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The title compound, alternatively called d-fructose-2-amino-isobutyric acid (FruAib), C 10 H 19 NO 7 , (I), crystallizes exclusively in the β-pyran-ose form, with two conformationally non-equivalent mol-ecules [(I A ) and (I B )] in the asymmetric unit. In solution, FruAib establishes an equilibrium, with 75.6% of the population consisting of β-pyran-ose, 10.4% β-furan-ose, 10.1% α-furan-ose, 3.0% α-pyran-ose and &lt;0.7% the acyclic forms. The carbohydrate ring in (I) has the normal 2  C  5 chair conformation and the amino acid portion is in the zwitterion form. Bond lengths and valence angles compare well with the average values from related pyran-ose structures. All carboxyl, hy-droxy and ammonium groups are involved in hydrogen bonding and form a three-dimensional network of infinite chains that are connected through homodromic rings and short chains. Intra-molecular hydrogen bonds bridge the amino acid and sugar portions in both mol-ecules. A comparative Hirshfeld surfaces analysis of FruAib and four other sugar-amino acids suggests an increasing role of intra-molecular heteroatom inter-actions in crystal structures with an increasing proportion of C-H bonds.

Crystal structure and hydrogen bonding inN-(1-deoxy-β-D-fructopyranos-1-yl)-2-aminoisobutyric acid