Escherichia coli K-12 substr. MG1655 Compound Class: GDP-L-fucose

Synonyms: guanosine diphosphate fucose, guanosine 5'-(trihydrogen diphosphate), P'-(6-deoxy-β-L- galactopyranosyl) ester, 2-amino-9-[3,4-dihydroxy-5-[[hydroxy-[hydroxy-(3,4,5-trihydroxy- 6-methyl-tetrahydropyran-2-yl)oxy-phosphinoyl]oxy-phosphinoyl] oxymethyl]tetrahydrofuran-2-yl]-1,9-dihydropurin-6-one

Superclasses: a nucleic acid componenta base derivativea nucleotide sugaran NDP-sugara GDP-sugar
a nucleic acid componenta GDP-sugar
all carbohydratesa carbohydratea glycana carbohydrate derivativea nucleotide sugaran NDP-sugara GDP-sugar

GDP-L-fucose compound structure

Chemical Formula: C16H23N5O15P2


Molecular Weight: 587.33 Daltons

Monoisotopic Molecular Weight: 589.08223818 Daltons

SMILES: CC4(OC(OP(OP(OCC3(C(C(C(N2(C1(=C(C(NC(=N1)N)=O)N=C2)))O3)O)O))([O-])=O)([O-])=O)C(C(C4O)O)O)

Unification Links: CAS:15839-70-0, HMDB:HMDB01095, KEGG:C00325

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -227.4 [Forsythe97]

In Reactions of unknown directionality:

Not in pathways:
GDP-L-fucose + UDP-D-glucose + UDP-α-D-glucuronate + UDP-α-D-galactose = colanic acid

Enzymes inhibited by GDP-L-fucose, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: GDP-mannose 4,6-dehydratase [Somoza00, Comment 1], GDP-fucose synthase [Menon99]


Forsythe97: Forsythe RG, Karp PD, Mavrovouniotis ML (1997). "Estimation of Equilibrium Constants Using Automated Group Contribution Methods." CABIOS 13(5):537-543.

Menon99: Menon S, Stahl M, Kumar R, Xu GY, Sullivan F (1999). "Stereochemical course and steady state mechanism of the reaction catalyzed by the GDP-fucose synthetase from Escherichia coli." J Biol Chem 274(38);26743-50. PMID: 10480878

Somoza00: Somoza JR, Menon S, Schmidt H, Joseph-McCarthy D, Dessen A, Stahl ML, Somers WS, Sullivan FX (2000). "Structural and kinetic analysis of Escherichia coli GDP-mannose 4,6 dehydratase provides insights into the enzyme's catalytic mechanism and regulation by GDP-fucose." Structure Fold Des 2000;8(2);123-35. PMID: 10673432

Sturla97: Sturla L, Bisso A, Zanardi D, Benatti U, De Flora A, Tonetti M (1997). "Expression, purification and characterization of GDP-D-mannose 4,6-dehydratase from Escherichia coli." FEBS Lett 1997;412(1);126-30. PMID: 9257704

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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