Structure of argemonine. Identification as (−)-N-methylpavine

Martell, Michael J.; Soine, Taito O.; Kier, Lemont B.

doi:10.1002/jps.2600560811

Cited by 7 publications

(1 citation statement)

References 11 publications

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“…PbTNMT exhibited strict substrate specificity, only catalyzing the N ‐methylation of ( R , S )‐tetrahydropalmatine (133%) or ( R , S )‐stylopine (100%). The preference of TfPavNMT for (±)‐pavine (100%) as a substrate, resulting in formation of N ‐methylpavine (argemonine; Martell et al. , 1967), suggests TfPavNMT is a novel enzyme involved in pavine alkaloid metabolism.…”

Section: Resultsmentioning

confidence: 99%

Targeted metabolite and transcript profiling for elucidating enzyme function: isolation of novel N‐methyltransferases from three benzylisoquinoline alkaloid‐producing species

et al. 2009

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SUMMARYAn integrated approach using targeted metabolite profiles and modest EST libraries each containing approximately 3500 unigenes was developed in order to discover and functionally characterize novel genes involved in plant-specialized metabolism. EST databases have been established for benzylisoquinoline alkaloid-producing cell cultures of Eschscholzia californica, Papaver bracteatum and Thalictrum flavum, and are a rich repository of alkaloid biosynthetic genes. ESI-FTICR-MS and ESI-MS/MS analyses facilitated unambiguous identification and relative quantification of the alkaloids in each system. Manual integration of known and candidate biosynthetic genes in each EST library with benzylisoquinoline alkaloid biosynthetic networks assembled from empirical metabolite profiles allowed identification and functional characterization of four N-methyltransferases (NMTs). One cDNA from T. flavum encoded pavine N-methyltransferase (TfPavNMT), which showed a unique preference for (AE)-pavine and represents the first isolated enzyme involved in the pavine alkaloid branch pathway. Correlation of the occurrence of specific alkaloids, the complement of ESTs encoding known benzylisoquinoline alkaloid biosynthetic genes and the differential substrate range of characterized NMTs demonstrated the feasibility of bilaterally predicting enzyme function and species-dependent specialized metabolite profiles.

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Section: Resultsmentioning

confidence: 99%

Targeted metabolite and transcript profiling for elucidating enzyme function: isolation of novel N‐methyltransferases from three benzylisoquinoline alkaloid‐producing species

et al. 2009

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Benzomorphan related compounds. V. Synthesis of thienomorphans

Álvarez

Bosch

Cranados

et al. 1978

Journal of Heterocyclic Chem

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A series of thieno [2,3‐ƒ]‐, [3,2‐ƒ]‐ and [3,4‐ƒ]morphans prepared both by the Grewe synthesis and by the reaction of 2‐cyanopyridines with 3‐thienyllithium is described. Furthermore, a new synthetic route to thieno [2,3‐ƒ] morphans from 3‐ketotetrahydrolhiophene is reported. Separation and assignment of the α‐ and β‐diastereomerie structures by means of nmr data is reported. Some side products were isolated and their structures were confirmed on the basis of their spectral data. Mechanisms for their formation are proposed.

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Synthesis of (±)-Norargemonine

Lee

Soine

1968

Journal of Pharmaceutical Sciences

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Structure of argemonine. Identification as (−)-N-methylpavine

Cited by 7 publications

References 11 publications

Targeted metabolite and transcript profiling for elucidating enzyme function: isolation of novel N‐methyltransferases from three benzylisoquinoline alkaloid‐producing species

Targeted metabolite and transcript profiling for elucidating enzyme function: isolation of novel N‐methyltransferases from three benzylisoquinoline alkaloid‐producing species

Benzomorphan related compounds. V. Synthesis of thienomorphans

Synthesis of (±)-Norargemonine

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