8745. Sphingofungins

Description and references

Family of six antifungal agents, sphingofungins A-F, isolated from Aspergillus fumigatus of which sphingofungin C is the most abundant. Specific inhibitors of serine palmitoyltransferase. Isoln and charaterization of sphingofungins A-D: F. VanMiddlesworth et al., J. Antibiot. 45, 861 (1992); of sphingofungins E-F: W. S. Horn et al., ibid. 1692. Stereochemistry of A-D: F. VanMiddlesworth et al., Tetrahedron Lett. 33, 297 (1992). Mechanism of action: M. M. Zweerink et al., J. Biol. Chem. 267, 25032 (1992). Synthesis of D: K. Mori, K. Otaka, Tetrahedron Lett. 35, 9207 (1994); and stereochemistry of E: B. Wang et al., Synlett 2001, S1 904.

Chemical structure

Derivative

Sphingofungin C.

Nomenclature

CAS number: 121025-46-5
5-(Acetyloxy)-2-amino-3,4,14-trihydroxy-6-eicosenoic acid.
C22H41NO7; mol wt 431.56.
C 61.23%, H 9.58%, N 3.25%, O 25.95%.

Properties

Cream colored solid.