Abstract
The title compound, alternatively called d-fructose-2-amino-isobutyric acid (FruAib), C10H19NO7, (I), crystallizes exclusively in the β-pyran-ose form, with two conformationally non-equivalent mol-ecules [(IA) and (IB)] 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 <0.7% the acyclic forms. The carbohydrate ring in (I) has the normal 2C5 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.
Highlights
The title compound, alternatively called d-fructose-2-aminoisobutyric acid (FruAib), C10H19NO7, (I), crystallizes exclusively in the -pyranose form, with two conformationally non-equivalent molecules [(IA) and (IB)] in the asymmetric unit
Hydroxy 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
Synthetic fructosamine derivatives have been offered as lectin blockers and antioxidants that might stimulate immune system (Tarnawski, Kulis-Orzechowska & Szelepin, 2007), be potentially useful in prevention of cancer metastasis (Mossine et al, 2010), or neuroinflammation (Song et al, 2016)
Summary
Crystalline FruAib has two conformationally nonequivalent molecules, (IA) and (IB), in the asymmetric unit. The molecules may be considered as conjugates of a carbohydrate, 1-amino-1-deoxy-d-fructose, and an amino acid, 2-aminoisobutyric acid, which are joined through the common amino group. Drate portions in both (IA) and (IB) exist in the 2C5 chair conformation, with puckering parameters Q = 0.582 A , q = 177.7, and f = 224 for (IA) and Q =0.565 A , q = 175.5, and f = 268 for (IB). These parameters correspond to a conformation with the lowest energy possible for fructose
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