Mediation of metal chelation in cysteine-derived tetramate systems

Genome mining and gene deletion experiments in Penicillium crustosum proved the involvement of the PKS-NRPS PemA and the trans-enoyl reductase PemB in the formation of three enantiomeric clavatol-containing tetramate pairs. Overexpression of a transcription factor significantly improved the product yields. Feeding experiments provided evidence for their formation via 1,4-Michael addition of hydroxyclavatol to two tetramates from the Pem pathway. This study provides another example of the involvement of reactive intermediates in multiple biosynthetic pathways.

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Stereoselective Synthesis of β-Thiolated Aryl Amino Acids

Zheng

Yin

Wang

et al. 2022

Synthesis

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A variety of β-thiolated aryl amino acids were readily synthesized with moderate to excellent yields from a readily-accessible thiazoline precursor via 1,4-addition, which can be prepared from cysteine methyl ester hydrochloride in just three steps. The thiolated products can be subsequently deprotected within one single step with high yield and used directly for subsequent solid-phase peptide synthesis.

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Mediation of metal chelation in cysteine-derived tetramate systems

Abstract: A study of bicyclic tetramates modified with a bulky ester, which leads to steric hindrance of distal chelating atoms, is used as a route for the alteration of metal binding ability.

Cited by 4 publications

References 79 publications

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Biosynthesis of Tetramate Derivatives in Penicillium crustosum Reveals the Involvement of ortho-Quinone Methide in Crosstalk of Multiple Pathways

Stereoselective Synthesis of β-Thiolated Aryl Amino Acids

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