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Identification
YMDB IDYMDB00277
NameUridine diphosphate-N-acetylglucosamine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionUridine diphosphate-N-acetylglucosamine, also known as UDP-N-acetyl-D-glucosamine or UDP-glcnac, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphate-N-acetylglucosamine is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate-N-acetylglucosamine exists in all living species, ranging from bacteria to humans. Within yeast, uridine diphosphate-N-acetylglucosamine participates in a number of enzymatic reactions. In particular, dolichol phosphate and uridine diphosphate-N-acetylglucosamine can be converted into uridine 5'-monophosphate and N-acetyl-α-D-glucosaminyl-diphosphodolichol; which is catalyzed by the enzyme UDP-N-acetylglucosamine--dolichyl-phosphate N-acetylglucosaminephosphotransferase. In addition, N-acetyl-α-D-glucosaminyl-diphosphodolichol and uridine diphosphate-N-acetylglucosamine can be converted into (N-acetylglucosaminyl)2-diphosphodolichol and UDP ; which is catalyzed by the enzyme N-acetylglucosaminyldiphosphodolichol N-acetylglucosaminyltransferase. In yeast, uridine diphosphate-N-acetylglucosamine is involved in the metabolic pathway called n-glycan biosynthesis pathway.
Structure
Thumb
Synonyms
  • [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinate
  • [[3-acetylamino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxy-phosphoryl]oxy-[[5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy]phosphinic acid
  • N-[2-[[[5-[(2,4-dioxo-1H-pyrimidin-1-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]acetamide
  • UDP-a-D-N-acetylglucosamine
  • UDP-acetyl-D-glucosamine
  • UDP-acetyl-delta-glucosamine
  • UDP-acetylglucosamine
  • UDP-alpha-D-N-acetylglucosamine
  • UDP-alpha-delta-N-acetylglucosamine
  • UDP-GlcNAc
  • UDP-N-acetyl-D-glucosamine
  • UDP-N-acetyl-delta-glucosamine
  • UDP-N-acetyl-glucosamine
  • UDP-N-acetylglucosamine
  • UPPAG
  • Uridine 5'-Diphospho-N-Acetlyglucosamine
  • Uridine 5'-diphospho-N-acetylglucosamine
  • Uridine diphosphate N-acetyl-D-glucosamine
  • Uridine diphosphate N-acetyl-delta-glucosamine
  • Uridine diphosphate N-acetylglucosamine
  • Uridine diphospho-2-acetamido-2-deoxy-D-glucose
  • Uridine diphospho-2-acetamido-2-deoxy-delta-glucose
  • Uridine diphospho-N-acetyl-D-glucosamine
  • Uridine diphospho-N-acetyl-delta-glucosamine
  • Uridine diphospho-N-acetylglucosamine
  • uridine diphosphoacetylglucosamine
  • Uridine pyrophosphate 2-acetamido-2-deoxy-a-D-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-D-glucopyranosyl ester
  • Uridine pyrophosphate 2-acetamido-2-deoxy-alpha-delta-glucopyranosyl ester
  • Uridine pyrophosphoacetylglucosamine
  • (2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphate (non-preferred name)
  • URIDINE-diphosphATE-N-acetylglucosamine
  • (2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name)
  • URIDINE-diphosphoric acid-N-acetylglucosamine
  • Uridine diphosphoric acid-N-acetylglucosamine
  • Acetylglucosamine, UDP
  • Diphosphate N-acetylglucosamine, uridine
  • Diphospho-N-acetylglucosamine, uridine
  • N-Acetylglucosamine, uridine diphosphate
  • Pyrophosphoacetylglucosamine, uridine
  • UDP Acetylglucosamine
  • UDPGNAc
  • Uridine diphosphate N acetylglucosamine
  • Uridine diphospho N acetylglucosamine
CAS number528-04-1
WeightAverage: 607.3537
Monoisotopic: 607.081569477
InChI KeyLFTYTUAZOPRMMI-CFRASDGPSA-N
InChIInChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
IUPAC Name[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Nameudp-N-acetyl-α-D-glucosamine
Chemical FormulaC17H27N3O17P2
SMILES[H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]2([H])O[C@@]([H])(N3C([H])=C([H])C(=O)N([H])C3=O)[C@]([H])(O[H])[C@]2([H])O[H])[C@]([H])(N([H])C(=O)C([H])([H])[H])[C@@]([H])(O[H])[C@]1([H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-acyl-alpha-hexosamine
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pyrimidone
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Vinylogous amide
  • Acetamide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Urea
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.4 g/LALOGPS
logP-1.4ALOGPS
logP-5.3ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area300.41 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.56 m³·mol⁻¹ChemAxon
Polarizability50.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
N-Glycan biosynthesisPW002501 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
N-Glycan biosynthesisec00510 Map00510
SMPDB Reactions
N-Acetyl-glucosamine 1-phosphate + Uridine triphosphate + hydronPyrophosphate + Uridine diphosphate-N-acetylglucosamine
Uridine diphosphate-N-acetylglucosamine + ChitinUridine 5'-diphosphate + Chitin
Dolichol phosphate + Uridine diphosphate-N-acetylglucosamineUridine 5'-monophosphate + N-acetyl-α-D-glucosaminyl-diphosphodolichol
N-acetyl-α-D-glucosaminyl-diphosphodolichol + Uridine diphosphate-N-acetylglucosamine (N-Acetylglucosaminyl)2-diphosphodolichol + Uridine 5'-diphosphate + hydron
KEGG Reactions
Uridine diphosphate-N-acetylglucosamine → chitin + Uridine 5'-diphosphate + hydron
Uridine triphosphate + N-acetyl-alpha-D-glucosamine 1-phosphate + hydronPyrophosphate + Uridine diphosphate-N-acetylglucosamine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (n TMS)splash10-00di-9620000000-18841b4db9b69a91db36JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9620000000-18841b4db9b69a91db36JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-5924660000-c11cc7fa21a050c0f373JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03di-5501619000-8584f57aecb61fc3e5b6JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0a4i-5543009000-8a176d160a1f074ab319JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negativesplash10-05cr-4796000000-6c09aa3a2dac66281973JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0a4i-5543009000-8a176d160a1f074ab319JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-05cr-4796000000-6c09aa3a2dac66281973JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910020000-b4f448790a5adc1b2231JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3921000000-b1ea97b129b6c701887eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5910000000-af36b4483c7d5529ce86JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01pc-9801421000-87db24d9515a2033d9b0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01po-9605020000-323a53bc8a8e293636d7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-5911000000-aee8e2f7d665fa10b3b1JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Milewski, S., Gabriel, I., Olchowy, J. (2006). "Enzymes of UDP-GlcNAc biosynthesis in yeast." Yeast 23:1-14.16408321
Synthesis Reference:Takenouchi, Kenji; Ishige, Kazuya; Midorikawa, Yuichiro; Okuyama, Kiyoshi; Hamamoto, Tomoki; Noguchi, Toshitada. Process for producing uridine diphosphate-N-acetylglucosamine. PCT Int. Appl. (1999), 38 pp.
External Links:
ResourceLink
CHEBI ID16264
HMDB IDHMDB00290
Pubchem Compound ID10705
Kegg IDC00043
ChemSpider ID393240
FOODB IDFDB021930
WikipediaUridine_diphosphate_N-acetylglucosamine
BioCyc IDUDP-N-ACETYL-D-GLUCOSAMINE

Enzymes

General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
Catalyzes the initial step in the synthesis of dolichol- P-P-oligosaccharides
Gene Name:
ALG7
Uniprot ID:
P07286
Molecular weight:
50367.39844
Reactions
UDP-N-acetyl-D-glucosamine + dolichyl phosphate → UMP + N-acetyl-D-glucosaminyl-diphosphodolichol.
General function:
Involved in UDP-N-acetylglucosamine diphosphorylase act
Specific function:
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate = diphosphate + UDP-N-acetyl-D-glucosamine
Gene Name:
QRI1
Uniprot ID:
P43123
Molecular weight:
53475.60156
Reactions
UTP + N-acetyl-alpha-D-glucosamine 1-phosphate → diphosphate + UDP-N-acetyl-D-glucosamine.
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Involved in protein N-glycosylation. Essential for the second step of the dolichol-linked oligosaccharide pathway
Gene Name:
ALG13
Uniprot ID:
P53178
Molecular weight:
22660.90039
Reactions
UDP-N-acetyl-D-glucosamine + N-acetyl-D-glucosaminyl-diphosphodolichol → UDP + N,N'-diacetylchitobiosyl-diphosphodolichol.
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltr
Specific function:
Part of the complex catalyzing the transfer of N- acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis. Involved in cell wall biosynthesis
Gene Name:
GPI19
Uniprot ID:
Q04082
Molecular weight:
16089.40039
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N- acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis
Gene Name:
GPI1
Uniprot ID:
P53306
Molecular weight:
70353.70313
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
General function:
Involved in biosynthetic process
Specific function:
Catalytic subunit in the complex catalyzing the transfer of N-acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis
Gene Name:
SPT14
Uniprot ID:
P32363
Molecular weight:
51241.80078
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N- acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis
Gene Name:
GPI2
Uniprot ID:
P46961
Molecular weight:
32576.80078
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.
General function:
Involved in chitin synthase activity
Specific function:
Essential for septum formation and cell division. CHS2 is required for maintaining normal cell morphology
Gene Name:
CHS2
Uniprot ID:
P14180
Molecular weight:
109881.0
Reactions
UDP-N-acetyl-D-glucosamine + (1,4-(N-acetyl-beta-D-glucosaminyl))(n) → UDP + (1,4-(N-acetyl-beta-D-glucosaminyl))(n+1).
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Appears to be responsible for the synthesis of the majority of the chitin found in the cell wall periphery. It is involved in the synthesis of the chitin ring that forms in the cell wall just before bud emergence. This ring remains at the base of the bud as the bud grows and ultimately forms part of the bud scar marking the division site on the mother cell
Gene Name:
CHS3
Uniprot ID:
P29465
Molecular weight:
131600.0
Reactions
UDP-N-acetyl-D-glucosamine + (1,4-(N-acetyl-beta-D-glucosaminyl))(n) → UDP + (1,4-(N-acetyl-beta-D-glucosaminyl))(n+1).
General function:
Involved in chitin synthase activity
Specific function:
Septum formation and repair, especially under certain adverse conditions
Gene Name:
CHS1
Uniprot ID:
P08004
Molecular weight:
129918.0
Reactions
UDP-N-acetyl-D-glucosamine + (1,4-(N-acetyl-beta-D-glucosaminyl))(n) → UDP + (1,4-(N-acetyl-beta-D-glucosaminyl))(n+1).
General function:
Involved in phosphatidylinositol N-acetylglucosaminyltransferase activity
Specific function:
Part of the complex catalyzing the transfer of N- acetylglucosamine from UDP-N-acetylglucosamine to phosphatidylinositol, the first step of GPI biosynthesis
Gene Name:
GPI15
Uniprot ID:
P53961
Molecular weight:
26816.5
Reactions
UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol → UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol.