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IUBMB CommentsThis enzyme is involved in the biosynthesis of the glycosyl carrier lipid in some archaebacteria. Unlike EC 2.5.1.31, its counterpart in most bacteria, it prefers geranylgeranyl diphosphate to farnesyl diphosphate as the allylic substrate, resulting in production of a tritrans,polycis variant of undecaprenyl diphosphate .
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(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate
8 diphosphate + ditrans,octacis-undecaprenyl diphosphate
about 35% of the activity with geranylgeranyl diphosphate
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all-trans-geranylfarnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + hexatrans,tetracis-undecaprenyl diphosphate
geranylgeranyl diphosphate + 7 isopentenyl diphosphate
7 diphosphate + tritrans,heptacis-undecaprenyl diphosphate
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additional information
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all-trans-geranylfarnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + hexatrans,tetracis-undecaprenyl diphosphate
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i.e. (Z,Z,Z,Z,Z,Z,E,E,E,E)-UPP [(2Z,6Z,10Z,14Z,18Z,22Z,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yl diphosphate]
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all-trans-geranylfarnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + hexatrans,tetracis-undecaprenyl diphosphate
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additional information
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the undecaprenyl diphosphate synthase from Aeropyrum pernix that has anomalous substrate specificity, due to the fact that only dimethylallyl diphosphate and geranylfarnesyl diphosphate, both of which are unusual substrates for known cis-prenyltransferases, are likely available as an allylic primer substrate for the archaeal enzyme
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additional information
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the enzyme is a cis-prenyltransferas, determination of substrate specificity, product chain-length, and cofactor requirement, overview. The most preferred allylic substrates are farnesyl diphosphate and geranylfarnesyl diphosphate, the main product is UPP, regardless of the substrate. When the ratio of IPP to geranylfarnesyl diphosphate is decreased to 1, the UPP synthase predominately yields shorter C30-45 products. When the ratio is increased to 100, the main product is C60 dodecaprenyl diphosphate. The chain-length of the product of UPP synthase, which determines the structure of the glycosyl carrier lipid, is variable depending on the substrate ratio in the cells of Aeropyrum pernix. A 10fold increase in the substrate ratio results in a significant rise in the production of all-trans-hexaprenyl diphosphate. No activity with dimethylallyl diphosphate. The enzyme also shows the activity of hexaprenyl diphosphate synthase [geranylgeranyl-diphosphate specific], EC 2.5.1.82, and of geranylgeranyl diphosphate synthase, EC 2.5.1.29
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additional information
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the undecaprenyl diphosphate synthase from Aeropyrum pernix that has anomalous substrate specificity, due to the fact that only dimethylallyl diphosphate and geranylfarnesyl diphosphate, both of which are unusual substrates for known cis-prenyltransferases, are likely available as an allylic primer substrate for the archaeal enzyme
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additional information
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the enzyme is a cis-prenyltransferas, determination of substrate specificity, product chain-length, and cofactor requirement, overview. The most preferred allylic substrates are farnesyl diphosphate and geranylfarnesyl diphosphate, the main product is UPP, regardless of the substrate. When the ratio of IPP to geranylfarnesyl diphosphate is decreased to 1, the UPP synthase predominately yields shorter C30-45 products. When the ratio is increased to 100, the main product is C60 dodecaprenyl diphosphate. The chain-length of the product of UPP synthase, which determines the structure of the glycosyl carrier lipid, is variable depending on the substrate ratio in the cells of Aeropyrum pernix. A 10fold increase in the substrate ratio results in a significant rise in the production of all-trans-hexaprenyl diphosphate. No activity with dimethylallyl diphosphate. The enzyme also shows the activity of hexaprenyl diphosphate synthase [geranylgeranyl-diphosphate specific], EC 2.5.1.82, and of geranylgeranyl diphosphate synthase, EC 2.5.1.29
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additional information
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dimethylallyl diphosphate and geranyl diphosphate scarcely react
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all-trans-geranylfarnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + hexatrans,tetracis-undecaprenyl diphosphate
additional information
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all-trans-geranylfarnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + hexatrans,tetracis-undecaprenyl diphosphate
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all-trans-geranylfarnesyl diphosphate + 6 isopentenyl diphosphate
6 diphosphate + hexatrans,tetracis-undecaprenyl diphosphate
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additional information
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the undecaprenyl diphosphate synthase from Aeropyrum pernix that has anomalous substrate specificity, due to the fact that only dimethylallyl diphosphate and geranylfarnesyl diphosphate, both of which are unusual substrates for known cis-prenyltransferases, are likely available as an allylic primer substrate for the archaeal enzyme
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additional information
?
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the undecaprenyl diphosphate synthase from Aeropyrum pernix that has anomalous substrate specificity, due to the fact that only dimethylallyl diphosphate and geranylfarnesyl diphosphate, both of which are unusual substrates for known cis-prenyltransferases, are likely available as an allylic primer substrate for the archaeal enzyme
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?
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Hemmi, H.; Yamashita, S.; Shimoyama, T.; Nakayama, T.; Nishino, T.
Cloning, expression, and characterization of cis-polyprenyl diphosphate synthase from the thermoacidophilic archaeon Sulfolobus acidocaldarius
J. Bacteriol.
183
401-404
2001
Sulfolobus acidocaldarius (Q9HH76)
brenda
Mori, T.; Ogawa, T.; Yoshimura, T.; Hemmi, H.
Substrate specificity of undecaprenyl diphosphate synthase from the hyperthermophilic archaeon Aeropyrum pernix
Biochem. Biophys. Res. Commun.
436
230-234
2013
Aeropyrum pernix (Q9YC66), Aeropyrum pernix DSM 11879 (Q9YC66)
brenda
Grabinska, K.A.; Park, E.J.; Sessa, W.C.
cis-Prenyltransferase new insights into protein glycosylation, rubber synthesis, and human diseases
J. Biol. Chem.
291
18582-18590
2016
Sulfolobus acidocaldarius (Q9HH76)
brenda
2.5.1.89 tritrans,polycis-undecaprenyl diphosphate synthase [geranylgeranyl-diphosphate specific]
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