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Information on EC 2.4.99.25 - lipopolysaccharide heptosyltransferase III

for references in articles please use BRENDA:EC2.4.99.25

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EC Tree

2 Transferases

2.4 Glycosyltransferases

2.4.99 Transferring other glycosyl groups

2.4.99.25 lipopolysaccharide heptosyltransferase III

IUBMB Comments

The enzyme catalyses catalyses a glycosylation step in the biosynthesis of the inner core oligosaccharide of the lipopolysaccharide (endotoxin) of some Gram-negative bacteria.

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The enzyme appears in viruses and cellular organisms

Synonyms

heptosyltransferase iii, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

HepIII

Escherichia coli

P25742

761077

heptosyltransferase III

Salmonella enterica subsp. enterica serovar Typhimurium

rfaQ

WaaQ

rfaQ

rfaQ

Salmonella enterica subsp. enterica serovar Typhimurium

WaaQ

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

ADP-L-glycero-beta-D-manno-heptose + an alpha-Hep-(1->3)-4-O-phospho-alpha-Hep-(1->5)-[alpha-Kdo-(2->4)]-alpha-Kdo-(2->6)-[lipid A] = ADP + an alpha-Hep-(1->7)-alpha-Hep-(1->3)-4-O-phospho-alpha-Hep-(1->5)-[alpha-Kdo-(2->4)]-alpha-Kdo-(2->6)-[lipid A]

Lipid A is a lipid component of the lipopolysaccharides (LPS) of Gram-negative bacteria. It consists of two glucosamine units connected by a beta(1->6) bond and decorated with four to seven acyl chains and up to two phosphate groups. Hep = L-glycero-D-manno-heptose

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PATHWAY SOURCE

PATHWAYS

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SYSTEMATIC NAME

IUBMB Comments

ADP-L-glycero-beta-D-manno-heptose:an alpha-Hep-(1->3)-4-O-phospho-alpha-Hep-(1->5)-[alpha-Kdo-(2->4)]-alpha-Kdo-(2->6)-[lipid A] heptoseI 7-alpha-heptosyltransferase

The enzyme catalyses catalyses a glycosylation step in the biosynthesis of the inner core oligosaccharide of the lipopolysaccharide (endotoxin) of some Gram-negative bacteria.

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

ADP-L-glycero-beta-D-manno-heptose + alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-amino-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-2-amino-1-O-phosphono-alpha-D-glucopyranose

ADP + alpha-L-glycero-D-manno-heptosyl-(1->7)-alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-amino-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-2-amino-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

i.e. O-deacylated alpha-Kdo-(2->4)-[alpha-Hep-(1->3)-alpha-(4-O-phospho)-Hep-(1->5)]-alpha-Kdo-(2->6)-lipid A

761077

ADP-L-glycero-beta-D-manno-heptose + alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(hydroxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

ADP + alpha-L-glycero-D-manno-heptosyl-(1->7)-alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(hydroxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

i.e. O-deacylated alpha-Kdo-(2->4)-[alpha-Hep-(1->3)-alpha-(4-O-phospho)-Hep-(1->5)]-alpha-Kdo-(2->6)-lipid A

761077

ADP-L-glycero-beta-D-manno-heptose + alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

ADP + alpha-L-glycero-D-manno-heptosyl-(1->7)-alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

i.e. alpha-Kdo-(2->4)-[alpha-Hep-(1->3)-alpha-(4-O-phospho)-Hep-(1->5)]-alpha-Kdo-(2->6)-lipid A

761077

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

ADP-L-glycero-beta-D-manno-heptose + alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

ADP + alpha-L-glycero-D-manno-heptosyl-(1->7)-alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

i.e. alpha-Kdo-(2->4)-[alpha-Hep-(1->3)-alpha-(4-O-phospho)-Hep-(1->5)]-alpha-Kdo-(2->6)-lipid A

761077

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KM VALUE [mM]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.001

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

0.0006 - 0.0024

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-2-[[(3R)-3-(hydroxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

2 entries

0.006 - 0.01

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

2 entries

0.0006

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

0.0024

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5, 0.1% Triton X-100

761077

0.006

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5, 0.1% Triton X-100

761077

0.01

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

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TURNOVER NUMBER [1/s]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

0.07

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

0.019 - 0.028

2 entries

0.0049 - 0.041

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

2 entries

0.019

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5, 0.1% Triton X-100

761077

0.028

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

0.0049

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5, 0.1% Triton X-100

761077

0.041

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

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kcat/KM VALUE [1/mMs^-1]

SUBSTRATE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

IMAGE

6.7

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

4.6 - 7.9

2 entries

4.1 - 8.3

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

2 entries

4.6

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

7.9

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5, 0.1% Triton X-100

761077

4.1

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5

761077

8.3

alpha-L-glycero-D-manno-heptosyl-(1->3)-((4-O-phospho)-alpha-L-glycero-D-manno-heptosyl-(1->5))-[(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->4)]-(3-deoxy-alpha-D-manno-oct-2-ulopyranosylonate)-(2->6)-2-deoxy-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[[(3R)-3-(dodecanoyloxy)tetradecanoyl]amino]-4-O-phospho-beta-D-glucopyranosyl-(1->6)-2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[[(3R)-3-hydroxytetradecanoyl]amino]-1-O-phosphono-alpha-D-glucopyranose

Escherichia coli

P25742

37°C, 50 mM HEPES, 50 mM KCl, 10 mM MgCl2 and pH 7.5, 0.1% Triton X-100

761077

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Escherichia coli

761077

P25742

UniProt

brenda

Salmonella enterica subsp. enterica serovar Typhimurium

764991

H9L449

UniProt

brenda

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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).

H9L449 pBLAST

H9L449_SALTY

Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)

344

38715

TrEMBL

Show Sequence

P25742 pBLAST

RFAQ_ECOLI

Escherichia coli (strain K12)

344

38731

Swiss-Prot

Show Sequence

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CLONED (Commentary)

ORGANISM

UNIPROT

LITERATURE

Escherichia coli

P25742

761077

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

761077

Mudapaka, J.; Taylor, E.A.

Cloning and characterization of the Escherichia coli heptosyltransferase III Exploring substrate specificity in lipopolysaccharide core biosynthesis

FEBS Lett.

589

1423-1429

2015

Escherichia coli (P25742), Escherichia coli

25957775

brenda

764991

Sirisena, D.M.; MacLachlan, P.R.; Liu, S.L.; Hessel, A.; Sanderson, K.E.

Molecular analysis of the rfaD gene, for heptose synthesis, and the rfaF gene, for heptose transfer, in lipopolysaccharide synthesis in Salmonella typhimurium

J. Bacteriol.

176

2379-2385

1994

Salmonella enterica subsp. enterica serovar Typhimurium (H9L449)

8157607

brenda

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EXTERNAL LINKS (specific for EC-Number 2.4.99.25)

ExplorEnz (official portal for IUBMB Enzyme Nomenclature)

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KEGG

MetaCyc

SABIO-RK

NCBI: PubMed, Protein, Nucleotide, Structure, Gene, OMIM

Enzyme Nomenclature (alternative site)

UniProt

PDB

PROSITE Database of protein families and domains

InterPro (database of protein families, domains and functional sites)

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