Sphingofungins F and F: Novel serinepalmitoyl transferase inhibitors from Paecilomyces variotii.

Biochemistry, cell biology and molecular biology of lipids ofSaccharomyces cerevisiae

“…Other sphingolipid metabolites, such as ceramides or long-chain base phosphates and the sphingolipids containing inositol, are not taken up by cells and this property has prevented many potentially interesting experiments from being performed. SPT is the target of several potent natural inhibitors, including sphingofungins, 99,310 lipoxamycin, 153 myriocin 175 and viridofungins. 154 In the second step in sphingolipid synthesis, 3-ketodihydrosphingosine is reduced in a reaction utilizing NADPH 204 to produce the long-chain base dihydrosphingosine (sphinganine).…”

Arthrinic Acid, a Novel Antifungal Polyhydroxyacid from Arthrinium phaeospermum

“…This structure, with a highly hydroxylated acid end and a more aliphatic "tail", is very similar to phomenoic acid [1,2]. This kind of lipid-mimic structure is also seen in other bioactive microbial metabolites such a khafrefungin [3] and the sphingofungins [4].…”

The First Total Synthesis of Sphingofungin E and the Determination of its Stereochemistry

“…1 They showed significant biological activity in inhibiting serine palmitoyltransferase, and had antifungal activity against several human pathogenic fungi. 1 They also bear structural resemblance to myriocin (3), 2 a compound 10-100 times more potent than immunosuppressant cyclosporin A.…”

“…1 They showed significant biological activity in inhibiting serine palmitoyltransferase, and had antifungal activity against several human pathogenic fungi. 1 They also bear structural resemblance to myriocin (3), 2 a compound 10-100 times more potent than immunosuppressant cyclosporin A. 3 Although there has been a number of works on the total synthesis and the absolute stereochemistry of 2, 4 the most highly oxygenated member of the family, sphingofungin E, remained untackled, and its stereochemistry was only tentatively assigned.…”

“…3 Although there has been a number of works on the total synthesis and the absolute stereochemistry of 2, 4 the most highly oxygenated member of the family, sphingofungin E, remained untackled, and its stereochemistry was only tentatively assigned. 1 As it is our continued interest in the synthesis of polyhydroxylamines and a-substituted amino acids, we have undertaken the syntheses of both 1 and 2. 5 Herein we report the first total synthesis of sphingofungin E and the determination of its stereochemistry.…”