Uridine diphosphate N-acetylglucosamine

From Wikipedia, the free encyclopedia

Uridine diphosphate N-acetylglucosamine
Names

IUPAC name Uridine 5′-(2-acetamido-2-deoxy-α-D-glucopyranosyl dihydrogen diphosphate)
Systematic IUPAC name O¹-[(2R,3R,4R,5S,6R)-3-Acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] O³-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} dihydrogen diphosphate
Other names UDP-N-acetylglucosamine; UDP-GlcNAc
Identifiers
CAS Number	91183-98-1^N
3D model (JSmol)	Interactive image
IUPHAR/BPS	1779
PubChem CID	445675
CompTox Dashboard (EPA)	DTXSID10912327
SMILES CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
Properties
Chemical formula	C₁₇H₂₇N₃O₁₇P₂
Molar mass	607.355 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Uridine diphosphate N-acetylglucosamine or UDP-GlcNAc is a nucleotide sugar and a coenzyme in metabolism. It is used by glycosyltransferases to transfer N-acetylglucosamine residues to substrates. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars.^[1] To be specific, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine^[2] as the first step of the hexosamine biosynthesis pathway.^[3] The end-product of this pathway is UDP-GlcNAc, which is then used for making glycosaminoglycans, proteoglycans, and glycolipids.^[4]

UDP-GlcNAc is extensively involved in intracellular signaling as a substrate for O-linked N-acetylglucosamine transferases (OGTs) to install the O-GlcNAc post-translational modification in a wide range of species. It is also involved in nuclear pore formation and nuclear signalling. OGTs and OG-ases play an important role in the structure of the cytoskeleton. In mammals, there is enrichment of OGT transcripts in the pancreas beta-cells, and UDP-GlcNAc is thought to be part of the glucose sensing mechanism. There is also evidence that it plays a part in insulin sensitivity in other cells. In plants, it is involved in the control of gibberellin production.^[5]

Clostridium novyi type A alpha-toxin is an O-linked N-actetylglucosamine transferase acting on Rho proteins and causing the collapse of the cytoskeleton.

References

^ Roseman S (2001). "Reflections on glycobiology". The Journal of Biological Chemistry. 276 (45): 41527–42. doi:10.1074/jbc.R100053200. PMID 11553646.
^ Sudhamoy Ghosh, Blumenthal HJ, Davidson E, Roseman S (1960-05-01). "Glucosamine Metabolism". Journal of Biological Chemistry. 235 (5): 1265–73. doi:10.1016/S0021-9258(18)69397-4. PMID 13827775.
^ International Union of Biochemistry and Molecular Biology
^ Milewski S, Gabriel I, Olchowy J (2006). "Enzymes of UDP-GlcNAc biosynthesis in yeast". Yeast. 23 (1): 1–14. doi:10.1002/yea.1337. PMID 16408321.
^ Hanover JA (2001). "Glycan-dependent signaling: O-linked N-acetylglucosamine". The FASEB Journal. 15 (11): 1865–1876. CiteSeerX 10.1.1.324.6370. doi:10.1096/fj.01-0094rev. PMID 11532966.

v t e Types of nucleotide sugars
CDP-glucose GDP-mannose TDP-glucose UDP-glucose UDP-galactose UDP-glucuronic acid UDP-N-acetylglucosamine

Purine receptor modulators

Receptor
(ligands)

P0 (adenine)

Agonists: 8-Aminoadenine
Adenine

P1
(adenosine)

Agonists: 2-(1-Hexynyl)-N-methyladenosine
2-Cl-IB-MECA
2-Chloroadenosine
2'-MeCCPA
4'-O-β-D-Glucosyl-9-O-(6''-deoxysaccharosyl)olivil
5'-N-ethylcarboxamidoadenosine
Adenosine
ADP
AMP
Apadenoson
ATL-146e
ATP
BAY 60–6583
Binodenoson
Capadenoson
CCPA
CGS-21680
CP-532,903
CV-1808
Evodenoson
GR 79236
HENECA
LUF-5835
LUF-5845
N⁶-Cyclopentyladenosine
Namodenoson
NECA
Neladenoson dalanate
Piclidenoson
Regadenoson
SDZ WAG 994
Selodenoson
Sonedenoson
Tecadenoson
Trabodenoson
UK-432,097

Antagonists: 3-Chlorostyrylcaffeine (CSC)
7-Methylxanthine
8-Chlorotheophylline
8-Phenyl-1,3-dipropylxanthine
8-Phenyltheophylline
Acefylline
Aminophylline
ATL-444
AZD-4635
Bamifylline
Cafedrine
Caffeine
Caffeine citrate
Cartazolate
CGH-2466
CGS-15943
Choline theophyllinate
Ciforadenant
CPX
CVT-6883
Dimethazan
DMPX
DPCPX
Dyphylline
Enprofylline
Etazolate
Etrumadenant
Fenethylline
IBMX
Imaradenant
Inupadenant
ISAM-140
ISAM-R316
Isovaleric acid
Istradefylline
KF-26777
Lu AA41063
Lu AA47070
MRE3008F20
MRS-1191
MRS-1220
MRS-1334
MRS-1523
MRS-1706
MRS-1754
MRS-3777
MSX-2
MSX-3
MSX-4
Muvadenant
Paraxanthine
Pentoxifylline
Preladenant
Propentofylline
Proxyphylline
PSB-10
PSB-11
PSB-36
PSB-603
PSB-788
PSB-1115
PSB-1901
Reversine
Rolofylline
SCH-442,416
SCH-58261
Sipagladenant
Taminadenant
Theacrine
Theobromine
Theodrenaline
Theophylline
Tozadenant
Tracazolate
Vipadenant
VUF-5574
ZM-241,385

P2
(nucleotide)

P2X
(ATP)

Antagonists: 5-BDBD
A-317491
A-438079
A-740003
A-804598
A-839977
AF-353
AZ-10606120
AZ-11645373
BBG
Calcium
Calmidazolium
Chelerythrine
Copper
Emodin (Rheum officinale)
Evans blue
Gefapixant
GW-791343
HMA
Ip5I
isoPPADS
JNJ-47965567
KN-04
KN-62
Magnesium
MRS-2159
NF-023
NF-110
NF-157
NF-279
NF-449
Opiranserin (VVZ-149)
Oxidized-ATP
Phenol Red
Phenolphthalein
PPADS
PPNDS
PSB-12062
Puerarin (Radix puerariae)
Purotoxin 1
RB-2
Ro 0437626
Ro 51
RO-3
Sodium ferulate (Angelica sinensis, Ligusticum wallichii)
Suramin
TC-P 262
Tetramethylpyrazine (ligustrazine) (Ligusticum wallichii)
TNP-ATP
Zinc

P2Y

Transporter
(blockers)

CNTsTooltip Concentrative nucleoside transporters	6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone
ENTsTooltip Equilibrative nucleoside transporters	Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline
PMATTooltip Plasma membrane monoamine transporter	Decynium-22

Enzyme
(inhibitors)

XOTooltip Xanthine oxidase	Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxipurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat
Others	Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others

Others

Others: Chrysophanol (rhubarb)

See also: Receptor/signaling modulators

Categories:

Hidden categories: