An Acetylenic Lipid from the New Zealand Ascidian Pseudodistoma cereum: Exemplification of an Improved Workflow for Determination of Absolute Configuration of Long-Chain 2-Amino-3-alkanols

J Nat Prod. 2019 Aug 23;82(8):2291-2298. doi: 10.1021/acs.jnatprod.9b00504. Epub 2019 Jul 29.

Abstract

An acetylenic 2-amino-3-alcohol, distaminolyne B (2), isolated from the New Zealand ascidian Pseudodistoma cereum, is reported. The isolation and structure elucidation of 2 and assignment of 2S,3S absolute configuration (AC) using the exciton coupled circular dichroism technique are described. Using a methodologically facile workflow, the same AC was also established by analysis of specific rotation, terminal methyl C-1 δC chemical shift, and NH δH and J values of the N,O-diacetate derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / chemistry*
  • Alkaloids
  • Alkenes / chemistry*
  • Animals
  • Humans
  • Lipids / chemistry*
  • Urochordata / chemistry*

Substances

  • Alkaloids
  • Alkenes
  • Lipids
  • Acetylene