Issue 23, 2008
From the journal:

Organic & Biomolecular Chemistry

Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C

Tohru Taniguchi,a   Kenji Monde,*b   Koji Nakanishia  and  Nina Berova*a  

* Corresponding authors

a Department of Chemistry, Columbia University, New York, NY, USA
E-mail: ndb1@columbia.edu
Fax: +1-212-932-1289
Tel: +1-212-854-3934

b Graduate School of Advanced Life Science, Frontier Research Center for Post-Genome Science and Technology, Hokkaido University, N21W11, Sapporo, Japan
E-mail: kmonde@glyco.sci.hokudai.ac.jp
Fax: +81-11-706-9042
Tel: +81-11-706-9041

Abstract

The optical rotation, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) of chiral sulfinates have been studied experimentally, and analysed by density functional theory calculation, aiming at establishing a reliable and convenient methodology to determine their absolute configuration. Through the study on a model chiral sulfinate with known absolute configuration, (R)-(+)-methyl p-toluenesulfinate ((R)-(+)-1), each technique was found to be reliable in assigning chirality of sulfinates. We then applied these methods to a synthetically prepared cruciferous phytoalexin, brassicanal C ((−)-2), and unambiguously determined its absolute configuration as S. The advantages and disadvantages of each spectroscopy on sulfinates are also discussed.

Graphical abstract: Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C

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Article information

DOI
https://doi.org/10.1039/B813437E
Article type
Paper
Submitted
04 Aug 2008
Accepted
09 Sep 2008
First published
16 Oct 2008

Org. Biomol. Chem., 2008,6, 4399-4405

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Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C

T. Taniguchi, K. Monde, K. Nakanishi and N. Berova, Org. Biomol. Chem., 2008, 6, 4399 DOI: 10.1039/B813437E

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