NAD+ levels. While NR+ chloride is already on the market as a nutritional supplement, its synthesis is challenging, expensive, and low yielding, making it cumbersome for large-scale industrial production. Here we report the novel crystalline NR+ salts, d/l/dl-hydrogen tartrate and d/l/dl-hydrogen malate. Their high-yielding, one-pot manufacture does not require specific equipment and is suitable for multi-ton scale production. These new NR+ salts seem ideal for nutritional applications due to their bio-equivalence compared to the approved NR+ chloride. In addition, the crystal structures of all stereoisomers of NR+ hydrogen tartrate and NR+ hydrogen malate and a comparison to the known NR+ halogenides are presented.
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