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Long-range 1H-15N two-dimensional heteronuclear shift correlation of the alkaloid vincamine at natural abundance

✍ Scribed by Gary E. Martin


Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
289 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

Long‐range ^1^H‐^15^N heteronuclear correlation pathways in the alkaloid vincamine, a structural constituent or biogenetic congener of numerous Vinca alkaloids, are reported. Correlations were observed through the use of the GHNMQC (Gradient‐enhanced Hydrogen‐Nitrogen Multiple Quantum Coherence) 2D nmr experiment at natural abundance. An unanticipated four‐bond coupling between the H15a resonance and N4 was observed in contrast to the typical two‐ and three‐bond coupling pathways. Nitrogen‐15 chemical shift comparisons are drawn between vincamine and structurally related alkaloids including ajmaline and the velbanamine portion of the semi‐synthetic alkaloid vinorelbine (Navelbine^TM^).


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