Absolute Configuration Reassignment of Natural Products: An Overview of the Last Decade

Author(s)

Batista, Andrea N. L. ^[1] ; Angrisani, Bianca R. P. ^[1] ; Lima, Maria Emanuelle D. ^[1] ; da Silva, Stephanie M. P. ^[1] ; Schettini, Vitoria H. ^[1] ; Chagas, Higor A. ^[1] ; dos Santos, Jr., Fernando M. ^[1] ; Batista, Jr., Joao M. ^[2] ; Valverde, Alessandra L. ^[1]

Affiliation

^[1] Univ Fed Fluminense, Inst Quim, Dept Quim Organ, Outeiro Sao Joao Batista S-N, BR-24020141 Niteroi, RJ - Brazil

^[2] Univ Fed Sao Paulo, Inst Ciencia & Tecnol, Dept Ciencia & Technol, Rua Talim 330, BR-12231280 Sao Jose Dos Campos, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 32, n. 8, p. 1499-1518, AUG 2021.
• Web of Science Citations: 0

Abstract

The assignment of absolute configuration (AC) is a crucial step in the structural characterization of natural products, especially for those subjected to biological assays. Methods such as X-ray crystallography, stereocontrolled organic synthesis, nuclear magnetic resonance (NMR), and chiroptical spectroscopies are commonly used to determine the AC of chiral natural compounds. Even with these well-established techniques, however, unambiguous stereochemical assignments of natural products remain a challenge, resulting in an increasing number of structural misassignments being reported every year. Herein, we will present the main techniques that have been used in AC reassignments of natural products over the last 10 years, along with some selected examples. Special attention will be paid to the strengths and weaknesses of each approach. With this, we expect to provide the readers with critical information to help them to choose the appropriate methods for correct AC determinations. (AU)

• FAPESP's process: 19/22319-5 - Vibrational circular dichroism spectral markers: facilitating absolute configuration assignment of natural products
• Grantee: João Marcos Batista Junior
• Support Opportunities: Regular Research Grants