دورية أكاديمية
Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners.
| العنوان: | Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners. |
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| المؤلفون: | Mukai K; Department of Chemistry, University of California, Berkeley, California 94720, USA., de Sant'Ana DP; Department of Chemistry, University of California, Berkeley, California 94720, USA., Hirooka Y; Department of Chemistry, University of California, Berkeley, California 94720, USA., Mercado-Marin EV; Department of Chemistry, University of California, Berkeley, California 94720, USA., Stephens DE; Department of Chemistry, University of California, Berkeley, California 94720, USA., Kou KGM; Department of Chemistry, University of California, Berkeley, California 94720, USA., Richter SC; Department of Chemistry, University of California, Berkeley, California 94720, USA., Kelley N; Department of Chemistry, University of California, Berkeley, California 94720, USA., Sarpong R; Department of Chemistry, University of California, Berkeley, California 94720, USA. |
| المصدر: | Nature chemistry [Nat Chem] 2018 Jan; Vol. 10 (1), pp. 38-44. Date of Electronic Publication: 2017 Sep 18. |
| نوع المنشور: | Journal Article; Research Support, N.I.H., Extramural |
| اللغة: | English |
| بيانات الدورية: | Publisher: Nature Pub. Group Country of Publication: England NLM ID: 101499734 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1755-4349 (Electronic) Linking ISSN: 17554330 NLM ISO Abbreviation: Nat Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: London : Nature Pub. Group |
| مواضيع طبية MeSH: | Dimerization*, Biological Products/*chemical synthesis , Indole Alkaloids/*chemical synthesis , Indole Alkaloids/*chemistry, Biological Products/chemistry ; Molecular Conformation ; Stereoisomerism |
| مستخلص: | Stephacidin A and its congeners are a collection of secondary metabolites that possess intriguing structural motifs. They stem from unusual biosynthetic sequences that lead to the incorporation of a prenyl or reverse-prenyl group into a bicyclo[2.2.2]diazaoctane framework, a chromene unit or the vestige thereof. To complement biosynthetic studies, which normally play a significant role in unveiling the biosynthetic pathways of natural products, here we demonstrate that chemical synthesis can provide important insights into biosynthesis. We identify a short total synthesis of congeners in the reverse-prenylated indole alkaloid family related to stephacidin A by taking advantage of a direct indole C6 halogenation of the related ketopremalbrancheamide. This novel strategic approach has now made possible the syntheses of several natural products, including malbrancheamides B and C, notoamides F, I and R, aspergamide B, and waikialoid A, which is a heterodimer of avrainvillamide and aspergamide B. Our approach to the preparation of these prenylated and reverse-prenylated indole alkaloids is bioinspired, and may also inform the as-yet undetermined biosynthesis of several congeners. |
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| معلومات مُعتمدة: | R01 GM086374 United States GM NIGMS NIH HHS; S10 RR023679 United States RR NCRR NIH HHS; S10 RR027172 United States RR NCRR NIH HHS; P41 GM068933 United States GM NIGMS NIH HHS; S10 OD023532 United States OD NIH HHS |
| سلسلة جزيئية: | PubChem-Substance 341098629; 341098640; 341098648; 341098649; 341098650; 341098651; 341098652; 341098653; 341098654; 341098630; 341098631; 341098632; 341098633; 341098634; 341098635; 341098636; 341098637; 341098638; 341098639; 341098641; 341098642; 341098643; 341098644; 341098645; 341098646; 341098647; 341100814; 341100816; 341100817; 341100818; 341100819; 341100820; 341100821; 341100822; 341100823; 341100824; 341100815 |
| المشرفين على المادة: | 0 (Biological Products) 0 (Indole Alkaloids) 0 (stephacidin A) |
| تواريخ الأحداث: | Date Created: 20171220 Date Completed: 20190409 Latest Revision: 20200306 |
| رمز التحديث: | 20240628 |
| مُعرف محوري في PubMed: | PMC6317722 |
| DOI: | 10.1038/nchem.2862 |
| PMID: | 29256515 |
| قاعدة البيانات: | MEDLINE |
Find this article in full text from Springer Verlag. 
Full Text Finder | تدمد: | 1755-4349 |
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| DOI: | 10.1038/nchem.2862 |