Talauxins: Hybrid Phenalenone Dimers from Talaromyces stipitatus.,Journal of Natural Products

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Talauxins: Hybrid Phenalenone Dimers from Talaromyces stipitatus.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-03-02 , DOI: 10.1021/acs.jnatprod.9b01066
Nirmal K Chaudhary ₁ , Andrew Crombie ₂ , Daniel Vuong ₂ , Ernest Lacey _{1,

2} , Andrew M Piggott ₁ , Peter Karuso ₁

Affiliation

Cultivation and extraction of the fungus Talaromyces stipitatus led to the isolation of five new oxyphenalenone-amino acid hybrids, which were named talauxins E, Q, V, L, and I based on the corresponding one-letter amino acid codes, along with their putative biosynthetic precursor, duclauxin. The rapid reaction of duclauxin with amino acids to produce talauxins was demonstrated in vitro and exploited to generate a small library of natural and unnatural talauxins. Talauxin V was shown to undergo spontaneous elimination of methyl acetate to yield the corresponding neoclauxin scaffold. This process was modeled using density functional theory calculations, revealing a dramatic change in conformation resulting from the syn elimination of methyl acetate.

中文翻译：

Talauxins：来自Talaromyces stipitatus的杂酚醛酮二聚体。

栽培和提取真菌塔拉木霉（Talaromyces stipitatus）导致分离出五个新的氧苯丙烯酮-氨基酸杂种，根据相应的一个字母的氨基酸代码及其推定名称将其命名为talauxins E，Q，V，L和I生物合成前体duclauxin。在体外证明了duclauxin与氨基酸的快速反应以产生他洛辛，并被利用来生成天然和非天然他洛辛的小文库。已显示Talauxin V自发消除了乙酸甲酯，生成了相应的新clauxin支架。使用密度泛函理论计算对该过程进行建模，揭示了由于乙酸甲酯的同位消除而导致的构象的巨大变化。

更新日期：2020-03-02

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