UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR 7201), FR 2769, C181, 4 place Jussieu, 75005 Paris, France.
Carbohydr Res. 2012 Nov 1;361:219-24. doi: 10.1016/j.carres.2012.07.005. Epub 2012 Jul 16.
The synthesis of three conformationally locked d-glucopyranoside analogs displaying the hydroxyl pattern of the parent sugar is described. A two carbon bridge connecting the C-2 and C-5 atoms of the pyranose ring allows a torsion of the sugar ring toward a (2,5)B conformation as confirmed by conformational analysis. This conformation is strongly believed to be adopted by the oxacarbenium ion-like transition state of several inverting glucosidases.
描述了三种构象锁定的 d-吡喃葡萄糖苷类似物的合成，这些类似物显示出母体糖的羟基模式。一个连接吡喃糖环的 C-2 和 C-5 原子的两个碳原子桥允许糖环向（2,5）B 构象扭转，这一点通过构象分析得到了证实。这种构象被认为是几种反转糖苷酶的氧碳鎓离子样过渡态所采用的。
