L-Aspartic acid (PAMDB000080)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 1/22/2018 11:54:54 AM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Metabolite ID | PAMDB000080 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Aspartic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description: | Aspartic acid (Asp, D), also known as aspartate (the name of its anion), is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins. Aspartic acid has 2 enantiomeric forms: D and L. L-aspartic acid is the isomer with more biological roles and is the form used in constructing proteins. (Wikipedia) In Pseudomonas aeruginosa, L-aspartate can be produced from L-glutamate, and interconversion can occur between L-asparagine and L-aspartate. L-aspartate is also involved in the biosynthesis pathways of many compounds, including adenosine nucleotides, beta-alanine, and homoserine. (EcoCyc) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |
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| Synonyms: |
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| Chemical Formula: | C4H7NO4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight: | 133.1027 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight: | 133.037507717 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | CKLJMWTZIZZHCS-REOHCLBHSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C4H7NO4/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H,6,7)(H,8,9)/t2-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 56-84-8 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2-aminobutanedioic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-aspartic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | N[C@@H](CC(O)=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Taxonomy Description | This compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | D-alpha-amino acids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 270 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
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| Predicted Properties |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | L-Aspartic acid + Carbamoylphosphate <> Ureidosuccinic acid + Hydrogen ion + Phosphate L-Aspartic acid + Adenosine triphosphate <> L-Aspartyl-4-phosphate + ADP Adenosine triphosphate + Water + L-Aspartic acid > ADP + L-Aspartic acid + Hydrogen ion + Phosphate Adenosine triphosphate + Water + L-Aspartic acid > ADP + L-Aspartic acid + Hydrogen ion + Phosphate L-Asparagine + Water > L-Aspartic acid + Ammonium L-Aspartic acid + Hydrogen ion <> beta-Alanine + Carbon dioxide L-Aspartic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + L-Asparagine + L-Glutamate + Hydrogen ion + Pyrophosphate alpha-Ketoglutarate + L-Aspartic acid <> L-Glutamate + Oxalacetic acid L-Aspartic acid + Adenosine triphosphate + tRNA(Asp) + tRNA(Asp) <> Adenosine monophosphate + L-Aspartyl-tRNA(Asp) + Pyrophosphate + L-Aspartyl-tRNA(Asp) 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate L-Aspartic acid + Fumaric acid > Hydrogen ion + Iminoaspartic acid + Succinic acid L-Aspartic acid + Oxygen <> Hydrogen ion + Hydrogen peroxide + Iminoaspartic acid L-Aspartic acid + Ubiquinone-8 > Hydrogen ion + Iminoaspartic acid + Ubiquinol-8 L-Aspartic acid + Menaquinone 8 > Hydrogen ion + Iminoaspartic acid + Menaquinol 8 L-Aspartic acid + Adenosine triphosphate + Citrulline <> Adenosine monophosphate + Argininosuccinic acid + Hydrogen ion + Pyrophosphate L-Aspartic acid + Adenosine triphosphate + Ammonium > Adenosine monophosphate + L-Asparagine + Hydrogen ion + Pyrophosphate L-Aspartic acid > Fumaric acid + Ammonium L-Aspartic acid + Guanosine triphosphate + Inosinic acid <> Adenylsuccinic acid + Guanosine diphosphate +2 Hydrogen ion + Phosphate L-Aspartic acid + Water + Oxygen <> Oxalacetic acid + Ammonia + Hydrogen peroxide L-Aspartic acid + Oxygen <> Iminoaspartic acid + Hydrogen peroxide Adenosine triphosphate + L-Aspartic acid + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine L-Asparagine + Water <> L-Aspartic acid + Ammonia L-Aspartic acid <> beta-Alanine + Carbon dioxide More...L-Aspartic acid <> Fumaric acid + Ammonia Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate Guanosine triphosphate + Inosinic acid + L-Aspartic acid <> Guanosine diphosphate + Phosphate + Adenylsuccinic acid Carbamoylphosphate + L-Aspartic acid <> Phosphate + Ureidosuccinic acid Adenosine triphosphate + Citrulline + L-Aspartic acid <> Adenosine monophosphate + Pyrophosphate + Argininosuccinic acid Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid <> ADP + Phosphate + SAICAR tRNA(Asp) + L-Aspartic acid + Adenosine triphosphate <> L-Aspartyl-tRNA(Asp) + Pyrophosphate + Adenosine monophosphate a dipetide with aspartate at N-terminal + Water L-Aspartic acid + a standard α amino acid L-Aspartic acid + Inosinic acid + Guanosine triphosphate > Hydrogen ion + adenylo-succinate + Phosphate + Guanosine diphosphate L-Aspartic acid + Citrulline + Adenosine triphosphate > Hydrogen ion + L-arginino-succinate + Pyrophosphate + Adenosine monophosphate L-Aspartic acid + Oxoglutaric acid <> Oxalacetic acid + L-Glutamate L-Asparagine + Water > Hydrogen ion + L-Aspartic acid + Ammonia L-Aspartic acid <> Hydrogen ion + Fumaric acid + Ammonia Pyridoxamine + Oxalacetic acid <> Pyridoxal + L-Aspartic acid ala-asp + Water > L-Alanine + L-Aspartic acid gly-asp + Water > Glycine + L-Aspartic acid -->-->Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > ADP + Inorganic phosphate + SAICAR Carbamoylphosphate + L-Aspartic acid > Inorganic phosphate + Ureidosuccinic acid Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > Adenosine diphosphate + L-Aspartyl-4-phosphate + ADP Adenosine triphosphate + L-Aspartic acid + Ammonia + L-Aspartic acid > Adenosine monophosphate + L-Asparagine + Pyrophosphate + L-Asparagine Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + L-Aspartic acid > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid + L-Asparagine + L-Glutamate L-Aspartic acid + Oxoglutaric acid + L-Aspartic acid > Oxalacetic acid + L-Glutamic acid + L-Glutamate L-Aspartic acid + Water + Oxygen + L-Aspartic acid > Oxalacetic acid + Ammonia + Hydrogen peroxide L-Aspartic acid + Oxygen + L-Aspartic acid > Hydrogen peroxide + Hydrogen ion + Iminoaspartic acid L-Aspartic acid + L-Aspartic acid > Fumaric acid + Ammonia L-Aspartic acid + L-Aspartic acid > Fumaric acid + Ammonium Guanosine triphosphate + Inosinic acid + L-Aspartic acid + L-Aspartic acid > Guanosine diphosphate + Phosphate + N(6)-(1,2-dicarboxyethyl)AMP Inosinic acid + L-Aspartic acid + Guanosine triphosphate + L-Aspartic acid > Guanosine diphosphate + Phosphate +2 Hydrogen ion + N(6)-(1,2-dicarboxyethyl)AMP + Adenylsuccinic acid Adenosine triphosphate + Citrulline + L-Aspartic acid + L-Aspartic acid > Pyrophosphate + Adenosine monophosphate + Argininosuccinic acid L-Aspartic acid + L-Aspartic acid > N-carbamoyl-L-aspartate L-Aspartic acid + Adenosine triphosphate + Hydrogen ion + tRNA(Asp) + L-Aspartic acid > Pyrophosphate + Adenosine monophosphate + L-aspartyl-tRNA(Asp) L-Aspartic acid + Water + Adenosine triphosphate + L-Glutamine + L-Aspartic acid > L-Asparagine + Hydrogen ion + Adenosine monophosphate + L-Glutamic acid + Pyrophosphate + L-Asparagine + L-Glutamate L-Aspartic acid + Adenosine triphosphate + Ammonium + L-Aspartic acid > L-Asparagine + Adenosine monophosphate + Pyrophosphate + Hydrogen ion + L-Asparagine L-Aspartic acid + Hydrogen ion + L-Aspartic acid Carbon dioxide + beta-Alanine L-Asparagine + Water + L-Asparagine > L-Aspartic acid + Ammonium + L-Aspartic acid 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > SAICAR + Phosphate + Adenosine diphosphate + Hydrogen ion + SAICAR + ADP Carbamoylphosphate + L-Aspartic acid + L-Aspartic acid > Phosphate + Hydrogen ion + N-carbamoyl-L-aspartate L-Aspartic acid + Adenosine triphosphate + Water + L-Aspartic acid > Adenosine diphosphate + Phosphate + Hydrogen ion + L-Aspartic acid + ADP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Pathways: |
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| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
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| Synthesis Reference: | Pamfil, Maria; Lupescu, Irina; Savoiu, Valeria Gabriela. L-aspartic acid production from fumarate using Escherichia coli whole cells. Rom. (2005), 3pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
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Enzymes
- General function:
- Involved in asparaginase activity
- Specific function:
- L-asparagine + H(2)O = L-aspartate + NH(3)
- Gene Name:
- ansB
- Locus Tag:
- PA1337
- Molecular weight:
- 38.6 kDa
Reactions
| L-asparagine + H(2)O = L-aspartate + NH(3). |
- General function:
- Involved in transferase activity
- Specific function:
- An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate
- Gene Name:
- tyrB
- Locus Tag:
- PA3139
- Molecular weight:
- 43.3 kDa
Reactions
| An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate. |
- General function:
- Involved in amino acid binding
- Specific function:
- ATP + L-aspartate = ADP + 4-phospho-L- aspartate
- Gene Name:
- lysC
- Locus Tag:
- PA0904
- Molecular weight:
- 44.4 kDa
Reactions
| ATP + L-aspartate = ADP + 4-phospho-L-aspartate. |
- General function:
- Involved in argininosuccinate synthase activity
- Specific function:
- ATP + L-citrulline + L-aspartate = AMP + diphosphate + N(omega)-(L-arginino)succinate
- Gene Name:
- argG
- Locus Tag:
- PA3525
- Molecular weight:
- 45.3 kDa
Reactions
| ATP + L-citrulline + L-aspartate = AMP + diphosphate + N(omega)-(L-arginino)succinate. |
- General function:
- Involved in carboxyl- or carbamoyltransferase activity
- Specific function:
- Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate
- Gene Name:
- pyrB
- Locus Tag:
- PA0402
- Molecular weight:
- 36.6 kDa
Reactions
| Carbamoyl phosphate + L-aspartate = phosphate + N-carbamoyl-L-aspartate. |
- General function:
- Involved in aspartate 1-decarboxylase activity
- Specific function:
- Catalyzes the pyruvoyl-dependent decarboxylation of aspartate to produce beta-alanine
- Gene Name:
- panD
- Locus Tag:
- PA4731
- Molecular weight:
- 13.9 kDa
Reactions
| L-aspartate = beta-alanine + CO(2). |
- General function:
- Involved in adenylosuccinate synthase activity
- Specific function:
- Plays an important role in the de novo pathway of purine nucleotide biosynthesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP
- Gene Name:
- purA
- Locus Tag:
- PA4938
- Molecular weight:
- 46.8 kDa
Reactions
| GTP + IMP + L-aspartate = GDP + phosphate + N(6)-(1,2-dicarboxyethyl)-AMP. |
- General function:
- Involved in ATP binding
- Specific function:
- ATP + 5-amino-1-(5-phospho-D- ribosyl)imidazole-4-carboxylate + L-aspartate = ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxamido)succinate
- Gene Name:
- purC
- Locus Tag:
- PA1013
- Molecular weight:
- 26.8 kDa
Reactions
| ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate. |
- General function:
- Involved in asparaginase activity
- Specific function:
- L-asparagine + H(2)O = L-aspartate + NH(3)
- Gene Name:
- ansA
- Locus Tag:
- PA2253
- Molecular weight:
- 34.8 kDa
Reactions
| L-asparagine + H(2)O = L-aspartate + NH(3). |
- General function:
- Involved in aspartate ammonia-lyase activity
- Specific function:
- L-aspartate = fumarate + NH(3)
- Gene Name:
- aspA
- Locus Tag:
- PA5429
- Molecular weight:
- 51.1 kDa
Reactions
| L-aspartate = fumarate + NH(3). |
- General function:
- Involved in electron carrier activity
- Specific function:
- Catalyzes the oxidation of L-aspartate to iminoaspartate
- Gene Name:
- nadB
- Locus Tag:
- PA0761
- Molecular weight:
- 60 kDa
Reactions
| L-aspartate + O(2) = iminosuccinate + H(2)O(2). |
- General function:
- Involved in nucleotide binding
- Specific function:
- ATP + L-aspartate + tRNA(Asp) = AMP + diphosphate + L-aspartyl-tRNA(Asp)
- Gene Name:
- aspS
- Locus Tag:
- PA0963
- Molecular weight:
- 66.2 kDa
Reactions
| ATP + L-aspartate + tRNA(Asp) = AMP + diphosphate + L-aspartyl-tRNA(Asp). |
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- gltJ
- Locus Tag:
- PA1341
- Molecular weight:
- 27.6 kDa
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- gltK
- Locus Tag:
- PA1340
- Molecular weight:
- 24.6 kDa
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for glutamate and aspartate. Probably responsible for energy coupling to the transport system
- Gene Name:
- gltL
- Locus Tag:
- PA1339
- Molecular weight:
- 26.9 kDa
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for glutamate and aspartate. Binds to both aspartate and glutamate
- Gene Name:
- gltI
- Locus Tag:
- PA1342
- Molecular weight:
- 33.1 kDa
Transporters
- General function:
- Involved in nucleotide binding
- Specific function:
- Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
- Gene Name:
- yecC
- Locus Tag:
- PA5152
- Molecular weight:
- 28.4 kDa
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- gltJ
- Locus Tag:
- PA1341
- Molecular weight:
- 27.6 kDa
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for aspartate/glutamate; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- gltK
- Locus Tag:
- PA1340
- Molecular weight:
- 24.6 kDa
- General function:
- Involved in sodium:dicarboxylate symporter activity
- Specific function:
- This carrier protein is part of the Na(+)-independent, binding-protein-independent glutamate-aspartate transport system
- Gene Name:
- gltP
- Locus Tag:
- PA5479
- Molecular weight:
- 47.6 kDa
- General function:
- Involved in symporter activity
- Specific function:
- Responsible for the aerobic transport of the dicarboxylates fumarate, L- and D-malate and to a lesser extent succinate, from the periplasm across the inner membrane
- Gene Name:
- dctA
- Locus Tag:
- PA1183
- Molecular weight:
- 46 kDa
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the binding-protein-dependent transport system for glutamate and aspartate. Probably responsible for energy coupling to the transport system
- Gene Name:
- gltL
- Locus Tag:
- PA1339
- Molecular weight:
- 26.9 kDa
- General function:
- Involved in transporter activity
- Specific function:
- Part of the binding-protein-dependent transport system for glutamate and aspartate. Binds to both aspartate and glutamate
- Gene Name:
- gltI
- Locus Tag:
- PA1342
- Molecular weight:
- 33.1 kDa