Title: Apoptolidin
CAS Registry Number: 194874-06-1
CAS Name: O-2,6-Dideoxy-3-O-methyl-b-D-arabino-hexopyranosyl-(1®4)-2,6-dideoxy-3-C-methyl-a-L-arabino-hexopyranosyl-(1®8)-3,5,7-trideoxy-1-C-[(2S,4S,5S,8E,10E,12R,13R,14E,16E,18E)-12-[(6-deoxy-4-O-methyl-a-L-glucopyranosyl)oxy]-5-hydroxy-4-methoxy-9,13,15,17,19-pentamethyl-20-oxooxacycloeicosa-8,10,14,16,18-pentaen-2-yl]-3,5-dimethyl-9-O-methyl-L-glycero-a-D-galacto-2-nonulopyranose
Manufacturers' Codes: FU-40A
Molecular Formula: C58H96O21
Molecular Weight: 1129.37
Percent Composition: C 61.68%, H 8.57%, O 29.75%
Literature References: Natural product isolated from Nocardiopsis sp.; specifically induces apoptosis in transformed tumor cells. Isoln, properties and bioactivity: J. W. Kim et al., J. Antibiot. 50, 628 (1997). Structure: Y. Hayakawa et al., J. Am. Chem. Soc. 120, 3524 (1998). Partial synthesis: J. Schuppan et al., Tetrahedron Lett. 41, 621 (2000); K. C. Nicolaou et al., Chem. Commun. 2000, 307. Review of synthetic methods: P. T. Daniel et al., Angew. Chem. Int. Ed. 45, 872-893 (2006).
Properties: Colorless powder, mp 128-130°. [a]21D -5.2° (c = 1.0 in methanol). uv max (methanol): 234, 320 nm (e 28300, 22000).
Melting point: mp 128-130°
Optical Rotation: [a]21D -5.2° (c = 1.0 in methanol)
Absorption maximum: uv max (methanol): 234, 320 nm (e 28300, 22000) |