The saccharide-hydrazide linkage: molecular and crystal structures of the semicarbazide derivatives of D-glucose, D-galactose, and D-xylose, including a 'forbidden' conformation of the galactose derivative
The saccharide-hydrazide linkage: molecular and crystal structures of the semicarbazide derivatives of D-glucose, D-galactose, and D-xylose, including a 'forbidden' conformation of the galactose derivative
复制标题
DOI：
10.1016/s0008-6215(01)00278-6
复制
发表时间：
2002-01-07
影响因子：
3.1
通讯作者：
Ojala, WH
中科院分区：
文献类型：
--
作者：
Ojala, CR;Ostman, JM;Ojala, WH
描述了D-葡萄糖、D-半乳糖和D-木糖的氨基脲衍生物的X-射线晶体结构。M是固态的吡喃葡萄糖基衍生物。葡萄糖氨基脲结晶为二水合物。发现半乳糖氨基脲的两种不同构象，一种具有gg侧链取向，这对于具有C-4（1）-D-半乳糖构型的单糖是不利的。在另外两个已知的例子中，这种构象是通过分子内氢键稳定的，但在目前的结构中，涉及侧链的氢键是分子间的。在这些氨基脲中，N-N-C=O扭转角约为180度，而2-苯甲酰基-1-（α-D-吡喃木糖基）肼的两种固态构象中的扭转角为0.60度和13.9度[Ernholt，B.五、艾森岛B.; Lohse，A.;普莱斯纳岛W的;詹森，K. B.;哈泽尔河G.地;梁某; Jakobsen，A.; Bols，M，Chem. Eur. J. 2000，6，278-287]水分子和羰基氧大量参与H-键合。(C)2002爱思唯尔科技有限公司版权所有。
The X-ray crystal structures of the semicarbazide derivatives of D-glucose, D-galactose, and D-xylose are described. M are glycopyranosyl derivatives in the solid state. The glucose semicarbazide crystallizes as a dihydrate. Two different conformations of the galactose semicarbazide are found, one having the gg side-chain orientation unfavorable for monosaccharides having the C-4(1)-D-galacto configuration. In the two other known examples, this conformation is stabilized by an intramolecular hydrogen bond, but in the current structure, the hydrogen bonds involving the side chain are intermolecular. In these semicarbazides the N-N-C=O torsional angle is approximately 180degrees, in contrast to the angles of 0.60 and 13.9degrees in the two solid-state conformations of 2-benzoyl-1-(alpha-D-xylopyranosyl)hydrazine [Ernholt, B. V.; Thomsen, I. B.; Lohse, A.; Plesner, I. W.; Jensen, K. B.; Hazell, R. G.; Liang, X.; Jakobsen, A.; Bols, M, Chem. Eur. J. 2000, 6, 278-287] The water molecules and the carbonyl oxygen are heavily involved in H-bonding. (C) 2002 Elsevier Science Ltd. All rights reserved.