Literature summary for 5.3.1.8 extracted from

Foret, J.; de Courcy, B.; Gresh, N.; Piquemal, J.P.; Salmon, L.
Synthesis and evaluation of non-hydrolyzable D-mannose 6-phosphate surrogates reveal 6-deoxy-6-dicarboxymethyl-D-mannose as a new strong inhibitor of phosphomannose isomerases (2009), Bioorg. Med. Chem., 17, 7100-7107.

Inhibitors

Inhibitors	Comment	Organism
5-deoxy-5-(dihydrogenophosphonomethyl)-D-arabinono-1,4-lactone	-	Escherichia coli
5-deoxy-5-(dihydrogenophosphonomethyl)-D-arabinono-1,4-lactone	-	Saccharomyces cerevisiae
5-deoxy-5-phosphonomethyl-D-arabinonate	-	Escherichia coli
5-deoxy-5-phosphonomethyl-D-arabinonate	-	Saccharomyces cerevisiae
5-deoxy-5-phosphonomethyl-D-arabinonohydrazide	-	Escherichia coli
5-deoxy-5-phosphonomethyl-D-arabinonohydrazide	-	Saccharomyces cerevisiae
5-deoxy-5-phosphonomethyl-D-arabinonohydroxamic acid	-	Escherichia coli
5-deoxy-5-phosphonomethyl-D-arabinonohydroxamic acid	-	Saccharomyces cerevisiae
6-deoxy-6-carboxymethyl-D-mannose	-	Escherichia coli
6-deoxy-6-carboxymethyl-D-mannose	-	Saccharomyces cerevisiae
6-deoxy-6-dicarboxymethyl-D-mannose	-	Escherichia coli
6-deoxy-6-dicarboxymethyl-D-mannose	-	Saccharomyces cerevisiae
6-deoxy-6-dimethylmalonate-D-mannopyranose	-	Escherichia coli
6-deoxy-6-dimethylmalonate-D-mannopyranose	-	Saccharomyces cerevisiae
6-deoxy-6-phosphonomethyl-D-mannose	-	Escherichia coli
6-deoxy-6-phosphonomethyl-D-mannose	-	Saccharomyces cerevisiae
benzyl 2,3,4-tri-O-benzyl-6-deoxy-6-dimethylmalonate-alpha-D-mannopyranoside	-	Escherichia coli
benzyl 2,3,4-tri-O-benzyl-6-deoxy-6-dimethylmalonate-alpha-D-mannopyranoside	-	Saccharomyces cerevisiae
benzyl 2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-alpha-D-mannose	-	Escherichia coli
benzyl 2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-alpha-D-mannose	-	Saccharomyces cerevisiae
benzyl 2,3,4-tri-O-benzyl-alpha-D-mannose	-	Escherichia coli
benzyl 2,3,4-tri-O-benzyl-alpha-D-mannose	-	Saccharomyces cerevisiae
additional information	synthesis of a non-hydrolyzable D-mannose 6-phosphate surrogates as strong competitive enzyme inhibitors. Effective binding to the catalytic site occurs with retention of the Zn(II)-bound water molecule. Molecular mechanics study of enzyme substrate and inhibitors, overview	Escherichia coli
additional information	synthesis of a non-hydrolyzable D-mannose 6-phosphate surrogates as strong competitive inhibitors of the enzyme. Effective binding to the catalytic site occurs with retention of the Zn(II)-bound water molecule. Molecular mechanics study of enzyme substrate and inhibitors, overview	Saccharomyces cerevisiae

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
D-Mannose 6-phosphate	Escherichia coli	-	D-Fructose 6-phosphate	-	r
D-Mannose 6-phosphate	Saccharomyces cerevisiae	-	D-Fructose 6-phosphate	-	r

Organism

Organism	UniProt	Comment	Textmining
Escherichia coli	-	-	-
Saccharomyces cerevisiae	-	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.
D-Mannose 6-phosphate	-	Escherichia coli	D-Fructose 6-phosphate	-	r
D-Mannose 6-phosphate	-	Saccharomyces cerevisiae	D-Fructose 6-phosphate	-	r
additional information	Molecular mechanics study of enzyme substrate and inhibitors, overview	Escherichia coli	?	-	?
additional information	Molecular mechanics study of enzyme substrate and inhibitors, overview	Saccharomyces cerevisiae	?	-	?

Synonyms

Synonyms	Comment	Organism
Phosphomannose isomerase	-	Escherichia coli
Phosphomannose isomerase	-	Saccharomyces cerevisiae

Temperature Optimum [°C]

Temperature Optimum [°C]	Temperature Optimum Maximum [°C]	Comment	Organism
25	-	assay at	Escherichia coli
25	-	assay at	Saccharomyces cerevisiae

pH Optimum

pH Optimum Minimum	pH Optimum Maximum	Comment	Organism
7.1	-	assay at	Escherichia coli
7.1	-	assay at	Saccharomyces cerevisiae

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
0.0105	-	6-deoxy-6-dicarboxymethyl-D-mannose	pH 7.1, 25°C, recombinant enzyme	Saccharomyces cerevisiae
0.115	-	6-deoxy-6-dicarboxymethyl-D-mannose	pH 7.1, 25°C, recombinant enzyme	Escherichia coli

IC50 Value

IC50 Value	IC50 Value Maximum	Comment	Organism	Inhibitor
0.0181	-	pH 7.1, 25°C, recombinant enzyme	Saccharomyces cerevisiae	6-deoxy-6-dicarboxymethyl-D-mannose
0.199	-	pH 7.1, 25°C, recombinant enzyme	Escherichia coli	6-deoxy-6-dicarboxymethyl-D-mannose
0.37	-	pH 7.1, 25°C, recombinant enzyme	Escherichia coli	5-deoxy-5-phosphonomethyl-D-arabinonohydroxamic acid
0.9	-	pH 7.1, 25°C, recombinant enzyme	Saccharomyces cerevisiae	6-deoxy-6-carboxymethyl-D-mannose
1.61	-	pH 7.1, 25°C, recombinant enzyme	Saccharomyces cerevisiae	6-deoxy-6-phosphonomethyl-D-mannose
2.2	-	pH 7.1, 25°C, recombinant enzyme	Saccharomyces cerevisiae	5-deoxy-5-phosphonomethyl-D-arabinonohydroxamic acid
3	-	above, pH 7.1, 25°C, recombinant enzyme	Escherichia coli	5-deoxy-5-phosphonomethyl-D-arabinonate
3	-	above, pH 7.1, 25°C, recombinant enzyme	Escherichia coli	5-deoxy-5-phosphonomethyl-D-arabinonohydrazide
4.6	-	pH 7.1, 25°C, recombinant enzyme	Escherichia coli	6-deoxy-6-carboxymethyl-D-mannose
4.7	-	pH 7.1, 25°C, recombinant enzyme	Escherichia coli	6-deoxy-6-phosphonomethyl-D-mannose