ECMDB: ADP-Glucose (ECMDB06557) (M2MDB000683)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (680)

Record Information

Version

2.0

Creation Date

2012-05-31 14:09:02 -0600

Update Date

2015-06-03 15:54:53 -0600

Secondary Accession Numbers

ECMDB06557

Identification

Name:

ADP-Glucose

Description

ADP-glucose serves as the glycosyl donor for formation of bacterial glycogen, amylose in green algae, and amylopectin in higher plants. It is an intermediate in starch and sucrose metabolism and involved in amino sugar and nucleotide sugar metabolism. (KEGG)

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

Adenosine 5'-(trihydrogen diphosphate) glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphate) p'-a-delta-glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphate) p'-a-δ-glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphate) P'-alpha-delta-glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphate) p'-α-δ-glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphoric acid) glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphoric acid) p'-a-delta-glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphoric acid) p'-a-δ-glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphoric acid) p'-alpha-delta-glucopyranosyl ester
Adenosine 5'-(trihydrogen diphosphoric acid) p'-α-δ-glucopyranosyl ester
Adenosine 5'-(trihydrogen pyrophosphate) mono-D-glucosyl ester
Adenosine 5'-(trihydrogen pyrophosphate) mono-delta-glucosyl ester
Adenosine 5'-(trihydrogen pyrophosphate) mono-δ-glucosyl ester
Adenosine 5'-(trihydrogen pyrophosphoric acid) mono-D-glucosyl ester
Adenosine 5'-(trihydrogen pyrophosphoric acid) mono-delta-glucosyl ester
Adenosine 5'-(trihydrogen pyrophosphoric acid) mono-δ-glucosyl ester
Adenosine 5'-diphosphoglucose
Adenosine 5'-pyrophosphate a-D-glucosyl ester
Adenosine 5'-pyrophosphate a-delta-glucosyl ester
Adenosine 5'-pyrophosphate a-δ-glucosyl ester
Adenosine 5'-pyrophosphate alpha-D-glucosyl ester
Adenosine 5'-pyrophosphate alpha-delta-glucosyl ester
Adenosine 5'-pyrophosphate glucosyl ester
Adenosine 5'-pyrophosphate mono-D-glucosyl ester
Adenosine 5'-pyrophosphate mono-delta-glucosyl ester
Adenosine 5'-pyrophosphate mono-δ-glucosyl ester
Adenosine 5'-pyrophosphate α-D-glucosyl ester
Adenosine 5'-pyrophosphate α-δ-glucosyl ester
Adenosine 5'-pyrophosphoric acid a-D-glucosyl ester
Adenosine 5'-pyrophosphoric acid a-delta-glucosyl ester
Adenosine 5'-pyrophosphoric acid a-δ-glucosyl ester
Adenosine 5'-pyrophosphoric acid alpha-D-glucosyl ester
Adenosine 5'-pyrophosphoric acid alpha-delta-glucosyl ester
Adenosine 5'-pyrophosphoric acid glucosyl ester
Adenosine 5'-pyrophosphoric acid mono-D-glucosyl ester
Adenosine 5'-pyrophosphoric acid mono-delta-glucosyl ester
Adenosine 5'-pyrophosphoric acid mono-δ-glucosyl ester
Adenosine 5'-pyrophosphoric acid α-D-glucosyl ester
Adenosine 5'-pyrophosphoric acid α-δ-glucosyl ester
Adenosine diphosphate D-glucose
Adenosine diphosphate glucose
Adenosine diphosphoglucose
Adenosine diphosphoric acid D-glucose
Adenosine diphosphoric acid glucose
Adenosine pyrophosphate-glucose
Adenosine pyrophosphoric acid-glucose
Adenosine-5'-diphosphate-glucose
Adenosine-5'-diphosphoric acid-glucose
ADP-D-Glucose
ADP-Glc
ADP-Glucose
ADP-α-D-glucose

Chemical Formula:

C₁₆H₂₅N₅O₁₅P₂

Weight:

Average: 589.3417
Monoisotopic: 589.082238179

InChI Key:

WFPZSXYXPSUOPY-ROYWQJLOSA-N

InChI:

InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/t5-,6-,8-,9-,10+,11-,12-,15-,16-/m1/s1

CAS number:

2140-58-1

IUPAC Name:

[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional IUPAC Name:

adp glucose

SMILES:

NC1=C2N=CN([C@@H]3O[C@H](CO[P@](O)(=O)O[P@](O)(=O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H]3O)C2=NC=N1

Chemical Taxonomy

Description

belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine nucleotide sugars

Alternative Parents

Substituents

Purine nucleotide sugar
Purine ribonucleoside diphosphate
Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Imidolactam
Alkyl phosphate
Pyrimidine
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Azacycle
Polyol
Oxacycle
Organic oxide
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Amine
Organonitrogen compound
Primary alcohol
Primary amine
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alpha-D-glucoside (CHEBI:15751 )
ADP-aldose (CHEBI:15751 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	4.84 g/L	ALOGPS
logP	-1.8	ALOGPS
logP	-6.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	3.99	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	311.75 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	117.09 m³·mol⁻¹	ChemAxon
Polarizability	48.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

ADP-Glucose > ADP + Glycogen + Hydrogen ion
Adenosine triphosphate + Glucose 1-phosphate + Hydrogen ion <> ADP-Glucose + Pyrophosphate
Adenosine triphosphate + Glucose 1-phosphate <> Pyrophosphate + ADP-Glucose
ADP-Glucose + 1,4-alpha-D-glucan <> ADP + 1,4-alpha-D-glucan
Hydrogen ion + Glucose 1-phosphate + Adenosine triphosphate > ADP-Glucose + Pyrophosphate
a 1,4-α-D-glucan + ADP-Glucose <> ADP + a 1,4-α-D-glucan
ADP-Glucose + (1,4-alpha-D-glucosyl)(n) > ADP + (1,4-alpha-D-glucosyl)(n+1)
Adenosine triphosphate + Alpha-D-glucose 1-phosphate > Pyrophosphate + ADP-Glucose
Alpha-D-glucose 1-phosphate + Adenosine triphosphate > ADP-Glucose + Pyrophosphate
Alpha-D-glucose 1-phosphate + Adenosine triphosphate + Hydrogen ion > ADP-Glucose + Pyrophosphate
ADP-Glucose + Amylose <> Amylose + Adenosine diphosphate + ADP

SMPDB Pathways:

Amino sugar and nucleotide sugar metabolism II	PW000887
Amino sugar and nucleotide sugar metabolism III	PW000895
Secondary metabolites: Trehalose Biosynthesis and Metabolism	PW000968
Starch and sucrose metabolism	PW000941

KEGG Pathways:

Amino sugar and nucleotide sugar metabolism ec00520
Metabolic pathways eco01100
Starch and sucrose metabolism ec00500

EcoCyc Pathways:

glycogen biosynthesis I (from ADP-D-Glucose) GLYCOGENSYNTH-PWY

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
4± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05di-5941580000-aa3b11c510a971dd2bae	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05be-8925707000-bdd8b43e72abaa64441b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("ADP-glucose,1TMS,#1" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, positive	splash10-0006-0000290000-7f66f6e8af24e4839d36	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-004l-0000950000-739c8280d86a2f6f3b3b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative	splash10-002k-9248080000-875881d0c025c30eb244	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - NA , negative	splash10-003r-3900000000-64717800131918b409d1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1901000000-e41db8583774d0cca66d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0000940000-0f0b4d7b3da79f054155	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000900000-c6a92771658ee7a74bb5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0401900000-e9c970aa89843c279822	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0910520000-894488255e0d2059a6ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0910000000-af7d8977d3d229ea73ee	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-39c6318a5ada8cb3ebb4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001r-1901470000-134113735239a2586876	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1901000000-48fb3c4c1d3e3f084d3d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0563-3900000000-f9f285dafe2da95e8009	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000090000-494b86dfa2b4e6fc0ac1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0570-5421970000-431fd452ea842be1eb27	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2922610000-bc7320a1bf5a6bf0dc76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000090000-46811e8e339262e18415	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-0841490000-f709931b7e24d70dc4f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2921000000-17d11c3948611bf9ff8b	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Baroja-Fernandez E, Etxeberria E, Munoz FJ, Moran-Zorzano MT, Alonso-Casajus N, Gonzalez P, Pozueta-Romero J: An important pool of sucrose linked to starch biosynthesis is taken up by endocytosis in heterotrophic cells. Plant Cell Physiol. 2006 Apr;47(4):447-56. Epub 2006 Jan 24. Pubmed: 16434435
Baroja-Fernandez E, Munoz FJ, Montero M, Etxeberria E, Sesma MT, Ovecka M, Bahaji A, Ezquer I, Li J, Prat S, Pozueta-Romero J: Enhancing sucrose synthase activity in transgenic potato (Solanum tuberosum L.) tubers results in increased levels of starch, ADPglucose and UDPglucose and total yield. Plant Cell Physiol. 2009 Sep;50(9):1651-62. doi: 10.1093/pcp/pcp108. Epub 2009 Jul 16. Pubmed: 19608713
Bejar CM, Ballicora MA, Iglesias AA, Preiss J: ADPglucose pyrophosphorylase's N-terminus: structural role in allosteric regulation. Biochem Biophys Res Commun. 2006 Apr 28;343(1):216-21. Epub 2006 Mar 2. Pubmed: 16530732
Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Comparot-Moss S, Denyer K: The evolution of the starch biosynthetic pathway in cereals and other grasses. J Exp Bot. 2009;60(9):2481-92. doi: 10.1093/jxb/erp141. Pubmed: 19505928
Eydallin G, Moran-Zorzano MT, Munoz FJ, Baroja-Fernandez E, Montero M, Alonso-Casajus N, Viale AM, Pozueta-Romero J: An Escherichia coli mutant producing a truncated inactive form of GlgC synthesizes glycogen: further evidences for the occurrence of various important sources of ADPglucose in enterobacteria. FEBS Lett. 2007 Sep 18;581(23):4417-22. Epub 2007 Aug 15. Pubmed: 17719034
Ezquer I, Li J, Ovecka M, Baroja-Fernandez E, Munoz FJ, Montero M, Diaz de Cerio J, Hidalgo M, Sesma MT, Bahaji A, Etxeberria E, Pozueta-Romero J: A suggested model for potato MIVOISAP involving functions of central carbohydrate and amino acid metabolism, as well as actin cytoskeleton and endocytosis. Plant Signal Behav. 2010 Dec;5(12):1638-41. Epub 2010 Dec 1. Pubmed: 21150257
Ezquer I, Li J, Ovecka M, Baroja-Fernandez E, Munoz FJ, Montero M, Diaz de Cerio J, Hidalgo M, Sesma MT, Bahaji A, Etxeberria E, Pozueta-Romero J: Microbial volatile emissions promote accumulation of exceptionally high levels of starch in leaves in mono- and dicotyledonous plants. Plant Cell Physiol. 2010 Oct;51(10):1674-93. doi: 10.1093/pcp/pcq126. Epub 2010 Aug 24. Pubmed: 20739303
Fettke J, Malinova I, Albrecht T, Hejazi M, Steup M: Glucose-1-phosphate transport into protoplasts and chloroplasts from leaves of Arabidopsis. Plant Physiol. 2011 Apr;155(4):1723-34. doi: 10.1104/pp.110.168716. Epub 2010 Nov 29. Pubmed: 21115809
Haferkamp I: The diverse members of the mitochondrial carrier family in plants. FEBS Lett. 2007 May 25;581(12):2375-9. Epub 2007 Feb 26. Pubmed: 17321523
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Li J, Baroja-Fernandez E, Bahaji A, Munoz FJ, Ovecka M, Montero M, Sesma MT, Alonso-Casajus N, Almagro G, Sanchez-Lopez AM, Hidalgo M, Zamarbide M, Pozueta-Romero J: Enhancing sucrose synthase activity results in increased levels of starch and ADP-glucose in maize (Zea mays L.) seed endosperms. Plant Cell Physiol. 2013 Feb;54(2):282-94. doi: 10.1093/pcp/pcs180. Epub 2013 Jan 3. Pubmed: 23292602
Lunn JE, Feil R, Hendriks JH, Gibon Y, Morcuende R, Osuna D, Scheible WR, Carillo P, Hajirezaei MR, Stitt M: Sugar-induced increases in trehalose 6-phosphate are correlated with redox activation of ADPglucose pyrophosphorylase and higher rates of starch synthesis in Arabidopsis thaliana. Biochem J. 2006 Jul 1;397(1):139-48. Pubmed: 16551270
Moran-Zorzano MT, Alonso-Casajus N, Munoz FJ, Viale AM, Baroja-Fernandez E, Eydallin G, Pozueta-Romero J: Occurrence of more than one important source of ADPglucose linked to glycogen biosynthesis in Escherichia coli and Salmonella. FEBS Lett. 2007 Sep 18;581(23):4423-9. Epub 2007 Aug 15. Pubmed: 17719035
Nagai YS, Sakulsingharoj C, Edwards GE, Satoh H, Greene TW, Blakeslee B, Okita TW: Control of starch synthesis in cereals: metabolite analysis of transgenic rice expressing an up-regulated cytoplasmic ADP-glucose pyrophosphorylase in developing seeds. Plant Cell Physiol. 2009 Mar;50(3):635-43. doi: 10.1093/pcp/pcp021. Epub 2009 Feb 10. Pubmed: 19208694
Smith AM: Prospects for increasing starch and sucrose yields for bioethanol production. Plant J. 2008 May;54(4):546-58. doi: 10.1111/j.1365-313X.2008.03468.x. Pubmed: 18476862
Szecowka M, Osorio S, Obata T, Araujo WL, Rohrmann J, Nunes-Nesi A, Fernie AR: Decreasing the mitochondrial synthesis of malate in potato tubers does not affect plastidial starch synthesis, suggesting that the physiological regulation of ADPglucose pyrophosphorylase is context dependent. Plant Physiol. 2012 Dec;160(4):2227-38. doi: 10.1104/pp.112.204826. Epub 2012 Oct 12. Pubmed: 23064409
Thorneycroft D, Hosein F, Thangavelu M, Clark J, Vizir I, Burrell MM, Ainsworth C: Characterization of a gene from chromosome 1B encoding the large subunit of ADPglucose pyrophosphorylase from wheat: evolutionary divergence and differential expression of Agp2 genes between leaves and developing endosperm. Plant Biotechnol J. 2003 Jul;1(4):259-70. Pubmed: 17163903
Tiessen A, Nerlich A, Faix B, Hummer C, Fox S, Trafford K, Weber H, Weschke W, Geigenberger P: Subcellular analysis of starch metabolism in developing barley seeds using a non-aqueous fractionation method. J Exp Bot. 2012 Mar;63(5):2071-87. doi: 10.1093/jxb/err408. Epub 2011 Dec 26. Pubmed: 22200665
Uhlmann NK, Beckles DM: Storage products and transcriptional analysis of the endosperm of cultivated wheat and two wild wheat species. J Appl Genet. 2010;51(4):431-47. doi: 10.1007/BF03208873. Pubmed: 21063061
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Wiedemuth K, Muller J, Kahlau A, Amme S, Mock HP, Grzam A, Hell R, Egle K, Beschow H, Humbeck K: Successive maturation and senescence of individual leaves during barley whole plant ontogeny reveals temporal and spatial regulation of photosynthetic function in conjunction with C and N metabolism. J Plant Physiol. 2005 Nov;162(11):1226-36. Pubmed: 16323274
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Tamura, Kiminori; Morozumi, Manami; Yoshino, Hiroshi; Noda, Yutaka; Suzuki, Morio. Nucleotide anhydrides. Ger. Offen. (1972), 16 pp. CODEN: GWXXBX DE 2038262 19720203 CAN 76:99993 AN 1972:99993

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	15751
HMDB ID	HMDB06557
Pubchem Compound ID	16500
Kegg ID	C00498
ChemSpider ID	15642
Wikipedia ID	Not Available
BioCyc ID	ADP-D-GLUCOSE
EcoCyc ID	ADP-D-GLUCOSE
Ligand Expo	ADQ

Enzymes

Protein Details

1. Glycogen synthase

General function:: Involved in biosynthetic process
Specific function:: Synthesizes alpha-1,4-glucan chains using ADP-glucose
Gene Name:: glgA
Uniprot ID:: P0A6U8
Molecular weight:: 52822

Reactions

ADP-glucose + (1,4-alpha-D-glucosyl)(n) = ADP + (1,4-alpha-D-glucosyl)(n+1).

Protein Details

2. Glucose-1-phosphate adenylyltransferase

General function:: Involved in glycogen biosynthetic process
Specific function:: ATP + alpha-D-glucose 1-phosphate = diphosphate + ADP-glucose
Gene Name:: glgC
Uniprot ID:: P0A6V1
Molecular weight:: 48697

Reactions

ATP + alpha-D-glucose 1-phosphate = diphosphate + ADP-glucose.

ADP-Glucose (ECMDB06557) (M2MDB000683)

Structure for #<Compound:0xad771034>

Enzymes

Reactions

Reactions