[HTML][HTML] Acylation of naturally occurring and synthetic 1-deoxysphinganines by ceramide synthase: formation of N-palmitoyl-aminopentol produces a toxic metabolite …

HU Humpf, EM Schmelz, FI Meredith, H Vesper… - Journal of Biological …, 1998 - ASBMB
Fumonisin B 1 (FB 1) is the predominant member of a family of mycotoxins produced
byFusarium moniliforme (Sheldon) and related fungi. Certain foods also contain the
aminopentol backbone (AP 1) that is formed upon base hydrolysis of the ester-linked
tricarballylic acids of FB 1. Both FB 1 and, to a lesser extent, AP 1 inhibit ceramide synthase
due to structural similarities between fumonisins (as 1-deoxy-analogs of sphinganine) and
sphingoid bases. To explore these structure-function relationships further, erythro-and threo …