Absolute Configurations of Four Resorcylic Acid Lactones, Paecilomycins J − M, by CD/TDDFT Calculations. Issue 1 (26th November 2013)

• Record Type: Journal Article
• Authors: Xu, Liang‐Xiong; Xue, Jing‐Hua; Wu, Ping; You, Xiao‐Ying; Wei, Xiao‐Yi
• Is Part Of: Chirality. Volume 26:Issue 1(2014:Jan.)
• Page Start: 44
• Page End: 50
• Publication Date: 2013-11-26
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22264
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>ABSTRACT</title> <p>The absolute configurations of four resorcylic acid lactones (RALs), paecilomycins J − M (<bold>1</bold>, <bold>2</bold>, <bold>3</bold> and <bold>5</bold>), were assigned by Time‐Dependent Density‐Functional Theory (TDDFT) calculations of their electronic circular dichroism (CD) spectra. The previously reported structure <bold>4</bold> for paecilomycin M was found to be incorrect and should be changed to structure <bold>5</bold>. 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). <italic>Chirality 26:44–50, 2013</italic>. © 2013 Wiley Periodicals, Inc.</p> </abstract>