On the biosynthetic pathway of papaverine via (S)-reticuline theoretical vs. experimental study.
Nat Prod Commun
; 7(5): 581-6, 2012 May.
Article
in En
| MEDLINE
| ID: mdl-22799080
The electronic structures, optical properties and molecular structures of a series of isoquinoline alkaloids resulting in the formation of papaverine, through a proposed biosynthetic pathway via S(+)-reticuline were elucidated. The mechanism of papaverine synthesis was studied by electronic absorption, diffuse reflectance, fluorescence and CD spectroscopy, as well as ESI and MALDI Orbitrap imaging mass spectrometry. Quantum chemical DFT calculations in the gas phase and solution were performed with a view to study the electronic transitions of the interacting species, corresponding proposed intermediates, and the expected mass spectrometric fragments. The complete study and understanding of the mechanism of the biosynthetic pathway in the poppy plants appears important for the functional oriented drug-design and synthesis of corresponding structurally related alkaloids.
Search on Google
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Papaver
/
Papaverine
/
Benzylisoquinolines
Language:
En
Journal:
Nat Prod Commun
Journal subject:
BOTANICA
/
FARMACOLOGIA
/
QUIMICA
Year:
2012
Document type:
Article
Affiliation country:
Germany
Country of publication:
United States