Mossine Valeri V, Barnes Charles L, Mawhinney Thomas P
Department of Biochemistry, University of Missouri, Columbia, MO 65211, USA.
Carbohydr Res. 2007 Jan 15;342(1):131-8. doi: 10.1016/j.carres.2006.11.011. Epub 2006 Nov 16.
Within a set of food-related Amadori compounds, crystalline N-(1-deoxy-beta-D-fructopyranos-1-yl)-l-histidine monohydrate (Fru-l-HisxH(2)O) has an unusually low solubility in water, which we determined as 0.21 g/100 g at 25 degrees C. The majority of the other fructose-amino acid conjugates have solubilities exceeding 100 g/100 g in water at this temperature. We report the crystal structure data on Fru-l-HisxH(2)O. The conformation of the carbohydrate is the normal (2)C(5) pyranose chair. Bond lengths and valence angles compare well with the average values from a number of pyranose structures. All hydroxyl and carboxyl oxygen atoms, all nitrogen atoms and the water molecule are involved in an extensive hydrogen bonding, which forms a network of infinite chains with small antidromic rings.
在一组与食物相关的阿马多里化合物中，结晶态的N-(1-脱氧-β-D-吡喃果糖基)-L-组氨酸一水合物（Fru-L-His·xH₂O）在水中的溶解度异常低，我们测定其在25℃时为0.21 g/100 g。在此温度下，大多数其他果糖-氨基酸共轭物在水中的溶解度超过100 g/100 g。我们报告了Fru-L-His·xH₂O的晶体结构数据。碳水化合物的构象为正常的(2)C₅吡喃糖椅式。键长和价键角与许多吡喃糖结构的平均值相当。所有的羟基和羧基氧原子、所有的氮原子以及水分子都参与了广泛的氢键作用，形成了带有小反向环的无限链网络。
