scholarly journals Biosynthesis of isoprenoids (carotenoids, sterols, prenyl side-chains of chlorophylls and plastoquinone) via a novel pyruvate/glyceraldehyde 3-phosphate non-mevalonate pathway in the green alga Scenedesmus obliquus*

1996 ◽  
Vol 316 (1) ◽  
pp. 73-80 ◽  
Author(s):  
Jörg SCHWENDER ◽  
Myriam SEEMANN ◽  
Hartmut K. LICHTENTHALER ◽  
Michel ROHMER
Keyword(s):  
Green Alga ◽  
13C Nmr ◽  
Mevalonate Pathway ◽  
Scenedesmus Obliquus ◽  
13C Nmr Spectroscopy ◽  
Side Chains ◽  
Isopentenyl Diphosphate ◽  
The Novel ◽  
13C Labelling ◽  
Β Carotene

Isoprenoid biosynthesis was investigated in the green alga Scenedesmus obliquus grown heterotrophically on 13C-labelled glucose and acetate. Several isoprenoid compounds were isolated and investigated by 13C-NMR spectroscopy. According to the 13C-labelling pattern indicated by the 13C-NMR spectra, the biosynthesis of all plastidic isoprenoids investigated (prenyl side-chains of chlorophylls and plastoquinone-9, and the carotenoids β-carotene and lutein), as well as of the non-plastidic cytoplasmic sterols, does not proceed via the classical acetate/mevalonate pathway (which leads from acetyl-CoA via mevalonate to isopentenyl diphosphate), but via the novel glyceraldehyde 3-phosphate/pyruvate route recently detected in eubacteria. Formation of isopentenyl diphosphate involves the condensation of a C2 unit derived from pyruvate decarboxylation with glyceraldehyde 3-phosphate and a transposition yielding the branched C5 skeleton of isoprenic units.

scholarly journals Determination of C-23 Configuration in (20R)-23-Hydroxycholestane Side Chain of Steroid Compounds by 1H and 13C NMR Spectroscopy

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Alla A. Kicha ◽  
Anatoly I. Kalinovsky ◽  
Alexander S. Antonov ◽  
Oleg S. Radchenko ◽  
Natalia V. Ivanchina ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
13C Nmr ◽  
13C Nmr Spectroscopy ◽  
Side Chain ◽  
Side Chains ◽  
Model Compounds ◽  
1H And 13C Nmr ◽  
C 23 ◽  
C Nmr

Epimeric (20 R,23 R)- and (20 R,23 S)-23-hydroxycholestane steroids were synthesized. Their structures were elucidated by extensive 1H and 13C NMR spectroscopy and application of the Mosher's method. All proton and carbon signals of the side chains were assigned. Based on these assignments spectral data allow the determination of the C-23 stereochemistry of (20 R)-23-hydroxycholestane side chains of the new natural steroids by comparison with spectra of the obtained model compounds. As a result, the C-23 configuration of two steroid compounds from the starfishes Lethasterias nanimensis chelifera and Lethasterias fusca was established.

scholarly journals Biosynthesis of the labdane diterpene marrubiin in Marrubium vulgare via a non-mevalonate pathway

1997 ◽  
Vol 326 (2) ◽  
pp. 449-454 ◽  
Author(s):  
Werner KNÖSS ◽  
Bernd REUTER ◽  
Josef ZAPP
Keyword(s):  
Mevalonate Pathway ◽  
Alternative Pathway ◽  
Mevalonic Acid ◽  
13C Nmr Spectroscopy ◽  
Shoot Cultures ◽  
Isopentenyl Diphosphate ◽  
Glucose Incorporation ◽  
Labdane Diterpene ◽  
Marrubium Vulgare ◽  
Putative Precursor

The biosynthesis of the furanic labdane diterpene marrubiin has been studied in plantlets and shoot cultures of Marrubium vulgare(Lamiaceae). The use of [2-14C]acetate, [2-14C]pyruvate, [2-14C]mevalonic acid and [U-14C]glucose incorporation experiments showed that the labelling of sterols in etiolated shoot cultures of M. vulgare was in accordance with their biosynthesis via the acetate–mevalonate pathway. In contrast, the incorporation rates of these precursors into the diterpene marrubiin could not be explained by biosynthesis of this compound via the acetate–mevalonate pathway. Cultivation of etiolated shoot cultures of M. vulgare on medium containing [1-13C]glucose and subsequent 13C-NMR spectroscopy of marrubiin led to the conclusion that the biosynthesis of marrubiin follows a non-mevalonate pathway. All isoprenic units of 13C-labelled marrubiin were enriched in those carbons that correspond to positions 1 and 5 of a putative precursor isopentenyl diphosphate. This labelling pattern from [1-13C]glucose is consistent with an alternative pathway via trioses, which has already been shown to occur in Eubacteria and Gymnospermae. The labdane skeleton is a precursor of many other skeletal types of diterpenes. Therefore it becomes obvious that in connection with the few known examples of a non-mevalonate pathway to isoprenoids the formation of some isoprenoids in plants via a non-mevalonate pathway might be quite common.

Non-mevalonate isoprenoid biosynthesis: enzymes, genes and inhibitors

2000 ◽  
Vol 28 (6) ◽  
pp. 785-789 ◽  
Author(s):  
H. K. Lichtenthaler
Keyword(s):  
Malaria Parasite ◽  
Pathogenic Bacteria ◽  
Mevalonate Pathway ◽  
Isoprenoid Biosynthesis ◽  
Mep Pathway ◽  
Isopentenyl Diphosphate ◽  
The Novel ◽  
Isoprenoid Pathway

The essential steps of the novel non-mevalonate pathway of isopentenyl diphosphate and isoprenoid biosynthesis in plants are described. The first five enzymes and genes of this 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) pathway are known. The herbicide fosmidomycin specifically blocks the second enzyme, the DOXP reductoisomerase. The DOXP/MEP pathway is also present in several pathogenic bacteria and the malaria parasite. Hence, all herbicides and inhibitors blocking this novel isoprenoid pathway in plants are also potential drugs against malaria and diseases caused by pathogenic bacteria.

scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Conjugate Addition ◽  
13C Nmr Spectroscopy ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Esi Mass Spectrometry ◽  
The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

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