P. aeruginosa Metabolome Database: ADP-L-glycero-beta-D-manno-heptose (PAMDB006297)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB006297

Identification

Name:

ADP-L-glycero-beta-D-manno-heptose

Description:

ADP-L-glycero-beta-D-manno-heptose is an intermediate in pathway Lipid A-core biosynthesis in Pseudomonas aeruginosa. It is a substrate for enzymes ADP-heptose:Kdo2-lipid A heptosyltransferase, ADP-heptose:LPS heptosyltransferase, lipopolysaccharide core heptosyltransferase and lipid A-core heptosyltransferase. In pathway ADP-L-glycero-beta-D-manno-heptose biosynthesis, it is a product for enzyme ADP-L-glycero-D-mannoheptose-6-epimerase which catalyzes the reaction ADP-D-glycero-beta-D-manno-heptose -> ADP-L-glycero-beta-D-manno-heptose (PMID: 11751812; BioCyc compound: ADP-L-GLYCERO-D-MANNO-HEPTOSE).

Structure

Synonyms:

ADP-L-glycero-b-D-manno-Heptose
ADP-L-glycero-β-D-manno-Heptose

Chemical Formula:

C₁₇H₂₅N₅O₁₆P₂

Average Molecular Weight:

617.355

Monoisotopic Molecular Weight:

617.078250901

InChI Key:

KMSFWBYFWSKGGR-DTBZDYEHSA-L

InChI:

InChI=1S/C17H27N5O16P2/c18-14-7-15(20-3-19-14)22(4-21-7)16-11(28)8(25)6(35-16)2-34-39(30,31)38-40(32,33)37-17-12(29)9(26)10(27)13(36-17)5(24)1-23/h3-6,8-13,16-17,23-29H,1-2H2,(H,30,31)(H,32,33)(H2,18,19,20)/p-2/t5-,6+,8+,9-,10-,11+,12-,13+,16+,17-/m0/s1

CAS number:

Not Available

IUPAC Name:

Not Available

Traditional IUPAC Name:

Not Available

SMILES:

[H][C@](O)(CO)[C@@]1([H])O[C@@]([H])(OP([O-])(=O)OP([O-])(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)[C@@]([H])(O)[C@@]([H])(O)[C@]1([H])O

Chemical Taxonomy

Taxonomy Description

Not Available

Kingdom

Not Available

Super Class

Not Available

Class

Not Available

Sub Class

Not Available

Direct Parent

Not Available

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

Not Available

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

(KDO)2-lipid A + ADP-L-glycero-beta-D-manno-heptose > Hydrogen ion + Adenosine diphosphate + heptosyl-Kdo2-lipid A + ADP + Heptosyl-KDO2-lipid A
heptosyl-Kdo2-lipid A + ADP-L-glycero-beta-D-manno-heptose + Heptosyl-KDO2-lipid A > Adenosine diphosphate + Hydrogen ion + (heptosyl)2-Kdo2-lipid A + ADP
glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate + ADP-L-glycero-beta-D-manno-heptose > Adenosine diphosphate + Hydrogen ion + glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate + ADP
galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate + ADP-L-glycero-beta-D-manno-heptose > Hydrogen ion + Adenosine diphosphate + Lipid A-core + ADP
ADP-D-Glycero-D-manno-heptose > ADP-L-glycero-beta-D-manno-heptose

SMPDB Pathways:

ADP-L-glycero-Beta-D-manno-heptose biosynthesis	PW002095
Lipopolysaccharide biosynthesis	PW000831
lipopolysaccharide biosynthesis II	PW001905
lipopolysaccharide biosynthesis III	PW002059

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

Pathways:

Lipopolysaccharide biosynthesis pae00540

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02t9-2310009000-e08331368a76b0a7fc70	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-6390078000-3fee374441206d63e4df	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08or-9300000000-33b4c2d3e436e4603bb6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02t9-4400009000-066591ed925c27928056	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-9310004000-713a81ebf0ff40f77b0d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bt9-9300000000-77c87b51685dad4d82e3	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link

Enzymes

Protein Details

• ADP-L-glycero-D-manno-heptose-6-epimerase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the interconversion between ADP-D-glycero- beta-D-manno-heptose and ADP-L-glycero-beta-D-manno-heptose via an epimerization at carbon 6 of the heptose
Gene Name:: hldD
Locus Tag:: PA3337
Molecular weight:: 37.4 kDa

Reactions

ADP-D-glycero-D-manno-heptose = ADP-L-glycero-D-manno-heptose.

Protein Details

• Lipopolysaccharide heptosyltransferase 1

General function:: Involved in transferase activity, transferring glycosyl groups
Specific function:: Heptose transfer to the lipopolysaccharide core. It transfers the innnermost heptose to [4'-P](3-deoxy-D-manno- octulosonic acid)2-IVA
Gene Name:: rfaC
Locus Tag:: PA5011
Molecular weight:: 39.7 kDa