Enantiomeric Variability of Distaminolyne A. Refinement of ECD and NMR Methods for Determining Optical Purity of 1-Amino-2-Alkanols.

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Title

Enantiomeric Variability of Distaminolyne A. Refinement of ECD and NMR Methods for Determining Optical Purity of 1-Amino-2-Alkanols.

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ResearchSpace@Auckland

Description

Sample configurations of distaminolyne A (1a); isolated from the ascidians Pseudodistoma opacum and P. cereum, and collected at different sites in New Zealand, were investigated by two methods: Exciton coupled electronic circular dichroism (EC ECD) of the corresponding N,O-dibenzoyl derivative 1b; and chiral reagent derivatization of 1a with (S)- and (R)-α-methoxyphenylacetic acid (MPA), followed by ¹H-NMR analysis. Configuration and optical purity of 1a (%ee) was found to vary depending on t...

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Format

Research paper

Research format

Journal article

Date created

2018-12

Creator

Pearce, A Norrie / Copp, Brent R / Molinski, Tadeusz F

URL

https://hdl.handle.net/2292/62972

Related subjects

Alcohols / Alkenes / Biological Products / Circular Dichroism / Magnetic Resonance Spectroscopy / Acylation / Stereoisomerism / Geography / Models, Molecular / Optical Phenomena / absolute configuration / amino alcohols / marine natural products / Science & Technology / Life Sciences & Biomedicine / Physical Sciences / Biochemistry & Molecular Biology / Chemistry, Multidisciplinary / Chemistry / ABSOLUTE-CONFIGURATION / SPHINGOID BASES / AMINO ALCOHOL / SPONGE / BIOSYNTHESIS / ASSIGNMENT / 0304 Medicinal and Biomolecular Chemistry / 0305 Organic Chemistry / 0307 Theoretical and Computational Chemistry

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