Common Name2-c-methyl-d-erythritol 4-phosphate
Description2-c-methyl-D-erythritol-4-phosphate is a member of the chemical class known as Tetroses. These are tetrasaccharides whose saccharide units are all hexoses. 2-C-methyl-D-erythritol-4-phosphate is involved in isoprenoid biosynthesis. Using genetically engineered Escherichia coli cells able to utilize exogenously provided mevalonate for isoprenoid biosynthesis by the mevalonate pathway we demonstrate that the lytB gene is involved in the trunk line of the MEP pathway. (PMID 11418107 ) The first step of the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway for isoprenoid biosynthesis in plant plastids and most eubacteria is catalyzed by 1-deoxy-D-xylulose 5-phosphate synthase (DXS), a recently described transketolase-like enzyme. (PMID 11708793 ) In the MEP pathway, 4-diphosphocytidyl-2-C-methyl-D-erythritol is formed from 2-C-methyl-D-erythritol 4-phosphate (MEP) and CTP in a reaction catalyzed by a 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase (IspD). (PMID 17921290 ) (E)-4-Hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE), which catalyzes the conversion of 2-C-methyl-D-erythritol cyclodiphosphate (MEcPP) into (E)-4-hydroxy-3-methylbut-2-enyl diphosphate (HMBPP), is an essential enzyme of the non-mevalonate (2-C-methyl-D-erythritol-4-phosphate (MEP)) pathway for isoprenoid biosynthesis. (E)-4-Hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE), which catalyzes the conversion of 2-C-methyl-D-erythritol cyclodiphosphate (MEcPP) into (E)-4-hydroxy-3-methylbut-2-enyl diphosphate (HMBPP), is an essential enzyme of the non-mevalonate (2-C-methyl-D-erythritol-4-phosphate (MEP)) pathway for isoprenoid biosynthesis. (PMID 15792953 ) Escherichia coli AmtB is a member of the MEP/Amt family of ammonia transporters found in archaea, eubacteria, fungi, plants and animals. (PMID 12753193 )
Structure
Molecular FormulaC5H11O7P
Average Mass214.11040
Monoisotopic Mass214.02424
IUPAC Name2-methyl-4-(phosphonatooxy)butane-1,2,3-triol
Traditional Name2-methyl-4-(phosphonatooxy)butane-1,2,3-triol
CAS Registry NumberNot Available
SMILESC[C@](O)(CO)[C@H](O)COP(=O)([O-])[O-]
InChI IdentifierInChI=1S/C5H13O7P/c1-5(8,3-6)4(7)2-12-13(9,10)11/h4,6-8H,2-3H2,1H3,(H2,9,10,11)/p-2
InChI KeyXMWHRVNVKDKBRG-UHFFFAOYSA-L
CHEBI IDCHEBI:58262
StateNot Available
Water Solubility6.93e+01 g/l
logP-1.71
logS-0.56
pKa (Strongest Acidic)Not Available
pKa (Strongest Basic)Not Available
Hydrogen Acceptor Count6
Hydrogen Donor Count3
Polar Surface Area133.11 Ų
Rotatable Bond Count5
Physiological ChargeNot Available
Formal Charge-2
Refractivity39.75 m³·mol⁻¹
Polarizability17.46

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