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Deconvolution of E/Z tetrahydroisoquinoline amide rotamers and conformers from a marine-derived Streptomyces strain |
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| Authors: | Vanessa M Nepomuceno Hiyoung Kim Yuanqing Ding Hongbing Liu Mark Sadek Daneel Ferreira Sesselja Omarsdottir Brian T Murphy |
| Institution: | 1. Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago, Chicago, IL, 60612, United States;2. Center for Biomolecular Sciences, University of Illinois at Chicago, Chicago, IL, 60607, United States;3. Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, 60612, United States;4. Faculty of Pharmaceutical Sciences, School of Health Sciences, University of Iceland, Reykjavik, IS-107, Iceland;5. National Center for Natural Products Research, University of Mississippi, University, MS 38677-1848, United States;6. Department of Biomolecular Sciences, Division of Pharmacognosy, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, University, MS, 38677-1848, United States |
| Abstract: | A collaborative program to discover new specialized metabolites from aquatic environments of Iceland led to the deconvolution of tetrahydroisoquinoline amide E/Z rotamers (E/Z)-N-acetyl-MY336-a; 1] and conformers produced by a Streptomyces sp. All structures were elucidated by NMR and MS analysis, and interpretation of electronic circular dichroism (ECD) data. ECD and optical rotation (OR) simulations permitted the unequivocal assignment of the absolute configuration of compound 1 and provided an important example of delineating the spectroscopic contributions of equilibrating rotamers and boat/chair conformers of a common natural product scaffold. |
| Keywords: | Tetrahydroisoquinoline Rotamers Natural products Streptomyces ECD |
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