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Information on EC 2.5.1.31 - ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]
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2.5.1.31 ditrans,polycis-undecaprenyl-diphosphate synthase [(2E,6E)-farnesyl-diphosphate specific]IUBMB Comments
Undecaprenyl pyrophosphate synthase catalyses the consecutive condensation reactions of a farnesyl diphosphate with eight isopentenyl diphosphates, in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall .
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Word Map
- 2.5.1.31
-
isoprenoids
- cis-prenyltransferase
- prenyltransferases
- dolichols
- luteus
- dhdds
- trans-prenyltransferases
- pharmacology
-
octaprenyl
- drug development
- medicine
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
undecaprenyl diphosphate synthase, undecaprenyl pyrophosphate synthase, dehydrodolichyl diphosphate synthase, upp synthase, ddpps, undecaprenyl pyrophosphate synthetase, upp synthetase, z-prenyl diphosphate synthase, isosesquilavandulyl diphosphate synthase, undecaprenyl-diphosphate synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
bactoprenyl-diphosphate synthase
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C55-OO synthetase
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C55PP synthetase
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cis,polyprenyl diphosphate synthase
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cis-prenyl chain elongating enzyme
CPDS
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DDPPs
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dehydrodolichyl diphosphate synthase
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di-trans,poly-cis-decaprenylcistransferase
di-trans,poly-cis-undecaprenyl-diphosphate synthase
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di-trans-poly-cis-decaprenyl cistransferase
synthetase, undecaprenyl pyrophosphate
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undecaprenyl diphosphate synthase
undecaprenyl diphosphate synthetase
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undecaprenyl pyrophosphate synthase
undecaprenyl pyrophosphate synthetase
undecaprenyl-diphosphate synthase
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UPP synthase
UPP synthetase
UPP, C55 synthase
UPPs
UPS
Z-prenyl diphosphate synthase
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additional information
undecaprenyl diphosphate synthase
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undecaprenyl diphosphate synthase
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undecaprenyl pyrophosphate synthase
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undecaprenyl pyrophosphate synthetase
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UPP synthetase
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UPPs
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UPPs
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UPS
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
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-
-
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
active site structure and catalytic mechanism
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
active site structure, detailed catalytic mechanism, substrate binding mechanism, D26, H43, S71, N74, and R77 are involved
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
substrate binding mode and catalytic mechanism involving active site residue Asp26 which serves as general base, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
ditrans,octacis-undecaprenyl diphosphate substrate binding mode and catalytic mechanism involving active site residue Asp26 which serves as general base, overview
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalytic mechanism, overview
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
alkenyl group transfer
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PATHWAY SOURCE
PATHWAYS
BRENDA
KEGG
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate:isopentenyl-diphosphate cistransferase (adding 8 isopentenyl units)
Undecaprenyl pyrophosphate synthase catalyses the consecutive condensation reactions of a farnesyl diphosphate with eight isopentenyl diphosphates, in which new cis-double bonds are formed, to generate undecaprenyl diphosphate that serves as a lipid carrier for peptidoglycan synthesis of bacterial cell wall [3].
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CAS REGISTRY NUMBER
COMMENTARY
52350-87-5
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-8-(N-methyl-2-aminobenzoyloxy)-3,7-dimethyl-2,6-octandien-1-diphosphate + 8 isopentenyl diphosphate
?
-
a fluorescent analog of farnesyl diphosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans,poly-cis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + isopentenyl diphosphate
diphosphate + ditrans,polycis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl thiodiphosphate + isopentenyl diphosphate
?
-
weak activity, 10000000fold lower than with (2E,6E)-farnesyl diphosphate
-
-
?
(2Z,6E,10E,14E)-farnesylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6Z,10E,14E)-farnesylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(E)-3-methyl-3-pentenyl diphosphate + isopentenyl diphosphate
?
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reactive as substrate and competitive inhibition profile
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-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
7-(2,6-dimethyl-8-diphospho-2,6-octadienyloxy)-8-methyl-4-trifluoromethyl-chromen-2-one geranyl diphosphate + isopentenyl diphosphate
?
-
fluorescent analogue of (2E,6E)-farnesyl diphosphate, alternative substrate and inhibitor
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-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + undecaprenyl diphosphate
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neither dimethylallyl diphosphate nor geranyl diphosphate act as priming substrate for the enzyme
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-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
farnesyl phosphate + isopentenyl diphosphate
phosphate + di-trans-poly-cis-undecaprenyl diphosphate
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low activity
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?
geranyl diphosphate + isopentenyl diphosphate
?
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C10 GPP displays a 90fold larger Km value compared with (2E,6E)-farnesyl diphosphate
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?
geranyl diphosphate + isopentenyl diphosphate
diphosphate + ?
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less effective than farnesyl diphosphate
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?
geranylgeranyl diphosphate + isopentenyl diphosphate
?
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containing a larger C20 hydrocarbon tail, is an equally good substrate
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?
geranylgeranyl diphosphate + isopentenyl diphosphate
diphosphate + ?
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as effective as farnesyl diphosphate
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?
isopentenyl diphosphate + (E,E)-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
(E,E)-(2-diazo-3-trifluoropropionyloxy)polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + dimethylallyl diphosphate
?
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2% of the activity with farnesyl diphosphate
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?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + geranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + geranylgeranyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + geranylneryl diphosphate
?
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cis,trans,trans-geranylneryl diphosphate
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-
?
isopentenyl diphosphate + neryl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
isopentenyl diphosphate + S-farnesyl thiodiphosphate
?
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weak activity, 10000000fold lower than with farnesyl diphosphate
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-
?
N-(4-benzoylphenyl)-4-hydroxy-2-oxo-5-phenethyl-2,5-dihydro-1H-pyrrole-3-carboxamide + isopentenyl diphosphate
?
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Photo-probe
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-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
quantification of product distribution of UPPs catalyzed coupling of (2E,6E)-farnesyl diphosphate and isopentenyl diphosphate under various reaction conditions
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
catalyzes the condensation of eight molecules of isopentenyl pyrophosphate (IPP) with farnesyl diphosphate (FPP) to generate C55 undecaprenyl diphosphate. With a variety of different ratios of enzyme to substrate and FPP to IPP in the presence or absence of Triton, different product distributions are found
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
UPPS catalyzes eight consecutive condensation steps of IPP with FPP to form C55 final product
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme is responsible for the biogenesis of undecaprenyl phosphate, an indispensable glycosyl carrier lipid in bacterial cell wall biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme is responsible for the biogenesis of undecaprenyl phosphate, an indispensable glycosyl carrier lipid in bacterial cell wall biosynthesis
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
trans,trans-farnesyl diphosphate
C55 polyprenyl diphosphate with isoprene residues with cis stereochemistry
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the cis-prenyl chain elongation onto trans,trans-farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP). The product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the sequential condensation of eight molecules of isopentenyl diphosphate (IPP) in the cis-configuration into farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP), which is indispensable for the biosynthesis of the bacterial cell wall
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the cis-prenyl chain elongation onto trans,trans-farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP). The product undecaprenyl diphosphate is indispensable for the biosynthesis of bacterial cell walls
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
catalyzes the sequential condensation of eight molecules of isopentenyl diphosphate (IPP) in the cis-configuration into farnesyl diphosphate (FPP) to produce undecaprenyl diphosphate (UPP), which is indispensable for the biosynthesis of the bacterial cell wall
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
the enzyme catalyzes the synthesis of the C55 lipid undecaprenyl diphosphate through eight consecutive condensations of isopentenyl pyrophosphate
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
-
-
-
?
(2E,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2E,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2E,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
(2Z,6E,10E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
?
(Z,E)-geranylgeranyl diphosphate + isopentenyl diphosphate
?
-
-
-
-
?
2-amideanilinogeranyl diphosphate + isopentenyl diphosphate
?
lower activity, the fluorescent substrate analogue undergoes a 1.2fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
ESI-MS analysis suggests that these major product peaks correspond to six to nine Z-configuration isoprenes incorporated by the UPPS protein
-
?
2-amideanilinogeranyl diphosphate + isopentenyl diphosphate
?
lower activity, the fluorescent substrate analogue undergoes a 1.2fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
ESI-MS analysis suggests that these major product peaks correspond to six to nine Z-configuration isoprenes incorporated by the UPPS protein
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
2-nitrileanilinogeranyl diphosphate + 9 isopentenyl diphosphate
9 diphosphate + 2-nitrileanilinobactoprenyl diphosphate
the fluorescent substrate analogue undergoes a 2.5fold increase in fluorescence upon isoprenoid chain elongation, and this increase in fluorescence can be utilized to monitor the activity and inhibition of UPPS in 96-well plate assays
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate, the diphosphate head group of farnesyl diphosphate is bound to the backbone of NHs pf G29 and R30 as well as the side chains of N28, R30, and R39 through hydrogen bonds, H43 may stabilize the farnesyl cation intermediate during catalysis being near to the C2 carbon of farnesyl diphosphate
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate, isopentenyl diphosphate binding mode determination
-
-
?
di-trans-poly-cis-decaprenyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
di-trans-poly-cis-decaprenyl diphosphate is farnesyl diphosphate, isopentenyl diphosphate binding mode determination
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55 chain length
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
consecutive condensation of 8 molecules of isopentenyl diphosphate with farnesyl diphosphate to form the lipid carrier undecaprenyl diphosphate to mediate bacterial peptidoglycan synthesis, the final product has C55-C60 chain length, molecular 3D-structural modeling of the reaction product
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
stereochemistry of the reaction
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
the phosphate head group of farnesyl diphosphate is bound to the positively charged Arg residues and the hydrocarbon moiety interacts with hydrophobic amino acids including L85, L88, and F89, located on the alpha3-helix of the enzyme
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
-
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
sequential condensation of 8 molecules of isopentenyl diphosphate in the cis-configuration into farnesyl diphosphate to produce undecaprenyl diphosphate, indispensable for the biosynthesis of bacterial cell wall
-
-
?
farnesyl diphosphate + isopentenyl diphosphate
diphosphate + di-trans-poly-cis-undecaprenyl diphosphate
sequential condensation of 8 molecules of isopentenyl diphosphate in the cis-configuration into farnesyl diphosphate to produce undecaprenyl diphosphate, indispensable for the biosynthesis of bacterial cell wall
-
-
?
isopentenyl diphosphate + (E,E)-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
(E,E)-(2-diazo-3-trifluoropropionyloxy)polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + (E,E)-(2-diazo-3-trifluoropropionyloxy)geranyl diphosphate
(E,E)-(2-diazo-3-trifluoropropionyloxy)polyprenyl diphosphate + diphosphate
-
47% of the activity with trans,trans-farnesyl diphosphate
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
-
-
-
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
(E,E)-farnesyl diphosphate or (Z,E)-farnesyl diphosphate
C50-polyprenyl diphosphate and C55-polyprenyl diphosphate in the ratio of 3:1 from (Z,E,E,E)-farnesylgeranyl diphosphate and in the ratio 3:2 from (Z,Z,E,E)-farnesylgeranyl diphosphate, C50-polyprenyl diphosphate and C55-polyprenyl diphosphate with Z,E mixed stereochemistry, formation of C50-polyprenyl diphosphate and C55-polyprenyl diphosphate in the ratio of 1:4 from (E,E)-farnesyl diphosphate and in the ratio of 4:1 from (Z,E)-farnesyl diphosphate
?
isopentenyl diphosphate + farnesyl diphosphate
C55-polyprenyl diphosphate + C50-polyprenyl diphosphate + diphosphate
-
(Z,E,E,E)-farnesylgeranyl diphosphate or (Z,Z,E,E)-farnesylgeranyl diphosphate
C50-polyprenyl diphosphate and C55-polyprenyl diphosph