Linhardt R J, Baenziger N C, Ronsen B
Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Iowa, Iowa City 52242.
J Pharm Sci. 1990 Feb;79(2):158-62. doi: 10.1002/jps.2600790216.
Amiprilose hydrochloride is a carbohydrate-derived, novel anti-inflammatory with potential application in the treatment of rheumatoid arthritis. A spectroscopy-based approach was undertaken to assign both the relative and absolute configuration of its five chiral centers. The fully assigned 13C and 1H NMR spectra of amiprilose hydrochloride was used to establish the relative stereochemistry of four of its five chiral centers held rigid in its furanose ring system. Parallel synthesis of the enantiomer of amiprilose hydrochloride from L-glucose was followed by CD spectropolarimetry to establish that no inversion of chiral centers had occurred in the synthesis. The hydrobromide salt of amiprilose and its enantiomer were prepared and, together with amiprilose hydrochloride, were crystallized. X-ray crystallographic analysis resulted in the assignment of the absolute configuration of all five chiral centers.
盐酸阿米普明是一种源自碳水化合物的新型抗炎药，在类风湿性关节炎治疗中具有潜在应用价值。采用基于光谱学的方法来确定其五个手性中心的相对构型和绝对构型。盐酸阿米普明的全归属13C和1H NMR光谱用于确定其在呋喃糖环系统中保持刚性的五个手性中心中的四个的相对立体化学。由L-葡萄糖平行合成盐酸阿米普明的对映体，然后进行圆二色光谱偏振法，以确定在合成过程中手性中心没有发生反转。制备了阿米普明的氢溴酸盐及其对映体，并与盐酸阿米普明一起结晶。X射线晶体学分析确定了所有五个手性中心的绝对构型。
