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The steroids and sterols in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to proteins, e.g., to enhance their attachment to the cell membrane; this is known as isoprenylation.
The term terpene was coined in 1866 by the German chemist August Kekulé to denote all hydrocarbons having the empirical formula C 10 H 16, of which camphene was one. Previously, many hydrocarbons having the empirical formula C 10 H 16 had been called "camphene", but many other hydrocarbons of the same composition had different names.
Biogenetic precursor of all indole alkaloids is the amino acid tryptophan. For most of them, the first synthesis step is decarboxylation of tryptophan to form tryptamine. Dimethyltryptamine (DMT) is formed from tryptamine by methylation with the participation of coenzyme of S-adenosyl methionine (SAM).
Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is the precursor to all sesquiterpenes, which comprises thousand of compounds. [1] These include all sesquiterpenes as well as sterols and carotenoids . [ 2 ]
Geranyl pyrophosphate is the precursor to monoterpenes (and hence monoterpenoids). [2] Elimination of the pyrophosphate group from geranyl pyrophosphate leads to the formation of acyclic monoterpenes such as ocimene and the myrcenes. Hydrolysis of the phosphate groups leads to the prototypical acyclic monoterpenoid geraniol.
By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The terms triterpene and triterpenoid often are used interchangeably. Triterpenoids possess a rich chemistry and pharmacology (e.g. cholesterol ) with several pentacyclic motifs.
Gossypol is a terpenoid aldehyde which is formed metabolically through acetate via the isoprenoid pathway. [10] The sesquiterpene dimer undergoes a radical coupling reaction to form gossypol. [ 11 ] The biosynthesis begins when geranyl pyrophosphate (GPP) and isopentenyl pyrophosphate (IPP) are combined to make the sesquiterpene precursor ...
The isoprene skeleton can be found in naturally occurring compounds called terpenes and terpenoid (oxygenated terpenes), collectively called isoprenoids. These compounds do not arise from isoprene itself. Instead, the precursor to isoprene units in biological systems is dimethylallyl pyrophosphate (DMAPP) and its isomer isopentenyl ...