کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5271567 1385442 2013 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Enzymatic syntheses of unnatural head-to-tail pentacyclic triterpenes by tetraprenyl-β-curcumene cyclase
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Enzymatic syntheses of unnatural head-to-tail pentacyclic triterpenes by tetraprenyl-β-curcumene cyclase
چکیده انگلیسی

Little is known of the biosynthesis of sesquarterpenes and the synthesis of unnatural terpenoids by sesquarterpene biosynthetic enzymes has not yet been reported. In this study, the enzymatic cyclization of head-to-tail acyclic triterpene β-hexaprene-a natural product isolated from Bacillus clausii-using tetraprenyl-β-curcumene cyclase (TC) from Bacillus subtilis resulted in the formation of two unnatural pentacyclic triterpenes. It was revealed that B. subtilis TC, which forms tetracyclic terpenoid scaffold from tetraprenyl-β-curcumene in vivo, could be used to construct the 6/6/6/6/6-fused pentacyclic scaffold in vitro, suggesting that the active site cavity of TC has sufficient space to accommodate this unnatural pentacyclic scaffold. This is the first report demonstrating the utility of a sesquarterpene cyclase toward the synthesis of unnatural terpenoids.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 54, Issue 49, 4 December 2013, Pages 6747-6750
نویسندگان
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