title: Selective substitution of 31/42-OH in rapamycin guided by an in situ IR technique.
abstract: An in situ IR technique was applied in the selective synthesis of the key intermediate for rapamycin derivatives, which made the reaction endpoint easily defined. This technology solved a bothersome problem in the preparation of rapamycin derivatives, and based on this technique, the 31-OH and 42-OH of rapamycin were chemically modified by a series of quaternary ammonium salts to generate 11 compounds. The solubility of all these compounds was remarkably improved (25,000 times higher than that of rapamycin) and their structures were confirmed by MS, IR, 1D and 2D NMR techniques.
authors.affiliation: Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang 110016, China. caoshuangknight@163.com.
authors.forename: Shuang
authors.initials: S
authors.lastname: Cao
authors.affiliation: Laboratory of Computer-Aided Drug Design & Discovery, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. hapwave@163.com.
authors.forename: Xinbo
authors.initials: X
authors.lastname: Zhou
authors.affiliation: Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang 110016, China. yangmarshal88@163.com.
authors.forename: Yuanshuai
authors.initials: Y
authors.lastname: Yang
authors.affiliation: Laboratory of Computer-Aided Drug Design & Discovery, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China. zhongwu@bmi.ac.cn.
authors.forename: Wu
authors.initials: W
authors.lastname: Zhong
authors.affiliation: Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Shenyang 110016, China. suntiemin@126.com.
authors.forename: Tiemin
authors.initials: T
authors.lastname: Sun
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D000644:Quaternary Ammonium Compounds; D020123:Sirolimus / Q000737:chemistry*; D012995:Solubility; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: D000644:Quaternary Ammonium Compounds; D020123:Sirolimus