1.0 2011-09-21 00:26:32 UTC 2015-07-21 06:57:35 UTC FDB023223 Glutamylalanine Glutamylalanine is a naturally occurring dipeptide. Glutamylalanine is essential in the supply of glutamate to human erythrocytes. Human erythrocytes are essentially impermeable to glutamate and yet there is a continual requirement for the amino acid for glutathione synthesis. In addition, the intracellular glutamate concentration is approximately five times that of plasma. Glutamylalanine enters the human erythrocyte through saturable membrane-transport systems describable by Michaelis- Menten kinetics. The cytosolic red cell peptidases have a vast capacity to hydrolyse the dipeptide in a process also describable by simple Michaelis-Menten kinetics. The transport process is the rate-determining step in the pathway leading to the production of intracellular glutamate from extracellular glutamylalanine. Glutamylalanine is transported by the human oligopeptide transporter, hPepT1, situated in the small intestine, which is involved in the absorption of nutrient oligopeptides and transports numerous di- and tripeptides. This active transport is being tested for use as a strategy to increase the permeability across the intestine for larger biologically active molecules with low intestinal permeability, in a therapeutic attempt to transport dipeptide-coupled active drug substances via hPepT1. (PMID: 2860897, 11557350) [HMDB] a-Glutamylalanine a-L-Glutamyl-L-alanine alpha-Glutamylalanine alpha-L-Glutamyl-L-alanine Glu-ala L-alpha-Glutamyl-L-amino acid L-Glutamyl-L-alanine n-l-alpha-glutamyl-L-alanine C8H14N2O5 218.2072 218.090271568 4-amino-4-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]butanoic acid glu-ala 21064-18-6 CC(NC(=O)C(N)CCC(O)=O)C(O)=O InChI=1S/C8H14N2O5/c1-4(8(14)15)10-7(13)5(9)2-3-6(11)12/h4-5H,2-3,9H2,1H3,(H,10,13)(H,11,12)(H,14,15) JZDHUJAFXGNDSB-UHFFFAOYSA-N belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Dipeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Alanine and derivatives Alpha amino acid amides Amino acids Amino fatty acids Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Glutamic acid and derivatives Hydrocarbon derivatives Monoalkylamines N-acyl amines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Secondary carboxylic acid amides Alanine or derivatives Aliphatic acyclic compound Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-dipeptide Amine Amino acid Amino acid or derivatives Amino fatty acid Carbonyl group Carboxamide group Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Fatty acyl Fatty amide Glutamic acid or derivatives Hydrocarbon derivative N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary carboxylic acid amide Solid logp -3.31 ALOGPS logs -1.62 ALOGPS solubility 5.28e+00 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 3.1 ChemAxon pka_strongest_basic 9.62 ChemAxon iupac 4-amino-4-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]butanoic acid ChemAxon average_mass 218.2072 ChemAxon mono_mass 218.090271568 ChemAxon smiles CC(NC(=O)C(N)CCC(O)=O)C(O)=O ChemAxon formula C8H14N2O5 ChemAxon inchi InChI=1S/C8H14N2O5/c1-4(8(14)15)10-7(13)5(9)2-3-6(11)12/h4-5H,2-3,9H2,1H3,(H,10,13)(H,11,12)(H,14,15) ChemAxon inchikey JZDHUJAFXGNDSB-UHFFFAOYSA-N ChemAxon polar_surface_area 133.21 ChemAxon refractivity 49.11 ChemAxon polarizability 20.97 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 103077 Specdb::MsMs 103078 Specdb::MsMs 103079 Specdb::MsMs 169020 Specdb::MsMs 169021 Specdb::MsMs 169022 Specdb::CMs 24890 Specdb::CMs 38651 HMDB03764 #<Reference:0x000055ce3066c958> #<Reference:0x000055ce3066c728> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823