TY - JOUR
T1 - Absolute configuration of eremophilanoids by vibrational circular dichroism
AU - Burgueño-Tapia, Eleuterio
AU - Joseph-Nathan, Pedro
N1 - Funding Information:
Financial support from SIP-IPN and CONACYT-Mexico is acknowledged.
PY - 2008/8
Y1 - 2008/8
N2 - The absolute configurations (AC) of natural occurring 6-hydroxyeuryopsin (1), of its acetyl derivative 2, and of eremophilanolide 8 were confirmed by comparison of the experimental vibrational circular dichroism (VCD) spectra with theoretical curves generated from density functional theory (DFT) calculations. Initial analyses were carried out using a Monte Carlo searching with the MMFF94 molecular mechanics force field. All MMFF94 conformers were further optimized using DFT at the B3LYP/6-31G(d) level of theory, followed by calculations of their vibrational frequencies at the B3LYP/6-31G(d,p); the VCD spectra of 2 and 8 were also calculated at the B3PW91/DGDZVP level of theory. Good agreement between theoretical and experimental VCD curves unambiguously verified the 4S,5R,6S absolute configuration for 1 and 2, and the 1S,4S,5R,6S,8S,10S configuration for 8.
AB - The absolute configurations (AC) of natural occurring 6-hydroxyeuryopsin (1), of its acetyl derivative 2, and of eremophilanolide 8 were confirmed by comparison of the experimental vibrational circular dichroism (VCD) spectra with theoretical curves generated from density functional theory (DFT) calculations. Initial analyses were carried out using a Monte Carlo searching with the MMFF94 molecular mechanics force field. All MMFF94 conformers were further optimized using DFT at the B3LYP/6-31G(d) level of theory, followed by calculations of their vibrational frequencies at the B3LYP/6-31G(d,p); the VCD spectra of 2 and 8 were also calculated at the B3PW91/DGDZVP level of theory. Good agreement between theoretical and experimental VCD curves unambiguously verified the 4S,5R,6S absolute configuration for 1 and 2, and the 1S,4S,5R,6S,8S,10S configuration for 8.
KW - 1α-Angeloyloxy-8β,10β-dihydroxyeremophil-7(11)-en- 8α,12-olide
KW - 6-Acetyloxyeuryopsin
KW - 6-Hydroxyeuryopsin
KW - Absolute configuration
KW - Vibrational circular dichroism
UR - http://www.scopus.com/inward/record.url?scp=48349127385&partnerID=8YFLogxK
U2 - 10.1016/j.phytochem.2008.05.011
DO - 10.1016/j.phytochem.2008.05.011
M3 - Artículo
SN - 0031-9422
VL - 69
SP - 2251
EP - 2256
JO - Phytochemistry
JF - Phytochemistry
IS - 11
ER -