Drawing Polycyclic Molecules

Tantillo, Dean J.

doi:10.1021/acsomega.1c03607

Cited by 2 publications

(2 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Drawing uncertainties like this one are ubiquitous in the natural product literature. We refer everyone interested in honing their structure drawing skills to an excellent piece by Tantillo, appropriately titled "Drawing Polycyclic Molecules" 50 (see the Supporting Information for more examples).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

DU8ML: Machine Learning-Augmented Density Functional Theory Nuclear Magnetic Resonance Computations for High-Throughput In Silico Solution Structure Validation and Revision of Complex Alkaloids

Novitskiy

Kutateladze

2022

J. Org. Chem.

View full text Add to dashboard Cite

Machine learning (ML) profoundly improves the accuracy of the fast DU8+ hybrid density functional theory/parametric computations of nuclear magnetic resonance spectra, allowing for high throughput in silico validation and revision of complex alkaloids and other natural products. Of nearly 170 alkaloids surveyed, 35 structures are revised with the next-generation ML-augmented DU8 method, termed DU8ML.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

DU8ML: Machine Learning-Augmented Density Functional Theory Nuclear Magnetic Resonance Computations for High-Throughput In Silico Solution Structure Validation and Revision of Complex Alkaloids

Novitskiy

Kutateladze

2022

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Finally, (±)-decumicorine A ( 1 ) and (±)- epi -decumicorine A ( 2 ), two pairs of enantiomeric isoquinoline alkaloids that contain a novel carbon framework of phenylpropanoid-conjugated protoberberine, were obtained (Fig. 1 ) (Tantillo 2021 ) from the aqueous layer of total alkaloids after partitioning with the organic solvent. Herein, we report the isolation, structural determination, plausible biosynthetic pathways, biomimetic synthesis, and anti-SARS-CoV-2 activity of these compounds.…”

Section: Introductionmentioning

confidence: 99%

Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens

Wang

Yang

et al. 2022

Arch. Pharm. Res.

View full text Add to dashboard Cite

(±)-Decumicorine A ( 1 ) and (±)- epi -decumicorine A ( 2 ), two pairs of enantiomeric isoquinoline alkaloids featuring a novel phenylpropanoid-conjugated protoberberine skeleton, were isolated and purified from the rhizomes of Corydalis decumbens . The separation of (±)- 1 and (±)- 2 was achieved by chiral HPLC to produce four optically pure enantiomers. The structures and absolute configurations of compounds (−)- 1 , (+)- 1 , (−)- 2 , and (+)- 2 were elucidated by spectroscopic analysis, ECD calculations, and X-ray crystallographic analyses. The two racemates were generated from a Diels-Alder [4 + 2] cycloaddition between jatrorrhizine and ferulic acid in the proposed biosynthetic pathways, which were fully verified by a biomimetic synthesis. Moreover, compound (+)- 1 exhibited an antiviral entry effect on SARS-CoV-2 pseudovirus by blocking spike binding to the ACE2 receptor on HEK-293T-ACE2 h host cells. Supplementary Information The online version contains supplementary material available at 10.1007/s12272-022-01401-6.

show abstract

Drawing Polycyclic Molecules

Abstract: A personal perspective on the practice of drawing polycyclic molecules and its implications for understanding and undertaking chemistry is presented.

Cited by 2 publications

References 28 publications

DU8ML: Machine Learning-Augmented Density Functional Theory Nuclear Magnetic Resonance Computations for High-Throughput In Silico Solution Structure Validation and Revision of Complex Alkaloids

DU8ML: Machine Learning-Augmented Density Functional Theory Nuclear Magnetic Resonance Computations for High-Throughput In Silico Solution Structure Validation and Revision of Complex Alkaloids

Structures, biomimetic synthesis, and anti-SARS-CoV-2 activity of two pairs of enantiomeric phenylpropanoid-conjugated protoberberine alkaloids from the rhizomes of Corydalis decumbens

Contact Info

Product

Resources

About