Unreferenced stub auto yes date December 2009 Chembox verifiedrevid 424660305 ImageFile Farnesyl pyrophosphate.png ImageSize 220px ImageName Skeletal formula ImageFile1 Farnesylpyrophosphate 3D balls.png ImageSize1 250px ImageName1 Ball and stick model IUPACName OtherNames Section1 Chembox Identifiers CASNo Ref cascite correct ?? CASNo 13058 04 3 PubChem 706 SMILES MeSHName farnesylpyrophosphate Section2 Chembox Properties Formula C sub 15 sub H sub 28 sub O sub 7 sub P sub 2 sub MolarMass 382.326 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Farnesylpyrophosphate FPP , also known as farnesyl diphosphate FDP , is an intermediate in the HMG CoA reductase pathway used by organisms in the biosynthesis of terpene s, terpenoid s, and sterol s. It is the immediate precursor of squalene via the enzyme squalene synthase , dehydrodolichol diphosphate a precursor of dolichol , and geranylgeranyl pyrophosphate GGPP . Biosynthesis Farnesylpyrophosphate synthase a prenyl transferase catalyzes sequential condensation reactions of dimethylallyl pyrophosphate with 2 units of 3 isopentenyl pyrophosphate to form farnesylpyrophosphate, as is shown in the following two steps Dimethylallyl pyrophosphate reacts with 3 isopentenyl pyrophosphate to form geranyl pyrophosphate Image Cholesterol Synthesis Reaction8.png Geranyl pyrophosphate then reacts with another molecule of 3 isopentenyl pyrophosphate to form farnesylpyrophosphate Image Cholesterol Synthesis Reaction9.png Regulation The above reactions are inhibited by bisphosphonate s used for osteoporosis . Related compounds Farnesene Farnesol Geranyl pyrophosphate Geranylgeranyl pyrophosphate Cholesterol metabolism intermediates DEFAULTSORT FarnesylPyrophosphate Category Organophosphates Category Sesquiterpenes Biochem stub fi Farnesyylipyrofosfaatti zh ... more details
Chembox verifiedrevid 444077628 ImageFile Pyrophosphate anion.png ImageSize 150px ImageFile1 Pyrophosphate 3D balls.png ImageSize1 150px ImageAlt1 ImageName1 Pyrophosphate anion IUPACName OtherNames Diphosphate Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 559142 InChI 1 H4O7P2 c1 8 2,3 7 9 4,5 6 h H2,1,2,3 H2,4,5,6 p 4 InChIKey XPPKVPWEQAFLFU XBHQNQODAI StdInChI Ref stdinchicite correct chemspider StdInChI 1S H4O7P2 c1 8 2,3 7 9 4,5 6 h H2,1,2,3 H2,4,5,6 p 4 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey XPPKVPWEQAFLFU UHFFFAOYSA J CASNo ... . Pyrophosphates are good complexing agents and have many uses in industrial chemistry. Pyrophosphate is the first member of an entire series of polyphosphate s. The term pyrophosphate is also the name ... with inorganic phosphate as for dimethylallyl pyrophosphate . This bond is also referred to as a high energy phosphate bond. The synthesis of tetraethyl pyrophosphate was first described in 1854 ..., when a nucleotide is incorporated into a growing DNA or RNA strand by a polymerase , pyrophosphate ... pyrophosphate reacts with the 3 nucleotidemonophosphate NMP or dNMP , which is removed from the oligonucleotide to release the corresponding triphosphate dNTP from DNA, or NTP from RNA . The pyrophosphate ... reactions of simple polyphosphates such as pyrophosphate, linear triphosphate, Adenosine diphosphate ... cite journal author Huebner PWA, Milburn RM title Hydrolysis of pyrophosphate to orthophosphate ... Bone Calcium pyrophosphate Calcium pyrophosphate dihydrate deposition disease Catalysis DNA High energy ... monophosphate RNA Sodium pyrophosphate Structural phosphate Superphosphate Thiamine pyrophosphate Tooth Zinc pyrophosphate Div col end References reflist 2 Further reading cite journal author Schr der ... bcm 0296.pdf External links Wiktionary diphosphate pyrophosphate MeshName Pyrophosphates footer templates ... fr Pyrophosphate gl Pirofosfato it Pirofosfato hu Difoszf tok nl Pyrofosfaat pl Pirofosforany ... more details
Chembox Watchedfields changed verifiedrevid 443835762 ImageFile Geranylgeranyl pyrophosphate.png ImageSize IUPACName OtherNames Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 394418 InChI 1 C20H36O7P2 c1 17 2 9 6 10 18 3 11 7 12 19 4 13 8 14 20 5 15 16 26 29 24,25 27 28 21,22 23 h9,11,13,15H,6 8,10,12,14,16H2,1 5H3, H,24,25 H2,21,22,23 b18 11 ,19 13 ,20 15 InChIKey OINNEUNVOZHBOX QIRCYJPOBR StdInChI Ref stdinchicite correct chemspider StdInChI 1S C20H36O7P2 c1 17 2 9 6 10 18 3 11 7 12 19 4 13 8 14 20 5 15 16 26 29 24,25 27 28 21,22 23 h9,11,13,15H,6 8,10,12,14,16H2,1 5H3, H,24,25 H2,21,22,23 b18 11 ,19 13 ,20 15 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey OINNEUNVOZHBOX QIRCYJPOSA N CASNo 6699 20 3 PubChem 447277 ChEBI Ref ebicite correct EBI ChEBI 48861 SMILES O P O O OP O O OC C C CC C C C CC C C C CC C C C C C MeSHName geranylgeranyl pyrophosphate Section2 Chembox Properties C 20 H 36 O 7 P 2 Appearance Density MeltingPt BoilingPt Section3 Chembox Hazards Solubility MainHazards FlashPt Autoignition Geranylgeranyl pyrophosphate is an intermediate in the HMG CoA reductase pathway used by organisms in the biosynthesis of terpene s and terpenoid s. ref http www.rpi.edu dept bcbp molbiochem MBWeb mb2 part1 cholesterol.htm Cholesterol Synthesis , Rensselaer Polytechnic Institute ref In plants it is also the precursor to carotenoid s, gibberellin s, tocopherol s, and chlorophyll s. It is also a precursor to geranylgeranylation geranylgeranylated proteins. Related compounds Geranylgeraniol Geranyl pyrophosphate Farnesyl pyrophosphate References reflist Cholesterol metabolism intermediates DEFAULTSORT Geranylgeranyl Pyrophosphate Category Organophosphates Category Diterpenes Biochem stub ja fi Geranyyligeranyylipyrofosfaatti ... more details
chembox verifiedrevid 403176984 ImageFile undecaprenyl pyrophosphate.png ImageSize 280px ImageName Skeletal formula of C55 isoprenyl pyrophosphate ImageFile1 C55 isoprenyl pyrophosphate 3D balls.png ImageSize1 280px ImageName1 Ball and stick model of C55 isoprenyl pyrophosphate IUPACName phosphono 2 E ,6 E ,10 E ,14 E ,18 E ,22 E ,26 E ,30 E ,34 E ,38 E 3,7,11,15,19,23,27,31,35,39,43 undecamethyltetratetraconta 2,6,10,14,18,22,26,30,34,38,42 undecaenyl hydrogen phosphate IUPACName hidden yes OtherNames C55 undecaprenyl pyrophosphate Undecaprenyl pyrophosphate Pyrophosphoryl undecaprenol Undecaisoprenyl pyrophosphate Undecaprenyl diphosphate Section1 Chembox Identifiers CASNo 31867 59 1 PubChem 5280604 SMILES CC CCC C C CC C C CC C C CC C C CC C C CC C C CC C C CC C C CC C C CC C C COP O O OP O O O C C C C C C C C C C C Section2 Chembox Properties C 55 H 92 O 7 P 2 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition C55 isoprenyl pyrophosphate undecaprenyl pyrophosphate is an essential molecule involved in construction of the bacterial peptidoglycan cell wall . organic compound stub microbiology stub Category Organophosphates Category Terpenes and terpenoids ... more details
food s containing sodium pyrophosphate include chicken nugget s, marshmallows , pudding , crab ... common baking powder s. In toothpaste and dental floss, sodium pyrophosphate acts as a Calculus ... them from being deposited on teeth . Sodium pyrophosphate is sometimes used in household detergent ... of water , promoting algae growth. Calcium pyrophosphate is the crystal deposited in joints in the medical ... de Tetranatriumdiphosphat fr Pyrophosphate de sodium it Pirofosfato di sodio pt Pirofosfato ... more details
chembox verifiedrevid 451189391 ImageFile IPP.png ImageSize 210px ImageName Skeletal formula of IPP ImageFile1 Isopentenyl pyrophosphate 3D balls.png ImageSize1 220px ImageName1 Ball and stick model of IPP IUPACName hydroxy 3 methylbut 3 enoxy phosphoryl oxyphosphonic acid OtherNames Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 13115335 InChI 1 C5H12O7P2 c1 5 2 3 4 11 14 9,10 12 13 6,7 8 h1,3 4H2,2H3, H,9,10 H2,6,7,8 p 3 InChIKey NUHSROFQTUXZQQ DFZHHIFOAI StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H12O7P2 c1 5 2 3 4 11 14 9,10 12 13 6,7 8 h1,3 4H2,2H3, H,9,10 H2,6,7,8 p 3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey NUHSROFQTUXZQQ UHFFFAOYSA K CASNo Ref cascite correct ?? CASNo 358 71 4 PubChem 15983957 ChEBI Ref ebicite correct EBI ChEBI 128769 SMILES CC C CCOP O O OP O O O MeSHName isopentenyl pyrophosphate Section2 Chembox Properties Formula C sub 5 sub H sub 12 sub O sub 7 sub P sub 2 sub MolarMass 246.092 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Isopentenyl pyrophosphate IPP is an intermediate in the classical, HMG CoA reductase pathway used by organisms in the biosynthesis of terpene s and terpenoid s. IPP is formed from acetyl CoA via mevalonic acid . IPP can then be isomerized to dimethylallyl pyrophosphate by the enzyme isopentenyl pyrophosphate isomerase . Image Mevalonate pathway.png 350px thumb center Mevalonate pathway Image Sterol synthesis.svg thumb center 350px Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate IPP , dimethylallyl pyrophosphate DMAPP , geranyl pyrophosphate GPP and squalene shown. Some intermediates are omitted. IPP can be synthesized via the alternative, non mevalonate pathway of isoprenoid biosynthesis instead, where it is formed from E 4 hydroxy 3 methyl but 2 enyl pyrophosphate HMB PP by the enzyme HMB PP reductase LytB, IspH . The non m ... more details
Unreferenced stub auto yes date December 2009 Chembox verifiedrevid 443496302 ImageFile calcium pyrophosphate.png ImageSize 200px IUPACName Calcium diphosphate OtherNames Diphosphoric acid, calcium salt 1 2 Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 23034 UNII Ref fdacite correct FDA UNII X69NU20D19 InChI 1 2Ca.H4O7P2 c 1 8 2,3 7 9 4,5 6 h H2,1,2,3 H2,4,5,6 q2 2 p 4 InChIKey JUNWLZAGQLJVLR XBHQNQODAN StdInChI Ref stdinchicite correct chemspider StdInChI 1S 2Ca.H4O7P2 c 1 8 2,3 7 9 4,5 6 h H2,1,2,3 H2,4,5,6 q2 2 p 4 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey JUNWLZAGQLJVLR UHFFFAOYSA J CASNo 7790 76 3 CASNo Ref cascite correct CAS PubChem 24632 ChEBI Ref ebicite correct EBI ChEBI 32598 SMILES Ca 2 . Ca 2 . O P O O OP O O O MeSHName Calcium pyrophosphate Section2 Chembox Properties Formula Ca sub 2 sub O sub 7 sub P sub 2 sub MolarMass 254.053 g mol Appearance Density 3.09 g cm sup 3 sup MeltingPt 1230 C BoilingPt Solubility insoluble Section3 Chembox Hazards EUIndex Not listed NFPA H 2 NFPA F 0 NFPA R 0 NFPA O FlashPt Non flammable Section8 Chembox Related OtherAnions Calcium phosphate OtherCations Magnesium pyrophosphate br Sodium pyrophosphate Calcium pyrophosphate Ca sub 2 sub O sub 7 sub P sub 2 sub is a chemical compound that can be formed by the reaction of pyrophosphoric acid and a calcium base or by strongly heating calcium phosphate or calcium ammonium phosphate. It is commonly used as a mild abrasive agent in toothpastes . Deposition of CPPD in articular joints causes an arthritis condition called pseudogout . See also Calcium pyrophosphate deposition disease Calcium compounds DEFAULTSORT Calcium Pyrophosphate Category Calcium compounds Category Pyrophosphates Inorganic compound stub ar ja sr Kalcijum pirofosfat zh ... more details
chembox verifiedrevid 402890942 Name Zinc pyrophosphate Reference ref name hand Citation last Lide first David R. author link last2 first2 author2 link publication date date year 1998 title Handbook of Chemistry and Physics edition 87 volume series publication place Boca Raton, FL place publisher CRC Press id isbn 0 8493 0594 2 doi oclc pages 4 96 url accessdate ref ImageFile Zinc pyrophosphate.png ImageSize ImageName Zinc pyrophosphate OtherNames Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 56393 PubChem 62641 InChI 1 H4O7P2.2Zn c1 8 2,3 7 9 4,5 6 h H2,1,2,3 H2,4,5,6 q 2 2 p 4 InChIKey OMSYGYSPFZQFFP XBHQNQODAA SMILES Zn 2 . Zn 2 . O P O O OP O O O StdInChI Ref stdinchicite correct chemspider StdInChI 1S H4O7P2.2Zn c1 8 2,3 7 9 4,5 6 h H2,1,2,3 H2,4,5,6 q 2 2 p 4 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey OMSYGYSPFZQFFP UHFFFAOYSA J CASNo 7446 26 6 Section2 Chembox Properties Formula Zn sub 2 sub P sub 2 sub O sub 7 sub MolarMass 304.72 g mol Appearance white crystalline powder Density 3.75 g cm sup 3 sup MeltingPt BoilingPt Solubility insoluble SolubleOther soluble in dilute acid s Section3 Chembox Structure CrystalStruct Section7 Chembox Hazards EUClass Zinc pyrophospate Zn sub 2 sub P sub 2 sub O sub 7 sub is an inorganic chemical compound . It is useful in gravimetric analysis of zinc. Zinc pyrophosphate is obtained by precipitating zinc as a phosphate, then heating over 1123 K. Fact date May 2009 References Reflist Zinc compounds Category Pyrophosphates Category Zinc compounds inorganic compound stub el ... more details
Chembox verifiedrevid 457790064 ImageFile Tetraethyl pyrophosphate.png ImageSize IUPACName tetraethyl diphosphate OtherNames Section1 Chembox Identifiers CASNo Ref cascite correct CAS CASNo 107 49 3 ChEMBL Ref ebicite correct EBI ChEMBL 293787 PubChem 7873 ChemSpiderID Ref chemspidercite correct chemspider ChemSpiderID 7585 SMILES O P OP O OCC OCC OCC OCC InChI 1 C8H20O7P2 c1 5 11 16 9,12 6 2 15 17 10,13 7 3 14 8 4 h5 8H2,1 4H3 InChIKey IDCBOTIENDVCBQ UHFFFAOYAI StdInChI Ref stdinchicite correct chemspider StdInChI 1S C8H20O7P2 c1 5 11 16 9,12 6 2 15 17 10,13 7 3 14 8 4 h5 8H2,1 4H3 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey IDCBOTIENDVCBQ UHFFFAOYSA N Section2 Chembox Properties C 8 H 20 O 7 P 2 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition Tetraethyl pyrophosphate , abbreviated TEPP, is an organophosphate compound . It is used as a pesticide . This compound is a clear, colorless liquid. It is soluble in water, but hydrolyzes rapidly. ref Ullmann s doi 10.1002 14356007.a14 263 title Insect Control author Robert L. Metcalf ref It was first synthesized by Philippe de Clermont . This compound may be prepared by two equivalents of diethyl chlorophosphate with one equivalent of water in the presence of pyridine to scavenge the hydrogen chloride formed ref cite journal doi 10.1021 ja01191a104 journal J. Am. Chem. Soc. year 1948 last1 Toy first1 A. D. F. volume 70 issue 11 pages 3882 title The Preparation of Tetraethyl Pyrophosphate and Other Tetraalkyl Pyrophosphates ref File Synthesis of tetraethyl pyrophosphate.png 400px References References Category Pyrophosphates sr Tetraetil pirofosfat fi Tetraetyylipyrofosfaatti ... more details
, which is in turn connected to a pyrophosphate diphosphate functional group . The part of TPP molecule ... The TPP thiazolium ring can be deprotonated at C2 to become an ylid. Image Thiamine pyrophosphate ... Thiazoles Category Pyrimidines Category B vitamins de Thiaminpyrophosphat fr Thiamine pyrophosphate ... more details
enzyme Name farnesyl diphosphate kinase EC number 2.7.4.18 CAS number 50936 43 1 IUBMB EC number 2 7 4 18 GO code 0047887 image width caption In enzymology , a farnesyl diphosphate kinase EC number 2.7.4.18 is an enzyme that catalysis catalyzes the chemical reaction ATP farnesyl diphosphate math rightleftharpoons math ADP farnesyl triphosphate Thus, the two substrate biochemistry substrates of this enzyme are adenosine triphosphate ATP and farnesyl diphosphate , whereas its two product chemistry products are adenosine diphosphate ADP and farnesyl triphosphate . This enzyme belongs to the family of transferase s, specifically those transferring phosphorus containing groups phosphotransferase s with a phosphate group as acceptor. The systematic name of this enzyme class is ATP farnesyl diphosphate phosphotransferase . This enzyme is also called farnesylpyrophosphate kinase . References reflist 1 cite journal author Shechter I date 1974 title Phosphate transfer from trans farnesyl triphosphate to AMP in Gibberella fujikuroi journal Biochim. Biophys. Acta. volume 362 pages 233&ndash 44 pmid 4423368 issue 2 enzyme stub Category EC 2.7.4 Category Enzymes of unknown structure ... more details
protein Name farnesyl diphosphate farnesyltransferase 1 caption image width HGNCid 3629 Symbol FDFT1 AltSymbols EntrezGene 2222 OMIM 184420 RefSeq NM 004462 UniProt P37268 PDB ECnumber 2.5.1.21 Chromosome 8 Arm p Band 23.1 LocusSupplementaryData p22 Farnesyl diphosphate farnesyltransferase FDFT1 or squalene synthase SQS is an enzyme that converts two units of farnesylpyrophosphate into squalene . Image Cholesterol Synthesis Reaction10.png thumb center 600px Reaction It has been described as the first dedicated enzyme of sterol i.e., cholesterol , etc. synthesis, since the squalene formed by it is exclusively routed into various sterols via a complex, multi step pathway. Diversity Squalene synthase is considered to be an enzyme of eukaryote s or advanced organisms, although at least one prokaryote has been shown to possess a functionally similar enzyme. In terms of structure and mechanics, squalene synthase most closely resembles phytoene synthase , which serves a similar role in many plants in the elaboration of phytoene , a precursor of many carotenoid compounds. Carotenoids are the colorful pigments present in most vegetables. Interactive pathway map StatinPathway WP430 highlight Squalene Clinical significance Inhibition of squalene synthase, e.g., by lapaquistat , is under investigation as a method of lowering cholesterol levels in the prevention of cardiovascular disease. ref cite journal last Davidson first MH year 2007 month January title Squalene synthase inhibition a novel target for the management of dyslipidemia journal Curr Atheroscler Rep volume 9 issue 1 pages 78 80 pmid 17169251 doi 10.1007 BF02693932 ref ref name pmid17209661 cite journal author Charlton Menys V, Durrington PN title Squalene synthase inhibitors clinical pharmacology and cholesterol lowering potential journal Drugs volume 67 issue 1 pages 11 6 year 2007 pmid 17209661 doi url ref It has also ... External links MeshName Farnesyl Diphosphate Farnesyltransferase Alkyl and aryl transferases Ketone ... more details
enzyme Name Z farnesyl diphosphate synthase EC number 2.5.1.68 CAS number IUBMB EC number 2 5 1 68 GO code image width caption In enzymology , a Z farnesyl diphosphate synthase EC number 2.5.1.68 is an enzyme that catalysis catalyzes the chemical reaction geranyl diphosphate isopentenyl diphosphate math rightleftharpoons math diphosphate 2Z,6E farnesyl diphosphate Thus, the two substrate biochemistry substrates of this enzyme are geranyl diphosphate and isopentenyl diphosphate , whereas its two product chemistry products are diphosphate and 2Z,6E farnesyl diphosphate . This enzyme belongs to the family of transferase s, specifically those transferring aryl or alkyl groups other than methyl groups. The systematic name of this enzyme class is geranyl diphosphate isopentenyl diphosphate geranylcistransferase . This enzyme is also called Z farnesyl diphosphate synthase . References reflist 1 cite journal author F, Bertini S, Brennan PJ, Crick DC date 2001 title Purification, enzymatic characterization, and inhibition of the Z farnesyl diphosphate synthase from Mycobacterium tuberculosis journal J. Biol. Chem. volume 276 pages 11624&ndash 30 pmid 11152452 doi 10.1074 jbc.M007168200 issue 15 transferase stub Category EC 2.5.1 Category Enzymes of unknown structure ... more details
DISPLAYTITLE E 4 Hydroxy 3 methyl but 2 enyl pyrophosphate chembox verifiedrevid 456493945 Name E 4 Hydroxy 3 methyl but 2 enyl pyrophosphate ImageFile HMB PP.PNG ImageSize 190px ImageName Chemical structure of HMB PP ImageFile1 HMBPP 3D balls.png ImageSize1 240px ImageName1 Ball and stick model, shown here as a 3 ion IUPACName E 4 hydroxy 3 methylbut 2 enoxy oxidophosphoryl phosphate OtherNames E 4 hydroxy dimethylallyl pyrophosphate br HDMAPP br E 4 Hydroxy 3 methyl but 2 enyl diphosphate br HMBDP Section1 Chembox Identifiers ChemSpiderID Ref chemspidercite correct chemspider ChEBI Ref ebicite correct EBI ChEBI 15664 ChemSpiderID 4445244 InChI 1 C5H12O8P2 c1 5 4 6 2 3 12 15 10,11 13 14 7,8 9 h2,6H,3 4H2,1H3, H,10,11 H2,7,8,9 b5 2 InChIKey MDSIZRKJVDMQOQ GORDUTHDBB SMILES1 O P OP O O O OC C C CO C O StdInChI Ref stdinchicite correct chemspider StdInChI 1S C5H12O8P2 c1 5 4 6 2 3 12 15 10,11 13 14 7,8 9 h2,6H,3 4H2,1H3, H,10,11 H2,7,8,9 b5 2 StdInChIKey Ref stdinchicite correct chemspider StdInChIKey MDSIZRKJVDMQOQ GORDUTHDSA N CASNo Ref cascite correct ?? CASNo ChEMBL Ref ebicite correct EBI ChEMBL 145233 PubChem 21597501 SMILES CC CCOP O O OP O O O CO Section2 Chembox Properties C 5 H 12 O 8 P 2 Appearance Density MeltingPt BoilingPt Solubility Section3 Chembox Hazards MainHazards FlashPt Autoignition E 4 Hydroxy 3 methyl but 2 enyl pyrophosphate HMBPP or HMB PP is an intermediate of the non mevalonate pathway of isoprenoid biosynthesis. ref name Rohmer cite journal last1 Rohmer first1 M title The discovery of a mevalonate independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants journal Natural product reports volume 16 issue 5 pages 565 74 year 1999 pmid 10584331 doi 10.1039 a709175c last2 Rohmer first2 Michel ref ref name Poulter cite journal ... pyrophosphate IPP and dimethylallyl pyrophosphate DMAPP by HMB PP reductase LytB, IspH . HMB ... links MeshName 4 hydroxy 3 methylbut 2 enyl pyrophosphate DEFAULTSORT Hydroxymethylbutenyl pyrophosphate ... more details
protein Name farnesyl diphosphate synthase farnesylpyrophosphate synthetase, dimethylallyltranstransferase, geranyltranstransferase caption image width HGNCid 3631 Symbol FDPS AltSymbols EntrezGene 2224 OMIM 134629 RefSeq NM 002004 UniProt P14324 PDB ECnumber 2.5.1.1 Chromosome 1 Arm q Band 22 LocusSupplementaryData Dimethylallyltranstransferase is an enzyme that converts dimethylallylpyrophosphate and isopentenyl pyrophosphate into farnesylpyrophosphate . It is also referred to as farnesylpyrophosphate synthase or farnesyldiphosphate synthase. Pyrophosphate is also involved, as both a reactant and a product. Geranylpyrophosphate is created in an intermediate step. See also Geranyltranstransferase External links MeshName Dimethylallyltranstransferase transferase stub Alkyl and aryl transferases Ketone and cholesterol metabolism enzymes fi Dimetyyliallyylitranstransferaasi ... more details
Sesquiterpenes are a class of terpene s that consist of three isoprene units and have the molecular formula C sub 15 sub H sub 24 sub . Like monoterpenes , sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as redox oxidation or rearrangement reaction rearrangement produce the related sesquiterpenoids . Sesquiterpenes are found naturally in plants and insects, as semiochemical s, e.g. defensive agents or pheromones. Acyclic When geranyl pyrophosphate reacts with isopentenyl pyrophosphate , the result is the 15 carbon farnesyl pyrophosphate , which is an intermediate in the biosynthesis of sesquiterpenes such as farnesene . Oxidation can then provide sesquiterpenoids such as farnesol . Image Farnesyl pyrophosphate.png thumb 300px none Farnesyl pyrophosphate Monocyclic With the increased chain length and additional double bond, the number of possible ways that cyclization can occur is also increased, and there exists a wide variety of cyclic sesquiterpenes. In addition to common six membered ring systems such as is found in zingiberene , a constituent of the oil from ginger , cyclization of one end of the chain to the other end can lead to macrocyclic rings such as humulene . Bicyclic image Cadinene.png thumb right 100px &delta Cadinene, a sesquiterpene In addition to common six membered rings such as in the cadinene s, one classic bicyclic sesquiterpene is caryophyllene , from the oil of clove s, which has a nine membered ring and cyclobutane ring. Additional unsaturation provides aromatic bicyclic sesquiterpenoids such as vetivazulene and guaiazulene . Tricyclic With the addition of a third ring, the possible structures become increasingly varied. Examples include longifolene , copaene and the alcohol patchoulol . External links MeshName Sesquiterpenes Category Sesquiterpenes es Sesquiterpeno fr Sesquiterp ne pl Seskwiterpeny pt Sesquiterpeno ru fi Seskviterpeeni ... more details
enzyme Name aristolochene synthase EC number 4.2.3.9 CAS number IUBMB EC number 4 2 3 9 GO code 0045483 image width caption In enzymology , an aristolochene synthase EC number 4.2.3.9 is an enzyme that catalysis catalyzes the chemical reaction 2 trans,6 trans farnesyl diphosphate math rightleftharpoons math aristolochene diphosphate Hence, this enzyme has one substrate biochemistry substrate , 2 trans,6 trans farnesyl diphosphate , and two product chemistry products , aristolochene and diphosphate . This enzyme belongs to the family of lyase s, specifically those carbon oxygen lyases acting on phosphates. The systematic name of this enzyme class is 2 trans,6 trans farnesyl diphosphate diphosphate lyase cyclizing, aristolochene forming . Other names in common use include sesquiterpene cyclase , trans,trans farnesyl diphosphate aristolochene lyase , trans,trans farnesyl diphosphate diphosphate lyase cyclizing, , and aristolochene forming . This enzyme participates in terpenoid biosynthesis . Structural studies As of late 2007, two tertiary structure structures have been solved for this class of enzymes, with Protein Data Bank PDB accession codes PDB link 2E4O and PDB link 2OA6 . They are both notable for the very high helix content of the structure. References reflist 1 cite journal author Cane DE, Prabhakaran PC, Oliver JS and McIlwaine DB date 1990 title Aristolochene biosynthesis. Stereochemistry of the deprotonation steps in the enzymatic cyclization of farnesyl pyrophosphate journal J. Am. Chem. Soc. volume 112 issue 8 pages 3209&ndash 3210 doi 10.1021 ja00164a051 cite journal author Noguchi H and Rawlings BJ date 1989 title Aristolochene biosynthesis and enzymatic cyclization of farnesyl pyrophosphate journal J. Am. Chem. Soc. volume 111 issue 24 pages 8914&ndash 8916 doi 10.1021 ja00206a022 cite journal author Hohn TM, Plattner RD date 1989 title Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti jo ... more details
enzyme Name farnesyltranstransferase EC number 2.5.1.29 CAS number 9032 58 0 IUBMB EC number 2 5 1 29 GO code 0004311 image width caption In enzymology , a farnesyltranstransferase EC number 2.5.1.29 is an enzyme that catalysis catalyzes the chemical reaction trans,trans farnesyl diphosphate isopentenyl diphosphate math rightleftharpoons math diphosphate geranylgeranyl diphosphate Thus, the two substrate biochemistry substrates of this enzyme are trans,trans farnesyl diphosphate and isopentenyl diphosphate , whereas its two product chemistry products are diphosphate and geranylgeranyl diphosphate . This enzyme belongs to the family of transferase s, specifically those transferring aryl or alkyl groups other than methyl groups. The systematic name of this enzyme class is trans,trans farnesyl diphosphate isopentenyl diphosphate farnesyltranstransferase . Other names in common use include geranylgeranyl diphosphate synthase , geranylgeranyl pyrophosphate synthetase , geranylgeranyl PP synthetase , farnesyltransferase , and geranylgeranyl pyrophosphate synthase . This enzyme participates in biosynthesis of steroids and terpenoid biosynthesis . Structural studies As of late 2007, two tertiary structure structures have been solved for this class of enzymes, with Protein Data Bank PDB accession codes PDB link 2DH4 and PDB link 2Q80 . References reflist 1 cite journal author Sagami H, Ishi K and Ogura K date 1981 title Occurrence and unusual properties of geranylgeranyl pyrophosphate synthetase of pig liver journal Biochem. Int. volume 3 pages 669&ndash 675 transferase stub Category EC 2.5.1 Category Enzymes of known structure ... more details
Tokyo title The purification of prenyltransferase and isopentenyl pyrophosphate isomerase of pumpkin ... doi 10.1021 bi00672a009 issue 1 cite journal author Takahashi I, Ogura K date Tokyo title Farnesylpyrophosphate synthetase from Bacillus subtilis journal J. volume Biochem. pages 1581&ndash 7 ... subtilis undecaprenyl pyrophosphate synthetase and geranylgeranyl pyrophosphate synthetase ... more details
enzyme Name pentalenene synthase EC number 4.2.3.7 CAS number 90597 46 9 IUBMB EC number 4 2 3 7 GO code 0050467 image width caption In enzymology , a pentalenene synthase EC number 4.2.3.7 is an enzyme that catalysis catalyzes the chemical reaction 2 trans,6 trans farnesyl diphosphate math rightleftharpoons math pentalenene diphosphate Hence, this enzyme has one substrate biochemistry substrate , 2 trans,6 trans farnesyl diphosphate , and two product chemistry products , pentalenene and diphosphate . This enzyme belongs to the family of lyase s, specifically those carbon oxygen lyases acting on phosphates. The systematic name of this enzyme class is 2 trans,6 trans farnesyl diphosphate diphosphate lyase cyclizing, pentalenene forming . This enzyme is also called pentalenene synthetase . References reflist 1 cite journal author Cane DE date 1983 title Cell free studies of monoterpene and sesquiterpene biosynthesis journal Biochem. Soc. Trans. volume 11 pages 510&ndash 5 pmid 6642060 issue 5 cite journal author Cane DE and Tillman AM date 1983 title Pentalenene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate journal J. Am. Chem. Soc. volume 105 pages 122&ndash 124 doi 10.1021 ja00339a026 cite journal author JS, Hubbard BR date 1994 title Pentalenene synthase. Purification, molecular cloning, sequencing, and high level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319 journal Biochemistry. volume 33 pages 5846&ndash 57 pmid 8180213 doi 10.1021 bi00185a024 last2 Sohng first2 JK last3 Lamberson first3 CR last4 Rudnicki first4 SM last5 Wu first5 Z last6 Lloyd first6 MD last7 Oliver first7 JS last8 Hubbard first8 BR issue 19 4.2 enzyme stub Category EC 4.2.3 Category Enzymes of unknown structure ... more details
CVS is a cyclase terpene cyclase enzyme responsible for the biosynthesis of valencene , a sesquiterpene , using farnesyl pyrophosphate as its substrate. The first CVS enzyme was isolated using orange fruit orange cDNA . ref cite journal last Sharon Asa first Liat authorlink coauthors Moshe Shalit, Ahuva Frydman, Einat Bar, Doron Holland, Etti Or, Uri Lavi, Efraim Lewinsohn, Yoram Eyal title Citrus fruit flavor and aroma biosynthesis isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene. journal The Plant Journal volume 2003 issue 36 pages 664 674 publisher Blackwell Publishing Ltd. location year 2003 url doi id accessdate pmid 14617067 ref References reflist Category Enzymes enzyme stub ... more details
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