Rajsekhar Gudneppanavar, Rao Chebrolu P, Saarenketo Pauli K, Kolehmainen Erkki, Rissanen Kari
Bioinorganic Laboratory, Department of Chemistry, Indian Institute of Technology, Bombay, 400 076, Mumbai, India.
Carbohydr Res. 2002 Feb 11;337(3):187-94. doi: 10.1016/s0008-6215(01)00311-1.
A total of nine glycosylamines of 4,6-O-butylidene-alpha-D-glucopyranose were synthesized using primary amines having various groups in their ortho- or para-positions. Among these, six are monoglycosylamines, including one primary glycosylamine, and three are bis-glycosylamines. All these compounds were characterized by 1H, 1H-1H COSY, 1H-13C COSY and 13C NMR spectroscopy and FTIR spectra. The FAB mass spectra provided the molecular weights of the products by exhibiting the corresponding molecular ion peaks. The crystal structure of 4,6-O-butylidene-N-(o-chlorophenyl)-beta-D-glucopyranosylamine revealed the C-1 glycosylation, the beta-anomeric nature, and the 4C1 chair conformation of the saccharide unit in the product. In the lattice two types of dimers exist. While one type of dimer is formed through O-H...O type of interactions, the other type is formed via C-H...O type of interactions. In the direction of these C-H...O type of interactions, the dimeric units are connected to form a chain.
使用在邻位或对位带有不同基团的伯胺合成了总共九种4,6-O-亚丁基-α-D-吡喃葡萄糖的糖基胺。其中，六种是单糖基胺，包括一种伯糖基胺，三种是双糖基胺。所有这些化合物都通过1H、1H-1H COSY、1H-13C COSY和13C NMR光谱以及FTIR光谱进行了表征。FAB质谱通过显示相应的分子离子峰提供了产物的分子量。4,6-O-亚丁基-N-(邻氯苯基)-β-D-吡喃葡萄糖胺的晶体结构揭示了产物中糖单元的C-1糖基化、β-端基异构性质和4C1椅式构象。在晶格中存在两种类型的二聚体。一种类型的二聚体通过O-H...O型相互作用形成，另一种类型通过C-H...O型相互作用形成。在这些C-H...O型相互作用的方向上，二聚单元连接形成一条链。
