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Information on EC 2.4.1.331 - 8-demethyltetracenomycin C L-rhamnosyltransferase
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EC Tree 2 Transferases
2.4 Glycosyltransferases
2.4.1 Hexosyltransferases
2.4.1.331 8-demethyltetracenomycin C L-rhamnosyltransferase
IUBMB Comments
Isolated from Streptomyces olivaceus Tü2353. Involved in elloramycin biosynthesis. In vitro it can also utilize other 6-deoxy D- or L-hexoses.
The enzyme appears in viruses and cellular organisms
- 2.4.1.331
-
tetracenomycins
-
aglycone
-
deoxysugars
- lividans
- olivaceus
- synthesis
- oleandomycin
- polyketide
- glycosyltransferases
- 4-ketoreductase
- medicine
Reaction Schemes
showSynonyms
elmgt, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
elloramycin glycosyltransferase
ElmGT
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C = dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
elloramycin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
dTDP-beta-L-rhamnose:8-demethyltetracenomycin C 3-alpha-L-rhamnosyltransferase
Isolated from Streptomyces olivaceus Tu2353. Involved in elloramycin biosynthesis. In vitro it can also utilize other 6-deoxy D- or L-hexoses.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
NDP-4-dehydro-L-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-(4-dehydro-L-olivosyl)tetracenomycin C
NDP-D-amicetose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-amicetyltetracenomycin C
NDP-D-glucose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-glucosyltetracenomycin C
NDP-D-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-olivosyltetracenomycin C
NDP-L-amicetose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-amicetyltetracenomycin C
NDP-L-boivinose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-boivinosyltetracenomycin C
NDP-L-digitose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-digitoxosyltetracenomycin C
NDP-L-digitoxose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-digitoxosyltetracenomycin C
NDP-L-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-olivosylyltetracenomycin C
NDP-L-rhamnose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: the enzyme is involved in biosynthesis of the antitumor polyketide elloramycin
Products: -
Products: -
?
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: dTDP-beta-L-rhamnose i.e. dTDP-6-deoxy-beta-L-mannose
Products: -
Products: -
?
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: the enzyme is involved in biosynthesis of the antitumor polyketide elloramycin
Products: -
Products: -
?
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: dTDP-beta-L-rhamnose i.e. dTDP-6-deoxy-beta-L-mannose
Products: -
Products: -
?
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-4-dehydro-L-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-(4-dehydro-L-olivosyl)tetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-4-dehydro-L-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-(4-dehydro-L-olivosyl)tetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-D-amicetose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-amicetyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-D-amicetose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-amicetyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-D-glucose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-glucosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-D-glucose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-glucosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-D-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-olivosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-D-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-olivosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-amicetose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-amicetyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-amicetose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-amicetyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-boivinose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-boivinosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-boivinose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-D-boivinosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-digitose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-digitoxosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-digitose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-digitoxosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-digitoxose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-digitoxosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-digitoxose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-digitoxosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-olivosylyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-olivose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-olivosylyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-rhamnose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
NDP-L-rhamnose + 8-demethyltetracenomycin C
NDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: when the elloramycin gene cluster is transformed into the mithramycin producer, Streptomyces argillaceus, four compounds are produced by the recombinant strain: the elloramycin aglycon 8-demethyl-tetracenomycin C and three glycosylated derivatives. Two of them contained a D-olivose or a D-mycarose moiety attached to the aglycon, 8-demethyl-8-beta-D-olivosyl-tetracenomycin C and 8-demethyl-8-beta-D-mycarosyl-tetracenomycin C. The third one contains a diolivosyl disaccharide attached to the aglycon, 8-demethyl-8-beta-D-diolivosyl-3'-1''-D-L-tetracenomycin C. The enzyme transfesr individually D-olivose and D-mycarose or a diolivosyl disaccharide to the aglycon 8-demethyl-tetracenomycin C
Products: -
Products: -
?
additional information
?
-
-
Substrates: when the elloramycin gene cluster is transformed into the mithramycin producer, Streptomyces argillaceus, four compounds are produced by the recombinant strain: the elloramycin aglycon 8-demethyl-tetracenomycin C and three glycosylated derivatives. Two of them contained a D-olivose or a D-mycarose moiety attached to the aglycon, 8-demethyl-8-beta-D-olivosyl-tetracenomycin C and 8-demethyl-8-beta-D-mycarosyl-tetracenomycin C. The third one contains a diolivosyl disaccharide attached to the aglycon, 8-demethyl-8-beta-D-diolivosyl-3'-1''-D-L-tetracenomycin C. The enzyme transfesr individually D-olivose and D-mycarose or a diolivosyl disaccharide to the aglycon 8-demethyl-tetracenomycin C
Products: -
Products: -
?
additional information
?
-
Substrates: when the elloramycin gene cluster is transformed into the mithramycin producer, Streptomyces argillaceus, four compounds are produced by the recombinant strain: the elloramycin aglycon 8-demethyl-tetracenomycin C and three glycosylated derivatives. Two of them contained a D-olivose or a D-mycarose moiety attached to the aglycon, 8-demethyl-8-beta-D-olivosyl-tetracenomycin C and 8-demethyl-8-beta-D-mycarosyl-tetracenomycin C. The third one contains a diolivosyl disaccharide attached to the aglycon, 8-demethyl-8-beta-D-diolivosyl-3'-1''-D-L-tetracenomycin C. The enzyme transfesr individually D-olivose and D-mycarose or a diolivosyl disaccharide to the aglycon 8-demethyl-tetracenomycin C
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: the enzyme is involved in biosynthesis of the antitumor polyketide elloramycin
Products: -
Products: -
?
dTDP-beta-L-rhamnose + 8-demethyltetracenomycin C
dTDP + 8-demethyl-8-alpha-L-rhamnosyltetracenomycin C
Substrates: the enzyme is involved in biosynthesis of the antitumor polyketide elloramycin
Products: -
Products: -
?
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
metabolism
the enzyme is involved in biosynthesis of the antitumor polyketide elloramycin
metabolism
-
the enzyme is involved in biosynthesis of the antitumor polyketide elloramycin
-
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A377ZT33_KLEPN
371
0
40097
TrEMBL
-
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
L309A
mutation in residue of the alpha/beta/alpha motif, results in 4fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
L309H
mutation in residue of the alpha/beta/alpha motif, results in decreases in the efficiency of deoxysugar transfer to 8-demethyltetracenomycin C
L309I
mutation in residue of the alpha/beta/alpha motif, results in 2fold increase in efficiency of L-rhamnose transfer to 8-demethyltetracenomycin C
L309M
mutation in residue of the alpha/beta/alpha motif, results in decreases in the efficiency of deoxysugar transfer to 8-demethyltetracenomycin C
L309Q
mutation in residue of the alpha/beta/alpha motif, results in decreases in the efficiency of deoxysugar transfer to 8-demethyltetracenomycin C
L309V
mutation in residue of the alpha/beta/alpha motif, results in 6fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
L309Y
mutation in residue of the alpha/beta/alpha motif, results in 2fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
N312Q
mutation in residue of the alpha/beta/alpha motif, results in 2fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
N312S
mutation in residue of the alpha/beta/alpha motif, results in 2fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
N312T
mutation in residue of the alpha/beta/alpha motif, results in 3fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
L309A
-
mutation in residue of the alpha/beta/alpha motif, results in 4fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
-
L309Q
-
mutation in residue of the alpha/beta/alpha motif, results in decreases in the efficiency of deoxysugar transfer to 8-demethyltetracenomycin C
-
L309V
-
mutation in residue of the alpha/beta/alpha motif, results in 6fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
-
L309Y
-
mutation in residue of the alpha/beta/alpha motif, results in 2fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
-
N312Q
-
mutation in residue of the alpha/beta/alpha motif, results in 2fold increase in efficiency of L-olivose transfer to 8-demethyltetracenomycin C
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
synthesis
medicine
generation of L- and D-stereoisomers of amicetose by combining sugar biosynthesis genes from four different antibiotic gene clusters and transfer of both sugars to the elloramycin aglycone by the sugar flexible ElmGT glycosyltransferase to yield antitumor tetracenomycins
medicine
-
generation of L- and D-stereoisomers of amicetose by combining sugar biosynthesis genes from four different antibiotic gene clusters and transfer of both sugars to the elloramycin aglycone by the sugar flexible ElmGT glycosyltransferase to yield antitumor tetracenomycins
-
synthesis
expression of NDP-glucose-synthase OleS, NDP-glucose-4, 6-dehydratase OleE, 2, 3-dehydratase OleV, 3, 5-epimerase OleL and 3-ketoreductase OleW in combination with elloramycin glycosyltransferase ElmGt in Streptomyces lividans results in accumulation of 8-demthyltetracenomycin C plus 8-demethyl-8-(4-dehydro)-alpha-L-olivosyl-tetracenomycin and 8-demethyl-8-alpha-L-olivosyl-tetracenomycin
synthesis
generation of L- and D-stereoisomers of amicetose by combining sugar biosynthesis genes from four different antibiotic gene clusters and transfer of both sugars to the elloramycin aglycone by the sugar flexible ElmGT glycosyltransferase to yield antitumor tetracenomycins
synthesis
-
expression of NDP-glucose-synthase OleS, NDP-glucose-4, 6-dehydratase OleE, 2, 3-dehydratase OleV, 3, 5-epimerase OleL and 3-ketoreductase OleW in combination with elloramycin glycosyltransferase ElmGt in Streptomyces lividans results in accumulation of 8-demthyltetracenomycin C plus 8-demethyl-8-(4-dehydro)-alpha-L-olivosyl-tetracenomycin and 8-demethyl-8-alpha-L-olivosyl-tetracenomycin
-
synthesis
-
generation of L- and D-stereoisomers of amicetose by combining sugar biosynthesis genes from four different antibiotic gene clusters and transfer of both sugars to the elloramycin aglycone by the sugar flexible ElmGT glycosyltransferase to yield antitumor tetracenomycins
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Blanco, G.; Patallo, E.P.; Brana, A.F.; Trefzer, A.; Bechthold, A.; Rohr, J.; Mendez, C.; Salas, J.A.
Identification of a sugar flexible glycosyltransferase from Streptomyces olivaceus, the producer of the antitumor polyketide elloramycin
Chem. Biol.
8
253-263
2001
Streptomyces olivaceus (Q9F2F9), Streptomyces olivaceus, Streptomyces olivaceus Tü2353 (Q9F2F9)
brenda
Ramos, A.; Olano, C.; Brana, A.F.; Mendez, C.; Salas, J.A.
Modulation of deoxysugar transfer by the elloramycin glycosyltransferase ElmGT through site-directed mutagenesis
J. Bacteriol.
191
2871-2875
2009
Streptomyces olivaceus (Q9F2F9), Streptomyces olivaceus, Streptomyces olivaceus Tü2353 (Q9F2F9)
brenda
Nybo, S.E.; Shabaan, K.A.; Kharel, M.K.; Sutardjo, H.; Salas, J.A.; Mendez, C.; Rohr, J.
Ketoolivosyl-tetracenomycin C: a new ketosugar bearing tetracenomycin reveals new insight into the substrate flexibility of glycosyltransferase ElmGT
Bioorg. Med. Chem. Lett.
22
2247-2250
2012
Streptomyces olivaceus (Q9F2F9), Streptomyces olivaceus Tü2353 (Q9F2F9)
brenda
Perez, M.; Lombo, F.; Zhu, L.; Gibson, M.; Brana, A.F.; Rohr, J.; Salas, J.A.; Mendez, C.
Combining sugar biosynthesis genes for the generation of L- and D-amicetose and formation of two novel antitumor tetracenomycins
Chem. Commun. (Camb. )
2005
1604-1606
2005
Streptomyces olivaceus (Q9F2F9), Streptomyces olivaceus Tü2353 (Q9F2F9)
brenda
Fischer, C.; Rodriguez, L.; Patallo, E.P.; Lipata, F.; Brana, A.F.; Mendez, C.; Salas, J.A.; Rohr, J.
Digitoxosyltetracenomycin C and glucosyltetracenomycin C, two novel elloramycin analogues obtained by exploring the sugar donor substrate specificity of glycosyltransferase ElmGT
J. Nat. Prod.
65
1685-1689
2002
Streptomyces olivaceus (Q9F2F9), Streptomyces olivaceus, Streptomyces olivaceus Tü2353 (Q9F2F9)
brenda
EXTERNAL LINKS (specific for EC-Number 2.4.1.331)
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