Stereochemical Study of Sphingosine by Vibrational Circular Dichroism.

Org Lett

Faculty of Advanced Life Science, Frontier Research Center for the Post-Genome Science and Technology, Hokkaido University, Kita 21, Nishi 11, Sapporo 001-0021, Japan.

Published: May 2016

Vibrational circular dichroism (VCD) was first applied to the stereochemical analysis of sphingosine. VCD patterns derived from the C═C stretch as well as other mid-infrared (IR) regions were practical markers to discriminate all the stereoisomers of intact sphingosine. Glutaraldehyde was found as an excellent derivatizing reagent for sphingosine which improves its solubility in VCD-friendly nonpolar solvents such as chloroform and enhances the VCD intensities by forming a rigid cyclized structure.

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http://dx.doi.org/10.1021/acs.orglett.6b00477DOI Listing

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