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Absolute Configurations of Four Resorcylic Acid Lactones, Paecilomycins J − M, by CD/TDDFT Calculations
Author(s) -
Xu LiangXiong,
Xue JingHua,
Wu Ping,
You XiaoYing,
Wei XiaoYi
Publication year - 2014
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22264
Subject(s) - chemistry , time dependent density functional theory , circular dichroism , chirality (physics) , cotton effect , density functional theory , absolute configuration , spectral line , stereochemistry , yield (engineering) , crystallography , computational chemistry , chiral symmetry , physics , materials science , astronomy , metallurgy , quantum mechanics , nambu–jona lasinio model , quark
The absolute configurations of four resorcylic acid lactones (RALs), paecilomycins J − M ( 1 − 3 and 5 ), were assigned by Time‐Dependent Density‐Functional Theory (TDDFT) calculations of their electronic circular dichroism (CD) spectra. The previously reported structure 4 for paecilomycin M was found to be incorrect and should be changed to structure 5 . Analysis of structure‐spectrum relationship for this group of RALs suggested that V′‐shape conformations give type I CD spectra (two negative Cotton effects around 300 and 260 nm, a positive Cotton effect around 220 nm) while V‐shape conformations yield type II spectra (signs of three Cotton effects were opposite to those in type I). Chirality 26:44–50, 2013 . © 2013 Wiley Periodicals, Inc.