Residual Dipolar Couplings in Structure Determination of Natural Products

Overview

Journal Nat Prod Bioprospect

Publisher Springer

Specialty Biology

Date 2018 Jun 27

PMID 29943349

Citations 12

Authors

Gao-Wei Li

Han Liu

Feng Qiu

Xiao-Juan Wang

Xin-Xiang Lei

Affiliations

Soon will be listed here.

Abstract

The determination of natural products stereochemistry remains a formidable task. Residual dipolar couplings (RDCs) induced by anisotropic media are a powerful tool for determination of the stereochemistry of organic molecule in solution. This review will provide a short introduction on RDCs-based methodology for the structural elucidation of natural products. Special attention is given to the current availability of alignment media in organic solvents. The applications of RDCs for structural analysis of some examples of natural products were discussed and summarized. This review provides a short introduction on RDCs-based methodology for the structural elucidation of natural products. Special attention is given to the current availability of alignment media in organic solvents. The applications of RDCs for structural analysis of some examples of natural products were discussed and summarized.

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References

Schmidts V, Fredersdorf M, Lubken T, Porzel A, Arnold N, Wessjohann L . RDC-based determination of the relative configuration of the fungicidal cyclopentenone 4,6-diacetylhygrophorone A12. J Nat Prod. 2013; 76(5):839-44. DOI: 10.1021/np300728b. View

Navarro-Vazquez A, Santamaria-Fernandez R, Sardina F . MSpin-JCoupling. A modular program for prediction of scalar couplings and fast implementation of Karplus relationships. Magn Reson Chem. 2017; 56(6):505-512. DOI: 10.1002/mrc.4667. View

Losonczi J, Andrec M, Fischer M, Prestegard J . Order matrix analysis of residual dipolar couplings using singular value decomposition. J Magn Reson. 1999; 138(2):334-42. DOI: 10.1006/jmre.1999.1754. View

Schmidt M, Sun H, Leonov A, Griesinger C, Reinscheid U . Chiral discrimination of amines by anisotropic NMR parameters using chiral polyacrylamide-based gels. Magn Reson Chem. 2013; 50 Suppl 1:S38-44. DOI: 10.1002/mrc.3886. View

Schuetz A, Junker J, Leonov A, Lange O, Molinski T, Griesinger C . Stereochemistry of sagittamide A from residual dipolar coupling enhanced NMR. J Am Chem Soc. 2007; 129(49):15114-5. DOI: 10.1021/ja075876l. View

Reller M, Wesp S, Koos M, Reggelin M, Luy B . Biphasic Liquid Crystal and the Simultaneous Measurement of Isotropic and Anisotropic Parameters by Spatially Resolved NMR Spectroscopy. Chemistry. 2017; 23(54):13351-13359. DOI: 10.1002/chem.201702126. View

Klochkov V, Klochkov A, Thiele C, Berger S . A novel liquid crystalline system for partial alignment of polar organic molecules. J Magn Reson. 2005; 179(1):58-63. DOI: 10.1016/j.jmr.2005.09.012. View

Cornilescu G, Ramos Alvarenga R, Wyche T, Bugni T, Gil R, Cornilescu C . Progressive Stereo Locking (PSL): A Residual Dipolar Coupling Based Force Field Method for Determining the Relative Configuration of Natural Products and Other Small Molecules. ACS Chem Biol. 2017; 12(8):2157-2163. PMC: 5712214. DOI: 10.1021/acschembio.7b00281. View

Schwalbe H, Marino J, King G, Wechselberger R, Bermel W, Griesinger C . Determination of a complete set of coupling constants in 13C-labeled oligonucleotides. J Biomol NMR. 1994; 4(5):631-44. DOI: 10.1007/BF00404274. View

10.

Luy B, Kobzar K, Kessler H . An easy and scalable method for the partial alignment of organic molecules for measuring residual dipolar couplings. Angew Chem Int Ed Engl. 2004; 43(9):1092-4. DOI: 10.1002/anie.200352860. View

11.

Leyendecker M, Meyer N, Thiele C . Development of New Supramolecular Lyotropic Liquid Crystals and Their Application as Alignment Media for Organic Compounds. Angew Chem Int Ed Engl. 2017; 56(38):11471-11474. DOI: 10.1002/anie.201705642. View

12.

Thiele C, Marx A, Berger R, Fischer J, Biel M, Giannis A . Determination of the relative configuration of a five-membered lactone from residual dipolar couplings. Angew Chem Int Ed Engl. 2006; 45(27):4455-60. DOI: 10.1002/anie.200503247. View

13.

Merle C, Kummerlowe G, Freudenberger J, Halbach F, Stower W, Gostomski C . Crosslinked poly(ethylene oxide) as a versatile alignment medium for the measurement of residual anisotropic NMR parameters. Angew Chem Int Ed Engl. 2013; 52(39):10309-12. DOI: 10.1002/anie.201301929. View

14.

Rigling C, Ebert M . RDC-enhanced structure calculation of a β-heptapeptide in methanol. Magn Reson Chem. 2016; 55(7):655-661. DOI: 10.1002/mrc.4569. View

15.

Moskalenko Y, Bagutski V, Thiele C . Chemically synthesized and cross-linked PDMS as versatile alignment medium for organic compounds. Chem Commun (Camb). 2016; 53(1):95-98. DOI: 10.1039/c6cc08762k. View

16.

Dama M, Berger S . Polyisocyanides as a new alignment medium to measure residual dipolar couplings for small organic molecules. Org Lett. 2011; 14(1):241-3. DOI: 10.1021/ol202547y. View

17.

Milanowski D, Oku N, Cartner L, Bokesch H, Williamson R, Sauri J . Unequivocal determination of caulamidines A and B: application and validation of new tools in the structure elucidation tool box. Chem Sci. 2018; 9(2):307-314. PMC: 5868047. DOI: 10.1039/c7sc01996c. View

18.

Li G, Cao J, Zong W, Hu L, Hu M, Lei X . Helical Polyisocyanopeptides as Lyotropic Liquid Crystals for Measuring Residual Dipolar Couplings. Chemistry. 2017; 23(32):7653-7656. DOI: 10.1002/chem.201700539. View

19.

Schuetz A, Murakami T, Takada N, Junker J, Hashimoto M, Griesinger C . RDC-enhanced NMR spectroscopy in structure elucidation of sucro-neolambertellin. Angew Chem Int Ed Engl. 2008; 47(11):2032-4. DOI: 10.1002/anie.200705037. View

20.

Thiele C . Simultaneous assignment of all diastereotopic protons in strychnine using RDCs: PELG as alignment medium for organic molecules. J Org Chem. 2004; 69(22):7403-13. DOI: 10.1021/jo049867w. View