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Topic: Dimethylallyl pyrophosphate

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	Kevin Ahern's Notes
		Isoprene - 5 carbon units - 1) isopentenyl pyrophosphate and dimethylallyl pyrophosphate.
		Reaction of isopentenyl pyrophospahte with dimethylallyl pyrophosphate yields a 10-carbon intermediate, geranyl pyrophosphate
		Reaction of geranyl pyrophosphate with isopentenyl pyrophosphate yields a 15 carbon intermediate - farnesyl pyrophosphate.
	oregonstate.edu /dept/biochem/hhmi/hhmiclasses/bb451/lectnoteskga/highlightsstermetab.html (520 words)

	Cholesterol Synthesis
		Pyrophosphomevolanate Decarboxylase catalyzes ATP-dependent decarboxylation, with dehydration, to yield
		catalyzes head-to-head condensation of 2 molecules of farnesyl pyrophosphate, with reduction by NADPH, to yield
		: Degradation of HMG-CoA Reductase is stimulated by cholesterol, by oxidized derivatives of cholesterol, by mevalonate, and by farnesol (dephosphorylated farnesyl pyrophosphate).
	www.rpi.edu /dept/bcbp/molbiochem/MBWeb/mb2/part1/cholesterol.htm (1044 words)

	Lipid2 (Site not responding. Last check: 2007-10-26)
		Isopentenyl pyrophosphate is equilibrated with dimethylallyl pyrophosphate in an enzyme catalyzed isomerization.
		Dimethylallyl pyrophosphate is set up for an SN1 type reaction, but only in the active site of an enzyme which can cancel the charges on the pyrophosphate group.
		Neutral pyrophosphate is a good leaving group, but pyrophosphate will normally be ionized in neutral solution, and the anion is a poor leaving group.
	instruct.uwo.ca /chemistry/223b-98/lipid2.htm (1684 words)

	LIPIDS: EXERCISES (Site not responding. Last check: 2007-10-26)
		Sketch the mechanism for the conversion of isopentenyl pyrophosphate to geranyl pyrophosphate.
		Sketch the mechanism for the conversion of geranyl pyrophosphate (GPP) to limonene.
		Sketch the mechanism for the conversion of GPP to farnesyl pyrophosphate (FPP).
	research.cm.utexas.edu /nbauld/ch25exercises/lipids.html (280 words)

	Saccharomyces cerevisiae pyrophosphate
		Coenzyme A + acetate + ATP = acetyl-CoA + pyrophosphate + AMP
		L-aspartate + citrulline + ATP = L-arginino-succinate + pyrophosphate + AMP
		β-alanine + pantoate + ATP = pantothenate + pyrophosphate + AMP,
	pathway.yeastgenome.org:8555 /YEAST/NEW-IMAGE?type=COMPOUND&object=PPI (357 words)

	Synthesis of Cholesterol
		Head to tail condensation of Isopentyl pyrophosphate and Dimethylallyl pyrophosphate forms a 10 carbon chain which elimination of 1 pyrophosphate.
		A different head to tail condensation of geranyl pyrophosphate with isopentenyl pyrophosphate gives a 15 carbon intermediate which is this time called a Farnesyl pyrophosphate.
		Head to head joining of two molecules of Farnesyl pyrophosphate and elimination of 2 pyrophosphate groups gives a 30 carbon chain which is called a Squalene.
	www.aci.k12.tr /prochem/proj8/synthesis_of_cholesterol.htm (296 words)

	Professional Solutions: Herb Med Pro
		Cell-free homogenates from sage (Salvia officinalis) leaves convert dimethylallyl pyrophosphate and isopentenyl pyrophosphate to a mixture of geranyl pyrophosphate, farnesyl pyrophosphate, and geranylgeranyl pyrophosphate, with farnesyl pyrophosphate predominating.
		Enzymes from Salvia officinalis and Tanacetum vulgare leaf epidermis catalyze the conversion of the acyclic precursor geranyl pyrophosphate to the cyclic monoterpenes (+)- and (-)-bornyl pyrophosphate, respectively.
		Enzymes from Salvia officinalis capable of catalyzing the isomerization and subsequent cyclization of geranyl pyrophosphate to the monoterpenes (+)-alpha-pinene and (+)-bornyl pyrophosphate were examined with the noncyclizable substrate analog 6,7-dihydrogeranyl pyrophosphate.
	www.gaiaherbs.com /herbs.php?BaseDir=/herbs.php&GET=/HerbTemplates/subcategory.asp?varSubcategory_ID=30&varHerb_ID=194 (905 words)

	[No title] (Site not responding. Last check: 2007-10-26)
		It is thought that the same prenyl transferase catalyzes all the steps from dimethylallyl pyrophosphate to geranylgeranyl pyrophosphate (444; R.W. Harding, personal communication), and it has been proposed that a separate prenyl transferase converts dimethylallyl pyrophosphate to farnesyl pyrophosphate for sterol synthesis (445).
		al-2 is reported blocked between geranylgeranyl pyrophosphate and phytoene (445) and between prephytoene pyrophosphate and phytoene (572).
		al-3 is alternately reported blocked between isopentenyl pyrophosphate and geranylgeranyl pyrophosphate (445) and between prephytoene pyrophosphate and phytoene (572), but it is not blocked in the production of farnesyl pyrophosphate or sterols (398, 445).
	www.fgsc.net /compend/fig9.html (217 words)

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