TY - JOUR
T1 - Enantiomeric characterization and structure elucidation of LH601A using vibrational circular dichroism spectroscopy
AU - Shen, Jian
AU - Magesh, Sadagopan
AU - Chen, Lin
AU - Hu, Longqin
AU - He, Yanan
N1 - Funding Information:
This work used the Extreme Science and Engineering Discovery Environment (XSEDE), which is supported by National Science Foundation grant number ACI-1053575. We gratefully acknowledge the financial support of grants CA133791 and MH093197 from the National Institutes of Health .
Publisher Copyright:
© 2017
PY - 2018/3/5
Y1 - 2018/3/5
N2 - LH601A is a novel non-reactive chiral molecule inhibiting Keap1-Nrf2 protein-protein interaction. The absolute configuration (AC) was independently determined in this study using vibrational circular dichroism (VCD) spectroscopy. Because of band overlapping and broadening in the IR spectrum, a direct VCD spectrum comparison method is devised without the conventional IR band alignment. Being an unbiased AC inquiry, all possible chiralities are evaluated based on the statistical analysis of VCD similarity, Sv. The AC of three-center stereoisomer LH601A is unambiguously assigned to (S,R,S). A comparative study was also carried out to investigate the structural and energy differences of calculated conformers using the polarized continuum model of dimethyl sulfoxide.
AB - LH601A is a novel non-reactive chiral molecule inhibiting Keap1-Nrf2 protein-protein interaction. The absolute configuration (AC) was independently determined in this study using vibrational circular dichroism (VCD) spectroscopy. Because of band overlapping and broadening in the IR spectrum, a direct VCD spectrum comparison method is devised without the conventional IR band alignment. Being an unbiased AC inquiry, all possible chiralities are evaluated based on the statistical analysis of VCD similarity, Sv. The AC of three-center stereoisomer LH601A is unambiguously assigned to (S,R,S). A comparative study was also carried out to investigate the structural and energy differences of calculated conformers using the polarized continuum model of dimethyl sulfoxide.
KW - Polarized continuum model
KW - SIMVCD
KW - Spectrum similarity
KW - Vibrational circular dichroism
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U2 - 10.1016/j.saa.2017.11.033
DO - 10.1016/j.saa.2017.11.033
M3 - Article
C2 - 29172127
AN - SCOPUS:85034454517
SN - 1386-1425
VL - 192
SP - 312
EP - 317
JO - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
JF - Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
ER -