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Cytidine diphosphate glucose: Difference between revisions

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{{Chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400127872
| ImageFile = Cytidine diphosphate glucose.png | ImageFile = Cytidine diphosphate glucose.png
| IUPACName = Cytidine 5′-(α-<small>D</small>-glucopyranosyl trihydrogen diphosphate)
| ImageSize = 200px
| IUPACName = <nowiki>methoxy-hydroxyphosphoryl] hydrogen | SystematicName = ''O''<sup>1</sup>-<nowiki/>{methyl} ''O''<sup>3</sup>- dihydrogen diphosphate
phosphate
| OtherNames = CDP-glucose | OtherNames = CDP-glucose
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 2906-23-2 | CASNo = 2906-23-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = C3MET5N4NR
| PubChem = 439244 | PubChem = 439244
| SMILES = C1=CN(C(=O)N=C1N)2(((O2)COP(=O)(O)OP(=O)(O)O3((((O3)CO)O)O)O)O)O | SMILES = C1=CN(C(=O)N=C1N)2(((O2)COP(=O)(O)OP(=O)(O)O3((((O3)CO)O)O)O)O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ }}
| ChemSpiderID = 388381
⚫ | Section2 = {{Chembox Properties
| SMILES2 = O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC3O(N2/C=C\C(=N/C2=O)\N)(O)3O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = CGPHZDRCVSLMCF-JZMIEXBBSA-N
⚫ }}
⚫ |Section2={{Chembox Properties
| C=15|H=25|N=3|O=16|P=2 | C=15|H=25|N=3|O=16|P=2
| Appearance = | Appearance =
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| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility =
}}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| AutoignitionPt =
| Autoignition = }}
}}
}} }}


'''Cytidine diphosphate glucose''', often abbreviated '''CDP-glucose''', is a nucleotide-linked sugar consisting of cytidine diphospahte and glucose.<ref name="Reeves">{{cite journal |author=Samuel G, Reeves P |title=Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly |journal=Carbohydr. Res. |volume=338 |issue=23 |pages=2503–19 |year=2003 |pmid=14670712 |doi=10.1016/j.carres.2003.07.009}}</ref><ref name="Liu">{{cite journal |doi=10.1146/annurev.biochem.71.110601.135339 |author=Xue M. He and Hung-wen Liu|title=Formation of unusual sugars: Mechanistic studies and biosynthetic applications |journal=Annu Rev Biochem |volume=71 |issue= |pages=701–754 |year= 2002 |pmid=12045109}}</ref> '''Cytidine diphosphate glucose''', often abbreviated '''CDP-glucose''', is a ] consisting of ] and ].<ref name="Reeves">{{cite journal |author=Samuel G, Reeves P |title=Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly |journal=Carbohydr. Res. |volume=338 |issue=23 |pages=2503–19 |year=2003 |pmid=14670712 |doi=10.1016/j.carres.2003.07.009}}</ref><ref name="Liu">{{cite journal |doi=10.1146/annurev.biochem.71.110601.135339 |author=Xue M. He and Hung-wen Liu|title=Formation of unusual sugars: Mechanistic studies and biosynthetic applications |journal=Annu Rev Biochem |volume=71 |pages=701–754 |year= 2002 |pmid=12045109}}</ref> This nucleotide saccharide participates in the synthesis of ] such as ] and ].<ref name=":0" />


==Biosynthesis== ==Metabolism==


CDP-glucose is produced from ] and ] by the enzyme ]. CDP-glucose is produced from ] and ] by the enzyme ].<ref name=":0">{{Cite journal |last1=Koropatkin |first1=Nicole M. |last2=Cleland |first2=W. Wallace |last3=Holden |first3=Hazel M. |date=March 2005 |title=Kinetic and Structural Analysis of α-d-Glucose-1-phosphate Cytidylyltransferase from Salmonella typhi |journal=Journal of Biological Chemistry |volume=280 |issue=11 |pages=10774–10780 |doi=10.1074/jbc.m414111200 |doi-access=free |issn=0021-9258}}</ref>

CDP-glucose is an important metabolite in certain bacteria, which synthesize ] from it.<ref name=":0" /> CDP-glucose can also be used as a substrate for ], along its native substrate, ]. The same is true for ].<ref>{{Cite journal |last1=Alonso |first1=Miriam D. |last2=Lagzdins |first2=Erik J. |last3=Lomako |first3=Joseph |last4=Lomako |first4=Wieslawa M. |last5=Whelan |first5=William J. |date=1995-02-13 |title=New and specific nucleoside diphosphate glucose substrates for glycogenin |url=https://febs.onlinelibrary.wiley.com/doi/10.1016/0014-5793%2895%2900018-5 |journal=FEBS Letters |language=en |volume=359 |issue=2–3 |pages=110–112 |doi=10.1016/0014-5793(95)00018-5 |bibcode=1995FEBSL.359..110A |issn=0014-5793}}</ref>


==References== ==References==
{{reflist}} {{reflist}}



{{Nucleotide sugars}} {{Nucleotide sugars}}


] ]
] ]
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