Combining the Power of J Coupling and DP4 Analysis on Stereochemical Assignments: The J-DP4 Methods

被引：114

作者：

Grimblat, Nicolas ^{[1
,2
]}

Gavin, Jose A. ^{[3
]}

Hernandez Daranas, Antonio ^{[3
,4
]}

Sarotti, Ariel M. ^{[1
,2
]}

机构：

[1] Univ Nacl Rosario, CONICET, Inst Quim Rosario IQUIR, Suipacha 531,S2002LRK, Rosario, Santa Fe, Argentina

[2] Univ Nacl Rosario, Fac Ciencias Bioquim & Farmaceut, Suipacha 531,S2002LRK, Rosario, Santa Fe, Argentina

[3] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, E-38206 Tenerife, Spain

[4] CSIC, IPNA, Tenerife 38206, Spain

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 11期

关键词：

3D STRUCTURE ELUCIDATION; NMR CHEMICAL-SHIFTS; NATURAL-PRODUCTS; RELATIVE CONFIGURATION; DFT; CONSTANTS; REVISION; SPECTROSCOPY; VALIDATION;

D O I：

10.1021/acs.orglett.9b01193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A systematic study to include (3)J(HH) couplings into DP4 formalism (J-DP4) led to the development of three alternative strategies. The "dJ-DP4 (direct) approach involves a new DP4-like equation including an additional probability term given by (3)J(HH). The iJ-DP4 (indirect) approach explores the original DP4 method with a restricted conformational search. Despite both strategies performing better than DP4, their combined use (iJ/dJ-DP4) provided the best results, with a 2.5-fold performance improvement at similar or lower computational cost.

引用

页码：4003 / 4007

页数：5

共 29 条

[1] Quantum-Chemical Simulation of 1H NMR Spectra. 2. Comparison of DFT-Based Procedures for Computing Proton-Proton Coupling Constants in Organic Molecules [J].

Bally, Thomas ;

Rablen, Paul R. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12) :4818-4830

[2] Determination of relative configuration in organic compounds by NMR spectroscopy and computational methods [J].

Bifulco, Giuseppe ;

Dambruoso, Paolo ;

Gomez-Paloma, Luigi ;

Riccio, Raffaele .

CHEMICAL REVIEWS, 2007, 107 (09) :3744-3779

[3] Connecting Discrete Stereoclusters by Using DFT and NMR Spectroscopy: The Case of Nivariol [J].

Cen-Pacheco, Francisco ;

Rodriguez, Jaime ;

Norte, Manuel ;

Fernandez, Jose J. ;

Hernandez Daranas, Antonio .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (26) :8525-8532

[4] Recent trends in the structural revision of natural products [J].

Chhetri, Bhuwan Khatri ;

Lavoie, Serge ;

Sweeney-Jones, Anne Marie ;

Kubanek, Julia .

NATURAL PRODUCT REPORTS, 2018, 35 (06) :514-531

[5] Stereochemistry of Complex Marine Natural Products by Quantum Mechanical Calculations of NMR Chemical Shifts: Solvent and Conformational Effects on Okadaic Acid [J].

Dominguez, Humberto J. ;

Crespin, Guillermo D. ;

Santiago-Benitez, Adrian J. ;

Gavin, Jose A. ;

Norte, Manuel ;

Fernandez, Jose J. ;

Hernandez Daranas, Antonio .

MARINE DRUGS, 2014, 12 (01) :176-192

[6] Doubling the power of DP4 for computational structure elucidation [J].

Ermanis, K. ;

Parkes, K. E. B. ;

Agback, T. ;

Goodman, J. M. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (42) :8998-9007

[7] Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations [J].

Grimblat, Nicolas ;

Sarotti, Ariel M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (35) :12246-12261

[8] Beyond DP4: an Improved Probability for the Stereochemical Assignment of Isomeric Compounds using Quantum Chemical Calculations of NMR Shifts [J].

Grimblat, Nicolas ;

Zanardi, Maria M. ;

Sarotti, Ariel M. .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) :12526-12534

[9] New Bicyclotridecane C15 Nonterpenoid Bromoallenes from Laurencia marilzae [J].

Gutierrez-Cepeda, Adrian ;

Fernandez, Jose J. ;

Norte, Manuel ;

Souto, Maria L. .

ORGANIC LETTERS, 2011, 13 (10) :2690-2693

[10] Development of a Concise and General Enantioselective Approach to 2,5-Disubstituted-3-hydroxytetrahydrofurans [J].

Kang, Baldip ;

Mowat, Jeffrey ;

Pinter, Thomas ;

Britton, Robert .

ORGANIC LETTERS, 2009, 11 (08) :1717-1720

← 1 2 3 →