Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of heat stable antifungal factor (HSAF)

Olson Andrew S.; Chen Haotong; Du Liangcheng; Dussault Patrick H.

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Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of heat stable antifungal factor (HSAF)

机译：合成2,4,6,8,10-十二烷酸甲酸硫酯作为热稳定抗真菌因子（HSAF）生物合成的基材

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The N-acetylcystamine (SNAC) thioester of dodecapentaenoic acid, an analog of a putative intermediate in the biosynthesis of Heat Stable Antifungal Factor (HSAF), is synthesized. Key steps include sequential Horner-Emmons homologations with the Weinreb amide of diethylphosponoacetic acid, and thioesterification of an aldol-derived 3-hydroxyalkanoate, which serves as a stable precursor of the sensitive polyenoate. The thioester was investigated as a biosynthetic substrate using a purified nonribosomal peptide synthetase and was not incorporated in the observed products.

机译：合成了十二烷苯甲酸的N-乙酰胞嘧啶（SNAC）硫酯，其在热稳定抗真菌因子（HSAF）生物合成中的推定中间体的类似物。关键步骤包括与脱乙基戊乙酸的Weinreb酰胺的序贯角互象的同源，以及醛醇衍生的3-羟基烷烃的硫酯化，其用作敏感聚环的稳定前体。使用纯化的非纤维素肽合成酶作为生物合成底物研究硫酯，并未掺入观察到的产物中。

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《RSC Advances》 |2015年第15期|共5页
作者
Olson Andrew S.; Chen Haotong; Du Liangcheng; Dussault Patrick H.;
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Univ Nebraska Dept Chem Lincoln NE 68588 USA;

Univ Nebraska Dept Chem Lincoln NE 68588 USA;

Univ Nebraska Dept Chem Lincoln NE 68588 USA;

Univ Nebraska Dept Chem Lincoln NE 68588 USA;

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1. Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of heat stable antifungal factor (HSAF) [J] . Olson Andrew S., Chen Haotong, Du Liangcheng, RSC Advances . 2015,第15期

机译：合成2,4,6,8,10-十二烷酸甲酸硫酯作为热稳定抗真菌因子（HSAF）生物合成的基材
2. Identification of a small molecule signaling factor that regulates the biosynthesis of the antifungal polycyclic tetramate macrolactam HSAF in Lysobacter enzymogenes [J] . Han Yong, Wang Yan, Tombosa Simon, Applied Microbiology and Biotechnology . 2015,第2期

机译：鉴定调节溶菌酶基因中抗真菌多环四酸酯大内酰胺HSAF的生物合成的小分子信号传导因子
3. Biosynthesis of the Polycyclic System in the Antifungal HSAF and Analogues from Lysobacter enzymogenes [J] . Li Yaoyao, Wang Haoxin, Liu Yan, Angewandte Chemie . 2018,第21期

机译：抗真菌HSAF中多环体系的生物合成及来自溶血菌酶的类似物
4. SYNTHESIS AND ANTIFUNGAL ACTIVITY EVALUATION OF NEW BENZIMIDAZOLE-TRIAZOLE DERIVATIVES AS POTENTIAL ERGESTEROL BIOSYNTHESIS INHIBITORS USING LC-MS/MS [C] . Nafiz Oncu Can, Ulviye Acar Cevik, Begum Nurpelin Saglik, International Mass Spectrometry Conference . 2018

机译：新型苯并咪唑 - 三唑衍生物作为使用LC-MS / MS的潜在伊代甲生物合成抑制剂的合成与抗真菌活性评价
5. INHIBITION OF BIOSYNTHESIS OF AFLATOXIN BY CURRENTLY USED AND POTENTIAL ANTIFUNGAL FOOD ADDITIVES (KINETICS, SORBIC ACID, NISIN, NYSTATIN, BHA) [D] . YOUSEF, AHMED ELMELEIGY. 1984

机译：当前和潜在的抗真菌食品添加剂（动力学，山梨酸，日新，NYSTATIN，BHA）对黄曲霉毒素生物合成的抑制作用
6. Synthesis of a 246810-dodecapentanoic acid thioester as a substrate for biosynthesis of Heat Stable Antifungal Factor (HSAF) [O] . Andrew S. Olson, Haotong Chen, Liangcheng Du, -1

机译：246810-十二碳烯酸硫酯的合成作为热稳定抗真菌因子（HSAF）生物合成的底物
7. Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of heat stable antifungal factor (HSAF) [O] . Olson, Andrew S., Chen, Haotong, Du, Liangcheng, 2015

机译：2,4,6,8,10-十二烷酸的合成硫酯作为生物合成热的基质稳定的抗真菌因子（HsaF）

Synthesis of a 2,4,6,8,10-dodecapentanoic acid thioester as a substrate for biosynthesis of heat stable antifungal factor (HSAF)

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