FK228 from Burkholderia thailandensis MSMB43

Abstract

FK228 [systematic name: (1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone], C24H36N4O6S2, also known as FR901228, depsipeptide, NSC 630176, romidepsin, and marketed as Istodax by Celgene Corporation, is crystallized from ethyl acetate in P21 as compared to the absolute configuration of FK228, first crystallized from methanol in P212121 [Shigematsu et al. (1994). J. Antibiot. 47, 311–314]. A slight difference is observed between the absolute configuration of FK228 and the present structure. The molecular structure is stabilized by intramolecular N—H...O hydrogen bonds. In the crystal, molecules are linked via N—H...O hydrogen bonds.