Simultaneous Determination of the Conformation and Relative Configuration of Archazolide A by Using Nuclear Overhauser Effects,J Couplings, and Residual Dipolar Couplings

2008 ◽  
Vol 120 (20) ◽  
pp. 3782-3786 ◽  
Author(s):  
Christophe Farès ◽  
Jorma Hassfeld ◽  
Dirk Menche ◽  
Teresa Carlomagno
Keyword(s):  
Simultaneous Determination ◽  
Residual Dipolar Couplings ◽  
Dipolar Couplings ◽  
Relative Configuration ◽  
Nuclear Overhauser ◽  
Nuclear Overhauser Effects

Determination of the Relative Configuration of β-Amino Acid Esters Based on Residual Dipolar Couplings

2015 ◽  
Vol 2015 (31) ◽  
pp. 6801-6805 ◽  
Author(s):  
Thomas Niklas ◽  
Christian Steinmetzger ◽  
Weiping Liu ◽  
Daniel Zell ◽  
Dietmar Stalke ◽  
...  
Keyword(s):  
Amino Acid ◽  
Residual Dipolar Couplings ◽  
Dipolar Couplings ◽  
Amino Acid Esters ◽  
Relative Configuration ◽  
Acid Esters

scholarly journals Relative configuration of micrograms of natural compounds using proton residual chemical shift anisotropy

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Nilamoni Nath ◽  
Juan Carlos Fuentes-Monteverde ◽  
Dawrin Pech-Puch ◽  
Jaime Rodríguez ◽  
Carlos Jiménez ◽  
...  
Keyword(s):  
Chemical Shift ◽  
Residual Dipolar Couplings ◽  
Chemical Shift Anisotropy ◽  
Dipolar Couplings ◽  
Structural Determination ◽  
Proton Proton ◽  
Relative Configuration ◽  
Similar Information ◽  
3D Molecular Structure

Abstract 3D molecular structure determination is a challenge for organic compounds or natural products available in minute amounts. Proton/proton and proton/carbon correlations yield the constitution. J couplings and NOEs oftentimes supported by one-bond 1H,13C residual dipolar couplings (RDCs) or by 13C residual chemical shift anisotropies (RCSAs) provide the relative configuration. However, these RDCs or carbon RCSAs rely on 1% natural abundance of 13C preventing their use for compounds available only in quantities of a few 10’s of µgs. By contrast, 1H RCSAs provide similar information on spatial orientation of structural moieties within a molecule, while using the abundant 1H spin. Herein, 1H RCSAs are accurately measured using constrained aligning gels or liquid crystals and applied to the 3D structural determination of molecules with varying complexities. Even more, deuterated alignment media allow the elucidation of the relative configuration of around 35 µg of a briarane compound isolated from Briareum asbestinum.

Simultaneous Determination of Protein Backbone Structure and Dynamics from Residual Dipolar Couplings

2006 ◽  
Vol 128 (47) ◽  
pp. 15100-15101 ◽  
Author(s):  
Guillaume Bouvignies ◽  
Phineus Markwick ◽  
Rafael Brüschweiler ◽  
Martin Blackledge
Keyword(s):  
Simultaneous Determination ◽  
Residual Dipolar Couplings ◽  
Dipolar Couplings ◽  
Protein Backbone ◽  
Structure And Dynamics ◽  
Backbone Structure

Determination of the Relative Configuration of a Five-Membered Lactone from Residual Dipolar Couplings

2006 ◽  
Vol 45 (27) ◽  
pp. 4455-4460 ◽  
Author(s):  
Christina M. Thiele ◽  
Andreas Marx ◽  
Robert Berger ◽  
Jana Fischer ◽  
Markus Biel ◽  
...  
Keyword(s):  
Residual Dipolar Couplings ◽  
Dipolar Couplings ◽  
Relative Configuration

A Novel Method for the Determination of Stereochemistry in Six-Membered Chairlike Rings Using Residual Dipolar Couplings

2003 ◽  
Vol 68 (5) ◽  
pp. 1786-1795 ◽  
Author(s):  
Jiangli Yan ◽  
Allen D. Kline ◽  
Huaping Mo ◽  
Michael J. Shapiro ◽  
Edward R. Zartler
Keyword(s):  
Residual Dipolar Couplings ◽  
Dipolar Couplings ◽  
Novel Method

scholarly journals Determination of the Structures of Symmetric Protein Oligomers from NMR Chemical Shifts and Residual Dipolar Couplings

2011 ◽  
Vol 133 (16) ◽  
pp. 6288-6298 ◽  
Author(s):  
Nikolaos G. Sgourakis ◽  
Oliver F. Lange ◽  
Frank DiMaio ◽  
Ingemar André ◽  
Nicholas C. Fitzkee ◽  
...  
Keyword(s):  
Residual Dipolar Couplings ◽  
Chemical Shifts ◽  
Dipolar Couplings ◽  
Nmr Chemical Shifts

scholarly journals In Silico Modeling of Spirolides and Gymnodimines: Determination of S Configuration at Butenolide Ring Carbon C-4

Toxins ◽  
2020 ◽  
Vol 12 (11) ◽  
pp. 685
Author(s):  
Christian Zurhelle ◽  
Tilmann Harder ◽  
Urban Tillmann ◽  
Jan Tebben
Keyword(s):  
In Silico ◽  
Density Functional ◽  
Nuclear Overhauser Effect ◽  
Resonance Spectroscopy ◽  
Functional Theory ◽  
Relative Configuration ◽  
Overhauser Effect ◽  
In Silico Modeling ◽  
Nuclear Overhauser

Only few naturally occurring cyclic imines have been fully structurally elucidated or synthesized to date. The configuration at the C-4 carbon plays a pivotal role in the neurotoxicity of many of these metabolites, for example, gymnodomines (GYMs) and spirolides (SPXs). However, the stereochemistry at this position is not accessible by nuclear Overhauser effect—nuclear magnetic resonance spectroscopy (NOE-NMR) due to unconstrained rotation of the single carbon bond between C-4 and C-5. Consequently, the relative configuration of GYMs and SPXs at C-4 and its role in protein binding remains elusive. Here, we determined the stereochemical configuration at carbon C-4 in the butenolide ring of spirolide- and gymnodimine-phycotoxins by comparison of measured 13C NMR shifts with values obtained in silico using force field, semiempirical and density functional theory methods. This comparison demonstrated that modeled data support S configuration at C-4 for all studied SPXs and GYMs, suggesting a biosynthetically conserved relative configuration at carbon C-4 among these toxins.

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