鞘氨醇胺的生物合成研究：Stephacidin A 的同位素合成及在鞘氨醇胺 B 和 Sclerotiamide 中的掺入。
Biosynthetic studies of the notoamides: isotopic synthesis of stephacidin A and incorporation into notoamide B and sclerotiamide.
机构信息
Department of Chemistry, Colorado State University, 1301 Center Avenue, Fort Collins, Colorado 80523, USA.
出版信息
Org Lett. 2011 Aug 5;13(15):3802-5. doi: 10.1021/ol201284y. Epub 2011 Jun 30.
Abstract
The advanced natural product stephacidin A is proposed as a biosynthetic precursor to notoamide B in various Aspergillus species. Doubly (13)C-labeled racemic stephacidin A was synthesized and fed to cultures of the terrestrial-derived fungus, Aspergillus versicolor NRRL 35600, and the marine-derived fungus, Aspergillus sp. MF297-2. Analysis of the metabolites revealed enantiospecific incorporation of intact (-)-stephacidin A into (+)-notoamide B in Aspergillus versicolor and (+)-stephacidin A into (-)-notoamide B in Aspergillus sp. MF297-2. (13)C-Labeled sclerotiamide was also isolated from both fungal cultures.
摘要
高级天然产物 Stephacidin A 被提议为各种 Aspergillus 物种中 Notoamide B 的生物合成前体。合成了双（13）C 标记的外消旋 Stephacidin A，并将其饲喂给陆地来源的真菌 Aspergillus versicolor NRRL 35600 和海洋来源的真菌 Aspergillus sp. MF297-2 的培养物。对代谢产物的分析表明，（-）-Stephacidin A 在 Aspergillus versicolor 中以对映体特异性的方式掺入（+）-Notoamide B，而（+）-Stephacidin A 在 Aspergillus sp. MF297-2 中掺入（-）-Notoamide B。（13）C 标记的 Sclerotiamide 也从两种真菌培养物中分离出来。
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