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Revision as of 10:51, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Saving copy of the {{chembox}} taken from revid 444228533 of page Thymidine_diphosphate_glucose for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').		Latest revision as of 20:34, 7 May 2023 edit LegionMammal978 (talk | contribs)Extended confirmed users7,894 edits add semisystematic name
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{Chembox		{{Chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 444227537
			| Watchedfields = changed
		⚫	| verifiedrevid = 477863841
	| ImageFile = Thymidine diphosphate glucose.png		| ImageFile = Thymidine diphosphate glucose.png
	| ImageSize = 200px		| ImageSize =
			| IUPACName = Thymidine 5′-(α-<small>D</small>-glucopyranosyl trihydrogen diphosphate)
	| IUPACName = <nowiki>methoxy-oxidophosphoryl] hydrogen phosphate		| SystematicName = ''O''<sup>1</sup>-<nowiki/>{methyl} ''O''<sup>3</sup>- dihydrogen diphosphate
	| OtherNames = TDP-glucose; dTDP-glucose		| OtherNames = TDP-glucose; dTDP-glucose
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|changed|??}}
	| CASNo = <!-- blanked - oldvalue: 2196-62-5 -->
			| CASNo = 2196-62-5
		⚫	| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 412989		| ChEMBL = 412989
	| PubChem = 25202390		| PubChem = 25202390
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	| ChEBI = 15700		| ChEBI = 15700
	| SMILES = CC1=CN(C(=O)NC1=O)2C((O2)COP(=O)(O)OP(=O)(O)O3((((O3)CO)O)O)O)O		| SMILES = CC1=CN(C(=O)NC1=O)2C((O2)COP(=O)(O)OP(=O)(O)O3((((O3)CO)O)O)O)O
	| ChEMBL = 412989		| PubChem2 = 443210
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| PubChem = 443210
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 391476		| ChemSpiderID = 391476
		⚫	| SMILES2 = O=C1\C(=C/N(C(=O)N1)2O((O)C2)COP(=O)(O)OP(=O)(O)O3O((O)(O)3O)CO)C
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| ChEBI = 15700
		⚫	| StdInChI = 1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15+/m0/s1
⚫	| SMILES = O=C1\C(=C/N(C(=O)N1)2O((O)C2)COP(=O)(O)OP(=O)(O)O3O((O)(O)3O)CO)C
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫	| StdInChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15+/m0/s1
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = YSYKRGRSMLTJNL-URARBOGNSA-N		| StdInChIKey = YSYKRGRSMLTJNL-URARBOGNSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=16|H=26|N=2|O=16|P=2		| C=16 | H=26 | N=2 | O=16 | P=2
	| Appearance =		| Appearance =
	| Density =		| Density =
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	| BoilingPt =		| BoilingPt =
	| Solubility = }}		| Solubility = }}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
	| Autoignition = }}		| AutoignitionPt =
			}}
	}}		}}
			'''Thymidine diphosphate glucose''' (often abbreviated '''dTDP-glucose''' or '''TDP-glucose''') is a nucleotide-linked sugar consisting of ] linked to ]. It is the starting compound for the syntheses of many ]s.<ref name="Liu">{{cite journal |doi=10.1146/annurev.biochem.71.110601.135339 |author=Xue M. He |author2=Hung-wen Liu |name-list-style=amp|title=Formation of unusual sugars: Mechanistic studies and biosynthetic applications |journal=Annu Rev Biochem |volume=71 |pages=701–754 |year= 2002 |pmid=12045109}}</ref>
			==Biosynthesis==
			DTDP-glucose is produced by the enzyme ] and is synthesized from ] and ]. ] is a byproduct of the reaction.
			==Uses within the cell==
			DTDP-glucose goes on to form a variety of compounds in ]. Many bacteria utilize dTDP-glucose to form exotic sugars that are incorporated into their ]s or into ] such as ]. During the syntheses of many of these exotic sugars, dTDP-glucose undergoes a combined oxidation/reduction reaction via the enzyme ], producing dTDP-4-keto-6-deoxy-glucose.<ref name="Liu"/><ref name="Reeves">{{cite journal |vauthors=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>
			==References==
			{{reflist}}
			{{Nucleotide sugars}}
			]
			]
			]