دورية أكاديمية
Computationally assisted assignment of kahalalide Y configuration using an NMR-constrained conformational search.
| العنوان: | Computationally assisted assignment of kahalalide Y configuration using an NMR-constrained conformational search. |
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| المؤلفون: | Albadry MA; Departments of Pharmacognosy, Pharmacology, Chemistry, and Biochemistry and National Center for Natural Products Research, School of Pharmacy, University of Mississippi, MS 38677, United States., Elokely KM, Wang B, Bowling JJ, Abdelwahab MF, Hossein MH, Doerksen RJ, Hamann MT |
| المصدر: | Journal of natural products [J Nat Prod] 2013 Feb 22; Vol. 76 (2), pp. 178-85. Date of Electronic Publication: 2013 Jan 30. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Society of Pharmacognosy Country of Publication: United States NLM ID: 7906882 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6025 (Electronic) Linking ISSN: 01633864 NLM ISO Abbreviation: J Nat Prod Subsets: MEDLINE |
| أسماء مطبوعة: | Original Publication: Cincinnati, American Society of Pharmacognosy. |
| مواضيع طبية MeSH: | Models, Chemical*, Depsipeptides/*chemistry , Depsipeptides/*isolation & purification , Mollusca/*chemistry, Animals ; Hawaii ; Hydrogen Bonding ; Molecular Conformation ; Nuclear Magnetic Resonance, Biomolecular/methods ; Stereoisomerism |
| مستخلص: | Assignment of the absolute configuration of cyclic peptides frequently yields challenges, leaving one or more stereogenic centers unassigned due to small quantities of sample and the limited utility of Marfey's or other methods for assigning amino or hydroxy acids. Here, we report isolation of kahalalide Y (1) from Bryopsis pennata for the first time; in addition, the application of a combination of molecular modeling and NOE distance constraint calculations was utilized to determine the conformation of 1 and the absolute configuration of the final stereogenic center of 1. Using the Schrödinger suite, the structure of 1 was sketched in Maestro and minimized using the OPLS2005 force field in Macromodel. A conformational search was performed separately for structures having an R or S configuration at C-3 of the beta-hydroxy fatty acid subunit that completes the cyclic scaffold of 1, after which multiple minimizations for all generated conformers were carried out. The lowest energy conformers of R and S stereoisomers were then subjected to B3LYP geometry optimizations including solvent effects. The S stereoisomer was shown to be in excellent agreement with the NOE-derived distance constraints and hydrogen-bonding stability studies. |
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| معلومات مُعتمدة: | C06 RR014503 United States RR NCRR NIH HHS; R01 AT007318 United States AT NCCIH NIH HHS |
| المشرفين على المادة: | 0 (Depsipeptides) 0 (kahalalide Y) |
| تواريخ الأحداث: | Date Created: 20130201 Date Completed: 20130426 Latest Revision: 20240513 |
| رمز التحديث: | 20240513 |
| مُعرف محوري في PubMed: | PMC3583380 |
| DOI: | 10.1021/np3006088 |
| PMID: | 23363083 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6025 |
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| DOI: | 10.1021/np3006088 |