The prediction of isotopic patterns in phenylpropanoids from their precursors and the mechanism of the NIH-shift: Basis of the isotopic characteristics of natural aromatic compounds

• Published in: Phytochemistry (Oxford) Vol. 67; no. 11; pp. 1094 - 1103
• Main Authors: Schmidt, Hanns-Ludwig, Werner, Roland A., Eisenreich, Wolfgang, Fuganti, Claudio, Fronza, Giovanni, Remaud, Gérald, Robins, Richard J.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier Ltd 01.06.2006; Elsevier
• Subjects: 13C-Pattern; 2H-Pattern; aromatic compounds; Benzaldehydes - chemistry; Benzene Derivatives - chemistry; Biological and medical sciences; Biological Factors - chemistry; carbon; Carbon Isotopes; Chemical constitution; Cinnamates - chemistry; Coumarins - chemistry; deuterium; Deuterium - chemistry; Fundamental and applied biological sciences. Psychology; Hydroxylation; Isotope effects; Magnetic Resonance Spectroscopy; Models, Chemical; NADP - chemistry; Natural aromatic compounds; NIH-Shift; phenylpropanoids; Phosphoenolpyruvate - chemistry; Plant physiology and development; Propanols - chemistry; Salicylates - chemistry; shikimate pathway; Shikimic Acid - chemistry; Shikimic acid pathway; stable isotopes; Sugar Phosphates - chemistry; vanillin; Shikimic acid pathway; 13C-Pattern; 2H-Pattern; Isotope effects; Natural aromatic compounds; NIH-Shift; Molecular structure; Biosynthesis; Metabolism; 13C-Pattem; Coumarin; Precursor; Shikimic acid; Aromatic compound; Vanillin; Cinnamic acid(hydroxy)

The deuterium patterns (the relative abundances of isotopomers) of natural aromatic compounds are determined by that of their precursors in the shikimic acid pathway – erythrose, PEP and NADPH – and by intramolecular (IIE) and kinetic (KIE) isotope effects accompanying the NIH-shift during hydroxyla...