127941-81-5Relevant articles and documents
Elucidation of pseurotin biosynthetic pathway points to trans-acting C-methyltransferase: Generation of chemical diversity
Tsunematsu, Yuta,Fukutomi, Manami,Saruwatari, Takayoshi,Noguchi, Hiroshi,Hotta, Kinya,Tang, Yi,Watanabe, Kenji
supporting information, p. 8475 - 8479 (2014/08/18)
Pseurotins comprise a family of structurally related Aspergillal natural products having interesting bioactivity. However, little is known about the biosynthetic steps involved in the formation of their complex chemical features. Systematic deletion of the pseurotin biosynthetic genes in A. fumigatus and invivo and invitro characterization of the tailoring enzymes to determine the biosynthetic intermediates, and the gene products responsible for the formation of each intermediate, are described. Thus, the main biosynthetic steps leading to the formation of pseurotinA from the predominant precursor, azaspirene, were elucidated. The study revealed the combinatorial nature of the biosynthesis of the pseurotin family of compounds and the intermediates. Most interestingly, we report the first identification of an epoxidase C-methyltransferase bifunctional fusion protein PsoF which appears to methylate the nascent polyketide backbone carbon atom in trans. A maze: Pseurotins are a family of structurally related bioactive natural products from Aspergilli. Through genetic and biochemical studies, the biosynthetic pathway for the formation of azaspirene, synerazol, and pseurotin A/D have been elucidated, and reveal the combinatorial nature of their biosyntheses. PsoF was identified as bifunctional epoxidase methyltransferase enzyme, thus providing the first example of a trans-acting polyketide C-methyltransferase.
First asymmetric total synthesis of synerazol, an antifungal antibiotic, and determination of its absolute stereochemistry
Hayashi, Yujiro,Shoji, Mitsuru,Mukaiyama, Takasuke,Gotoh, Hiroaki,Yamaguchi, Shinpei,Nakata, Munetaka,Kakeya, Hideaki,Osada, Hiroyuki
, p. 5643 - 5654 (2007/10/03)
By synthesizing two possible diastereomers, the first asymmetric total synthesis of synerazol, an antifungal antibiotic, has been accomplished, allowing determination of its absolute stereochemistry. A more practical second generation route was also estab
