𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism

✍ Scribed by Teresa B. Freedman; Xiaolin Cao; Regina V. Oliveira; Quezia B. Cass; Laurence A. Nafie

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
147 KB
Volume
15
Category
Article
ISSN
0899-0042

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

Vibrational circular dichroism (VCD) measurements and density functional theory (DFT) calculations were used to obtain the first definitive assignment of the absolute configuration for the polyphenolic binaphpthyl dialdehyde gossypol and a determination of the solution conformation in CDCl~3~. VCD spectra recorded for the two resolved enantiomers are near mirror images and excellent agreement between the observed IR and VCD spectra and intensity calculations carried out at the DFT (B3LYP/6‐31G*) level establish the absolute configurations of (+)‐gossypol as P and (βˆ’)‐gossypol as M, with two conformations in CDCl~3~ solution that differ in isopropyl group orientation. Chirality 15:196–200, 2003. Β© 2003 Wiley‐Liss, Inc.

πŸ“œ SIMILAR VOLUMES

Determination of the Absolute Configurat
Determination of the Absolute Configuration of (βˆ’)-Mirtazapine by Vibrational Circular Dichroism
✍ Teresaβ€…B. Freedman; Rinaβ€…K. Dukor; Peterβ€…J.β€…C.β€…M. vanβ€…Hoof; Edwinβ€…R. Kellenbach; πŸ“‚ Article πŸ“… 2002 πŸ› John Wiley and Sons 🌐 German βš– 92 KB πŸ‘ 1 views

The absolute configuration of the (Γ€)-enantiomer of mirtazapine was determined by means of vibrational circular dichroism (VCD). The observed VCD of (Γ€)-mirtazapine showed excellent correlation with the calculated VCD of the (R)-enantiomer. This is in agreement with the absolute configuration as det

Absolute configurations of brominated se
Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism
✍ Kenji Monde; Tohru Taniguchi; Nobuaki Miura; Charles S. Vairappan; Minoru Suzuki πŸ“‚ Article πŸ“… 2006 πŸ› John Wiley and Sons 🌐 English βš– 149 KB πŸ‘ 1 views

## Abstract Two brominated sesquiterpenes, majapolene B (**1**) and acetylmajapolene B (**2**), isolated from the red algal genus __Laurencia__ were investigated using vibrational circular dichroism (VCD). The ab initio theoretical VCD and IR calculations of **1** and **2** were performed by densit

Solution conformations of cyclosporins a
Solution conformations of cyclosporins and magnesium-cyclosporin complexes determined by vibrational circular dichroism
✍ Louise A. Bodack; Teresa B. Freedman; Babur Z. Chowdhry; Laurence A. Nafie πŸ“‚ Article πŸ“… 2004 πŸ› Wiley (John Wiley & Sons) 🌐 English βš– 262 KB πŸ‘ 1 views

## Abstract Vibrational circular dichroism (VCD) spectroscopy was used to investigate the solution conformations of cyclosporins A, C, D, G, and H in CDCl~3~, in the amide I and NH/OH‐stretching regions, and their corresponding magnesium complexes in CD~3~CN, in the amide I region. VCD spectra are