Convenient alternative synthesis of the <i>Malassezia</i>-derived virulence factor malassezione and related compounds.

ABSTRACT: Lipophilic yeasts of the genus Malassezia are commensal fungi that constitute the normal skin microbiota but may become pathogenic. These fungi, especially M. furfur, convert tryptophan into various alkaloid indoles such as malassezione, which may serve as virulence factors. To facilitate testing of malassezione as an aryl hydrocarbon receptor agonist and potential glucokinase activator, we developed a convenient synthetic route from commercially available indole-3-acetic acid. Treatment of the N-Boc-protected indole-3-acetic acid with N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) in the presence of DMAP generates the N,N'-Boc-protected malassezione, which upon deprotection yields malassezione in an overall yield of ca. 20%. This is a

SUBMITTER: Ramesh K 

PROVIDER: S-EPMC12415918 | biostudies-literature | 2025

REPOSITORIES: biostudies-literature