Complete 1H NMR spectral fingerprint of huperzine A

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

doi:10.1002/mrc.2061

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 journal › Article › peer-review

17 Scopus citations

Abstract

Complete analysis of the ¹H NMR spectrum of huperzine A, 1-amino-13-ethylidene-11-methyl-6-aza-tricyclo[7.3.1.0^2,7]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 language	English (US)
Pages (from-to)	878-882
Number of pages	5
Journal	Magnetic Resonance in Chemistry
Volume	45
Issue number	10
DOIs	https://doi.org/10.1002/mrc.2061
State	Published - Oct 2007
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

General Chemistry
General Materials Science

Access to Document

10.1002/mrc.2061

Cite this

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title = "Complete 1H NMR spectral fingerprint of huperzine A",

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.",

keywords = "15-spin system, Computerized analysis, Fingerprint, Hypercomplexity, Long-range couplings, NMR, Proton NMR",

author = "Matthias Niemitz and Reino Laatikainen and Chen, {Shao Nong} and Robert Kieps and Kozikowski, {Alan P.} and Pauli, {Guido F.}",

year = "2007",

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doi = "10.1002/mrc.2061",

language = "English (US)",

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journal = "Magnetic Resonance in Chemistry",

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AU - Niemitz, Matthias

AU - Laatikainen, Reino

AU - Chen, Shao Nong

AU - Kieps, Robert

AU - Kozikowski, Alan P.

AU - Pauli, Guido F.

PY - 2007/10

Y1 - 2007/10

N2 - 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.

AB - 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.

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KW - Hypercomplexity

KW - Long-range couplings

KW - NMR

KW - Proton NMR

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