ol9b04002_si_001.pdf (11.58 MB)
Formation of Terrestric Acid in Penicillium crustosum Requires Redox-Assisted Decarboxylation and Stereoisomerization
journal contribution
posted on 2019-12-13, 16:34 authored by Jie Fan, Ge Liao, Lena Ludwig-Radtke, Wen-Bing Yin, Shu-Ming LiCrustosic acid (1) differs from terrestric
acid (2) by a 5β-carboxylmethyl at the tetronate
ring instead
of a 5α-methyl group in Penicillium crustosum. The formation of 1 via carboxylcrustic and viridicatic
acid was confirmed by gene deletion and heterologous expression. The
conversion of 1 to 2 requires a decarboxylation-mediated
olefination by TraH and subsequent reduction by TraD. The redox-assisted
decarboxylation and stereoisomerization proved the biosynthetic relationships
of fungal acyltetronates with different stereochemistry.
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Penicillium crustosum Requires Redox-Assisted Decarboxylationheterologous expressionviridicatic acidredox-assisted decarboxylationbiosynthetic relationships5α- methyl groupStereoisomerization Crustosic acidformationgene deletionPenicillium crustosumterrestric acid5β- carboxylmethyltetronate ringdecarboxylation-mediated olefination
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