The stereochemical assignment of acyclic polyols: a computational study of the NMR data of a library of stereopentad sequences from polyketide natural products

Smith, Steven G.; Channon, Julia A.; Paterson, Ian; Goodman, Jonathan M.

doi:10.1016/j.tet.2010.06.022

Cited by 26 publications

(31 citation statements)

References 62 publications

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“…Beside helping in the assignment of spectra, computed spectra have also been used to determine the stereochemistry of natural compounds. Generally, such a task is very difficult, but computational NMR calculations can simplify this process and reliably assign stereochemistry with quantifiable confidence …”

Section: Jaguar Featuresmentioning

confidence: 99%

Jaguar: A high‐performance quantum chemistry software program with strengths in life and materials sciences

Bochevarov

Harder

Hughes

et al. 2013

Int J of Quantum Chemistry

1,554

1,162

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Jaguar is an ab initio quantum chemical program that specializes in fast electronic structure predictions for molecular systems of medium and large size. Jaguar focuses on computational methods with reasonable computational scaling with the size of the system, such as density functional theory (DFT) and local secondorder Mïller-Plesset perturbation theory. The favorable scaling of the methods and the high efficiency of the program make it possible to conduct routine computations involving several thousand molecular orbitals. This performance is achieved through a utilization of the pseudospectral approximation and several levels of parallelization. The speed advantages are beneficial for applying Jaguar in biomolecular computational modeling. Additionally, owing to its superior wave function guess for transition-metalcontaining systems, Jaguar finds applications in inorganic and bioinorganic chemistry. The emphasis on larger systems and transition metal elements paves the way toward developing Jaguar for its use in materials science modeling. The article describes the historical and new features of Jaguar, such as improved parallelization of many modules, innovations in ab initio pKa prediction, and new semiempirical corrections for nondynamic correlation errors in DFT. Jaguar applications in drug discovery, materials science, force field parameterization, and other areas of computational research are reviewed. Timing benchmarks and other results obtained from the most recent Jaguar code are provided. The article concludes with a discussion of challenges and directions for future development of the program.

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Section: Jaguar Featuresmentioning

confidence: 99%

Jaguar: A high‐performance quantum chemistry software program with strengths in life and materials sciences

Bochevarov

Harder

Hughes

et al. 2013

Int J of Quantum Chemistry

1,554

1,162

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“…This being said, we found that the CP3 parameter was used in solving structural problems in several studies . Interestingly, only in 33 % of the cases were the NMR shielding tensors computed at the level of theory reported in the seminal publication (B3LYP/6‐31G(d,p)//MMFF) –. In the remaining 67 %, the geometry optimization steps was conducted at higher levels, such as B3LYP or mPW1PW91 DFT functionals, coupled with double‐ or triple‐ζ basis sets –.…”

Section: Cp3mentioning

confidence: 99%

“…In 2010, one year after the publication of CP3, the Goodman group in collaboration with the Paterson group (both from Cambridge University), reported the synthesis of the 16 possible stereopentads 9 (Figure ), bearing a common substitution pattern found in many natural products . After an in depth analysis of the similarity of the experimental NMR spectra of all isomers, the corresponding GIAO NMR calculations were carried out at the B3LYP/6‐31G(d,p)//MMFF level.…”

Section: Cp3mentioning

confidence: 99%

“…With the complete set of experimental and computational data, all possible 120 pairs were matched and the corresponding CP3 parameters were computed. Notably, the CP3 performed very well, correctly assigning 99 pairs in high confidence, and failing only in 2 cases (by selecting the wrong match in high probability) . To date, this work is one of the most remarkable examples of the robustness of a computational methodology to help in the stereoassignment of closely related molecules.…”

Section: Cp3mentioning

confidence: 99%

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Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Grimblat

Sarotti

2016

Chemistry A European J

193

147

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The calculations of NMR properties of molecules using quantum chemical methods have deeply impacted several branches of organic chemistry. They are particularly important in structural or stereochemical assignments of organic compounds, with implications in total synthesis, stereoselective reactions, and natural products chemistry. In studying the evolution of the strategies developed to support (or reject) a structural proposal, it becomes clear that the most effective and accurate ones involve sophisticated procedures to correlate experimental and computational data. Owing to their relatively high mathematical complexity, such calculations (CP3, DP4, ANN-PRA) are often carried out using additional computational resources provided by the authors (such as applets or Excel files). This Minireview will cover the state-of-the-art of these toolboxes in the assignment of organic molecules, including mathematical definitions, updates, and discussion of relevant examples.

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“…Esse cancelamento dos erros sistemáticos ocorre devido ao fato de que as diferenças entre os deslocamentos químicos de núcleos equivalentes são melhores reproduzidas pelos cálculos computacionais do que os valores absolutos dos deslocamentos químicos. O parâmetro de comparação CP3 tem sido aplicado na determinação da configuração relativa de diversos compostos naturais e sintéticos [84][85][86][87][88][89][90][91][92][93][94][95][96][97][98][99][100][101].…”

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Síntese de Î-butirolactonas por processo multicomponente, modificações estruturais e estudo estereoquímico

Previdi¹

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DedicatóriaDedico esta tese à minha família que tanto amo, Ao meu pai, Fábio, e à minha mãe, Madalena, aos quais admiro imensamente e que sempre me deram todo o apoio possível para seguir em meus estudos, sempre me incentivaram e deram conselhos, exemplos e orientações que me fizeram crescer muito. À minha irmã, Poliana, por sempre ter sido uma grande amiga participando de minha vida e me ajudando em todos os momentos difíceis. À minha noiva, Cristiane, por seu amor, carinho, alegria e paciência durante esses anos que estamos juntos, além, é claro, dos sonhos e planos para o futuro que me motivam a lutar cada vez mais.Aos meus familiares e amigos, que me proporcionam momentos felizes e de alegria e que de alguma forma contribuíram e me apoiaram durante esses anos. Síntese de -butirolactonas por processo multicomponente, modificações estruturais e estudo estereoquímico _________________________________________________________________________________________________________________ _________________________________________________________________________________________________________________ Agradecimentos Agradecimentos A Deus; Ao Prof. Dr. Paulo Marcos Donate, por sua orientação, dedicação, paciência durante todos esses anos e pelo incentivo e apoio no desenvolvimento desta tese de doutorado. Ao Prof. Dr. Gil Valdo José da Silva, pela amizade e colaboração em parte deste trabalho; Ao Prof. Dr. Antônio Eduardo Miller Crotti, pelos conselhos, amizade e análises por cromatografia em fase gasosa acoplada a espectrometria de massas; Ao Prof. Dr. Luiz Alberto Beraldo de Moraes e ao químico Dr. Eduardo José Crevelin, pela ajuda nas análises e purificações por cromatografia líquida de alta eficiência; À Dra. Viviani Nardini Takahashi pela colaboração nos estudos envolvendo química computacional, discussões e amizade; Ao meu amigo e químico responsável pelo RMN, Vinícius Palaretti, pela colaboração em parte desse trabalho, pela competência na obtenção dos espectros de RMN e principalmente pelo apoio e amizade; Aos alunos de iniciação científica Mayla e Mike pela colaboração direta nos trabalhos desta tese de doutorado e pela amizade; Aos meus grandes amigos do LSO e visitantes em algum momento, Alexandre, Carlismari, Wesley pelo companheirismo, apoio, conselhos e pela grande ajuda nos trabalhos rotineiros do laboratório; Aos funcionários do Departamento de Química e da Seção de Pós-Graduação da FFCLRP, por toda atenção e ajuda; Síntese de -butirolactonas por processo multicomponente, modificações estruturais e estudo estereoquímico _________________________________________________________________________________________________________________ _________________________________________________________________________________________________________________ Agradecimentos A todos os docentes do Departamento de Química, que contribuíram com minha formação; A todos que contribuíram, direta ou indiretamente, na execução deste trabalho, meus sinceros agradecimentos; À CAPES e ao CNPq, pelas bolsas concedidas e à FAPESP pelo...

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The stereochemical assignment of acyclic polyols: a computational study of the NMR data of a library of stereopentad sequences from polyketide natural products

Cited by 26 publications

References 62 publications

Jaguar: A high‐performance quantum chemistry software program with strengths in life and materials sciences

Jaguar: A high‐performance quantum chemistry software program with strengths in life and materials sciences

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Síntese de Î-butirolactonas por processo multicomponente, modificações estruturais e estudo estereoquímico

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The stereochemical assignment of acyclic polyols: a computational study of the NMR data of a library of stereopentad sequences from polyketide natural products

Cited by 26 publications

References 62 publications

Jaguar: A high‐performance quantum chemistry software program with strengths in life and materials sciences

Jaguar: A high‐performance quantum chemistry software program with strengths in life and materials sciences

Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations

Sí­ntese de Î-butirolactonas por processo multicomponente, modificações estruturais e estudo estereoquí­mico

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Síntese de Î-butirolactonas por processo multicomponente, modificações estruturais e estudo estereoquímico