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Incorporation of [2H1]-(1R,2R)- and [2H1]-(1S,2R)-glycerols into the antibiotic nucleocidin in Streptomyces calvus
Organic & Biomolecular Chemistry ( IF 3.2 ) Pub Date : 2017-09-11 00:00:00 , DOI: 10.1039/c7ob02163a
Xuan Feng 1, 2, 3, 4 , Nawaf Al Maharik 1, 2, 3, 4 , Axel Bartholomé 1, 2, 3, 4 , Jeffrey E. Janso 5, 6, 7 , Usa Reilly 5, 6, 7 , David O'Hagan 1, 2, 3, 4
Affiliation  

Deuterium incorporations from [2H1]-(1R,2R) and [2H1]-(1S,2R) glycerols into the fluorine containing antibiotic nucleocidin, in Streptomyces calvus indicate that one deuterium atom is incorporated at the C-5′ site of nucleocidin from each of these isotopomers of glycerol. Two deuteriums become incorporated at C-5′ of nucleocidin after a feeding experiment with [2H5]-glycerol. These observations indicate that there is no obligate oxidation of the pro-R hydroxymethyl group of glycerol as it progresses through the pentose phosphate pathway and becomes incorporated into the fluorinated antibiotic.

中文翻译:

将[ 2 H 1 ]-(1 R,2 R)-和[ 2 H 1 ]-(1 S,2 R)-甘油掺入产犊链霉菌中的抗生素核苷

从[ 2 H 1 ]-(1 R,2 R)和[ 2 H 1 ]-(1 S,2 R)甘油向氟链霉菌亲核素中掺入氘表明,氘原子掺入了一个氘原子。来自甘油的每个这些同位素异构体的核苷亲和素的C-5'位点。在用[ 2 H 5 ]-甘油进行补料实验后,两个氘在核仁亲和素的C-5'处结合。这些观察结果表明pro-R没有专一氧化 甘油的羟甲基通过戊糖磷酸途径发展并掺入氟化抗生素中。
更新日期:2017-09-18
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