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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Scope of the 2(5H)-furanone helicity rule: a combined ECD, VCD, and DFT investigation

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Author(s):
dos Santos, Jr., Fernando M. [1] ; Bicalho, Keylla U. [2] ; Calisto, Italo H. [1] ; Scatena, Gabriel S. [1] ; Fernandes, Joao B. [1] ; Cass, Quezia B. [1] ; Batista, Jr., Joao M. [3, 1]
Total Authors: 7
Affiliation:
[1] Fed Univ Sao Carlos UFSCar, Dept Chem, BR-13565905 Sao Carlos, SP - Brazil
[2] Sao Paulo State Univ UNESP, Inst Chem, BR-14800060 Araraquara, SP - Brazil
[3] Fed Univ Sao Paulo UNIFESP, Inst Sci & Technol, BR-12231280 Sao Jose Dos Campos, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 16, n. 24, p. 4509-4516, JUN 28 2018.
Web of Science Citations: 6
Abstract

One of the most widely used methods to assess the stereochemistry of chiral 2(5H)-furanones is an empirical electronic circular dichroism (ECD) helicity rule. In the present work, an extensive experimental and theoretical investigation of the scope of the above-mentioned empirical rule for acetogenins with a hydroxyl group substituted at C-4 revealed a possible exception to this rule. The underlying causes for this observation are discussed with respect to side chain substitutions, conformational requirements, chromophore handedness as well as a qualitative orbital analysis. Further investigation using vibrational circular dichroism (VCD) spectroscopy led to the identification of spectral markers that seem to be more localized and less affected by side chain substitutions. As the presence of a ?-lactone ring and a hydroxyl group at C-4 is a very common structural feature of Annonaceous acetogenins, we recommend the combined use of ECD and VCD spectroscopy, along with quantum chemical computations, for the stereochemical analysis of structurally related molecules. (AU)

FAPESP's process: 15/07089-2 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules ánd macromolecules
Grantee:João Marcos Batista Junior
Support type: Scholarships in Brazil - Young Researchers
FAPESP's process: 12/25299-6 - Integrated studies for leaf cutting control
Grantee:João Batista Fernandes
Support type: Research Projects - Thematic Grants
FAPESP's process: 14/25222-9 - Vibrational chiroptical spectroscopy for stereochemical characterization of small molecules and macromolecules
Grantee:João Marcos Batista Junior
Support type: Research Grants - Young Investigators Grants
FAPESP's process: 13/01710-1 - Enzyme ligand: new models of screening
Grantee:Quezia Bezerra Cass
Support type: Research Projects - Thematic Grants
FAPESP's process: 16/23794-0 - Stereochemistry of complex natural compounds by vibrational optical activity: acetogenins
Grantee:Fernando Martins dos Santos Junior
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 10/18832-4 - Biomonitored studies of Spondia dulcis (Anacardiaceae), Annona montana ánd Rollinia mucosa (Annonaceae) against Atta Sexdens rubropilosa, Leucoagaricus gongylophorus ánd Sitophilus zeamais ánd development of nanoencapsulation processes
Grantee:Keylla Utherdyany Bicalho
Support type: Scholarships in Brazil - Doctorate