Complete 1H NMR spectral fingerprint of huperzine A

Matthias Niemitz, Reino Laatikainen, Shao Nong Chen, Robert Kieps, Alan P. Kozikowski, Guido F. Pauli

Research output: Contribution to journalArticlepeer-review

Abstract

Complete analysis of the 1H NMR spectrum of huperzine A, 1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.02,7]trideca- 2(7),3,10-trien-5-one, a Lycopodium alkaloid and anti-Alzheimer drug lead containing an ABCD(E)(MN)(OP)X3Y3-type system of 15 nonexchangeable proton spins, is reported for the first time, and earlier assignments are corrected. The complete 1H parameter set of 11 chemical shifts clarifies the diastereotopism of both methylene groups, and provides a total of 38 observed H,H-couplings including 31 long-range ( 4-6J) connectivities. The NMR data is consistent with the comparatively rigid alicyclic backbone predicted by molecular mechanics calculations, and forms the basis for 1H NMR fingerprint analysis for the purpose of dereplication, purity analysis, and elucidation of structural analogs.

Original languageEnglish (US)
Pages (from-to)878-882
Number of pages5
JournalMagnetic Resonance in Chemistry
Volume45
Issue number10
DOIs
StatePublished - Oct 1 2007

Keywords

  • 15-spin system
  • Computerized analysis
  • Fingerprint
  • Hypercomplexity
  • Long-range couplings
  • NMR
  • Proton NMR

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)

Fingerprint

Dive into the research topics of 'Complete <sup>1</sup>H NMR spectral fingerprint of huperzine A'. Together they form a unique fingerprint.

Cite this