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  18O pattern and biosynthesis of natural plant products

Schmidt, H.-L., Werner, R. A., & Roßmann, A. (2001). 18O pattern and biosynthesis of natural plant products. Phytochemistry, 58(1), 9-32.

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BGC0410.pdf (Publisher version), 491KB
 
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Schmidt, H.-L., Author
Werner, R. A.1, Author           
Roßmann, A., Author
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1Service Facility Stable Isotope/Gas Analytics, Dr. W. A. Brand, Max Planck Institute for Biogeochemistry, Max Planck Society, ou_1497772              

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Free keywords: delta O-18 value; O-18 abundance; O-18 pattern; kinetic isotope effect; equilibrium isotope effect; biosynthesis; mechanism of enzyme catalysed reactions; natural compounds; carbohydrates; phenylpropanes; isoprenoids; alkaloids; acids; alcohols; esters; carbonyl compounds Oxygen-isotope fractionation; tree-ring cellulose; atmospheric oxygen; carbon-dioxide; ratio analysis; online determination; chemical mechanism; orange juice; c-3 plants; water
 Abstract: Oxygen atoms in plant products originate from CO2, H2O and O-2, precursors with quite different delta O-18 values. Furthermore their incorporation by different reactions implies isotope effects. On this base the resulting non-statistical O-18 distributions in natural compounds are discussed. The delta O- 18 value of cellulose is correlated to that of the leaf water, and the observed O-18 enrichment (similar to + 27 parts per thousand) is generally attributed to an equilibrium isotope effect between carbonyl groups and water. However, as soluble and heterotrophically synthezised carbohydrates show other correlations, a non-statistical O-18 distribution - originating from individual biosynthetic reactions - is postulated for carbohydrates. Similarly, the delta O-18 values of organic acids, carbonyl compounds, alcohols and esters indicate water- correlated, but individual O-18 abundances (e.g. O from acyl groups similar to + 19% above water), depending upon origin and biosyntheses. Alcoholic groups introduced by monooxygenase reactions, e.g. in sterols and phenols, show delta O-18 values near + 5 parts per thousand, in agreement with an assumed isotope fractionation factor of similar to1.02 on the reaction with atmospheric oxygen (delta O-18 = +23.5 parts per thousand). Correspondingly, a "thermodynamically ordered isotope distribution" is only observed for oxygen in some functional groups correlated to an origin from CO2 and H2O, not from O-2. The individual isotopic increments of functional groups permit the prediction of global delta O-18 values of natural compounds on the basis of their biosynthesis. (C) 2001 Published by Elsevier Science Ltd.

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 Dates: 2001
 Publication Status: Issued
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 Identifiers: Other: BGC0410
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Title: Phytochemistry
Source Genre: Journal
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Publ. Info: Oxford : Pergamon
Pages: - Volume / Issue: 58 (1) Sequence Number: - Start / End Page: 9 - 32 Identifier: CoNE: https://pure.mpg.de/cone/journals/resource/954925433416
ISSN: 0031-9422