دورية أكاديمية
Enantioselective synthesis of all stereoisomers of geosmin and of biosynthetically related natural products.
| العنوان: | Enantioselective synthesis of all stereoisomers of geosmin and of biosynthetically related natural products. |
|---|---|
| المؤلفون: | Yin Z; Kekulé-Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany. dickschat@uni-bonn.de., Maczka M; Institute for Organic Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany., Schnakenburg G; Institute for Inorganic Chemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany., Schulz S; Institute for Organic Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany., Dickschat JS; Kekulé-Institute for Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany. dickschat@uni-bonn.de. |
| المصدر: | Organic & biomolecular chemistry [Org Biomol Chem] 2024 Jul 17; Vol. 22 (28), pp. 5748-5758. Date of Electronic Publication: 2024 Jul 17. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101154995 Publication Model: Electronic Cited Medium: Internet ISSN: 1477-0539 (Electronic) Linking ISSN: 14770520 NLM ISO Abbreviation: Org Biomol Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Cambridge, UK : Royal Society of Chemistry, c2003- |
| مواضيع طبية MeSH: | Biological Products*/chemistry , Biological Products*/chemical synthesis , Naphthols*/chemistry , Naphthols*/chemical synthesis , Streptomyces*/chemistry, Stereoisomerism ; Molecular Structure |
| مستخلص: | Synthetic routes to geosmin and its enantiomer are well established, but the enantioselective synthesis of stereoisomers of geosmin is unknown. Here a stereoselective synthesis of all stereoisomers of geosmin is reported, yielding all compounds in high enantiomeric purity. Furthermore, the stereoselective synthesis of a geosmin derivative isolated from a mangrove associated streptomycete was performed, establishing the absolute configuration of the natural product. Finally, a new side product of the geosmin synthase from Streptomyces ambofaciens was isolated and its structure was elucidated by NMR spectroscopy. The absolute configuration of this new compound was determined through a stereoselective synthesis. |
| المشرفين على المادة: | 0 (Biological Products) 0 (Naphthols) MYW912WXJ4 (geosmin) |
| تواريخ الأحداث: | Date Created: 20240626 Date Completed: 20240717 Latest Revision: 20240718 |
| رمز التحديث: | 20240718 |
| DOI: | 10.1039/d4ob00934g |
| PMID: | 38920404 |
| قاعدة البيانات: | MEDLINE |
| تدمد: | 1477-0539 |
|---|---|
| DOI: | 10.1039/d4ob00934g |