Research Article: 41-Azido-41-de­oxy­rapamycin

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Lijun Xie, Jie Huang, Jian Zuo, Hui Yu, Yuanrong Cheng.


The title compound, C51H78N4O12, is a derivative of rapamycin, a triene macrolide anti­biotic mol­ecule isolated from Streptomyces hygroscopicus. The macrocyclic ring structure has 15 chiral centres, with one of the substituent hy­droxy groups giving an intra­molecular hydrogen bond to a ketone O-atom acceptor. The mol­ecules also form inter­molecular hy­droxy–ketone O—H⋯O hydrogen-bonding associations, giving one-dimensional chains extending along (010). The crystal has 108 Å3 solvent-accessible voids.

Partial Text

For general background on rapamycin, as an immunosuppressant drug for rejection prevention in organ transplantation, see: Calne et al. (1989 ▶). For the anti­cancer properties of rapamycin derivatives, see: Chan (2004 ▶); Sun et al. (2005 ▶); Ayral-Kaloustian et al. (2010 ▶). For the structure of rapamycin, see: White & Swindells (1981 ▶); Findlay & Radics (1980 ▶). For related literature, see: Flack (1983 ▶).