L-Asparagine (ECMDB00168) (M2MDB000069)
| Record Information | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2012-05-31 10:22:45 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2015-09-13 12:56:06 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Name: | L-Asparagine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Asparagine (Asn) is one of the 20 most common natural amino acids on Earth. It has carboxamide as the side chain's functional group. It is considered a non-essential amino acid. The precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. The enzyme transfers the amino group from glutamate to oxaloacetate producing alpha-ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming beta-aspartyl-AMP. glutamine donates an ammonium group which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Since the asparagine side chain can make efficient hydrogen bond interactions with the peptide backbone, asparagines are often found near the beginning and end of alpha-helices, and in turn motifs in beta sheets. Its role can be thought as "capping" the hydrogen bond interactions which would otherwise need to be satisfied by the polypeptide backbone. Glutamines have an extra methylene group, have more conformational entropy and thus are less useful in this regard. Asparagine also provides key sites for N-linked glycosylation, modification of the protein chain with the addition of carbohydrate chains. (http://en.wikipedia.org/wiki/Asparagine) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure |  | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Formula: | C4H8N2O3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Weight: | Average: 132.1179 Monoisotopic: 132.053492132 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key: | DCXYFEDJOCDNAF-REOHCLBHSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI: | InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS number: | 70-47-3 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name: | (2S)-2-amino-3-carbamoylpropanoic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional IUPAC Name: | L-asparagine | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES: | N[C@@H](CC(N)=O)C(O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Carboxylic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Amino acids, peptides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Asparagine and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Charge: | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Melting point: | 234-235 °C | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Predicted Properties |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Reactions: | L-Asparagine + Water > L-Aspartic acid + Ammonium L-Aspartic acid + Adenosine triphosphate + L-Glutamine + Water > Adenosine monophosphate + L-Asparagine + L-Glutamate + Hydrogen ion + Pyrophosphate L-Asparagine + Adenosine triphosphate + tRNA(Asn) + tRNA(Asn) <> Adenosine monophosphate + L-Asparaginyl-tRNA(Asn) + Pyrophosphate + L-Asparaginyl-tRNA(Asn) L-Aspartic acid + Adenosine triphosphate + Ammonium > Adenosine monophosphate + L-Asparagine + Hydrogen ion + Pyrophosphate Adenosine triphosphate + L-Aspartic acid + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine L-Asparagine + Water <> L-Aspartic acid + Ammonia Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate Adenosine triphosphate + L-Asparagine + tRNA(Asn) <> Adenosine monophosphate + Pyrophosphate + L-Asparaginyl-tRNA(Asn) Ammonia + L-Aspartic acid + Adenosine triphosphate > L-Asparagine + Pyrophosphate + Adenosine monophosphate L-Asparagine + Water > Hydrogen ion + L-Aspartic acid + Ammonia gly-asn + Water > Glycine + L-Asparagine Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water > Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate L-Asparagine + Water > L-Aspartic acid + Ammonia Adenosine triphosphate + L-Asparagine + tRNA(Asn) > Adenosine monophosphate + Pyrophosphate + L-asparaginyl-tRNA(Asn) Adenosine triphosphate + L-Aspartic acid + L-Glutamine + Water + Ammonia <> Adenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamate 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-Asparagine + Adenosine triphosphate + Hydrogen ion + tRNA(Asn) + L-Asparagine > Pyrophosphate + Adenosine monophosphate + L-asparaginyl-tRNA(Asn) 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-Asparagine + Water + L-Asparagine > L-Aspartic acid + Ammonium + L-Aspartic acid L-Asparagine + Water <> L-Aspartic acid + Ammonia L-Asparagine + Water > Hydrogen ion + L-Aspartic acid + Ammonia | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMPDB Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| EcoCyc Pathways: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference: | Wang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links: |
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Enzymes
- General function:
- Involved in asparaginase activity
- Specific function:
- L-asparagine + H(2)O = L-aspartate + NH(3)
- Gene Name:
- ansB
- Uniprot ID:
- P00805
- Molecular weight:
- 36851
Reactions
| L-asparagine + H(2)O = L-aspartate + NH(3). |
- General function:
- Involved in nucleotide binding
- Specific function:
- ATP + L-aspartate + NH(3) = AMP + diphosphate + L-asparagine
- Gene Name:
- asnA
- Uniprot ID:
- P00963
- Molecular weight:
- 36650
Reactions
| ATP + L-aspartate + NH(3) = AMP + diphosphate + L-asparagine. |
- General function:
- Involved in nucleotide binding
- Specific function:
- ATP + L-asparagine + tRNA(Asn) = AMP + diphosphate + L-asparaginyl-tRNA(Asn)
- Gene Name:
- asnS
- Uniprot ID:
- P0A8M0
- Molecular weight:
- 52570
Reactions
| ATP + L-asparagine + tRNA(Asn) = AMP + diphosphate + L-asparaginyl-tRNA(Asn). |
- General function:
- Involved in asparaginase activity
- Specific function:
- L-asparagine + H(2)O = L-aspartate + NH(3)
- Gene Name:
- ansA
- Uniprot ID:
- P0A962
- Molecular weight:
- 37127
Reactions
| L-asparagine + H(2)O = L-aspartate + NH(3). |
- General function:
- Involved in asparagine synthase (glutamine-hydrolyzing) activity
- Specific function:
- ATP + L-aspartate + L-glutamine + H(2)O = AMP + diphosphate + L-asparagine + L-glutamate
- Gene Name:
- asnB
- Uniprot ID:
- P22106
- Molecular weight:
- 62659
Reactions
| ATP + L-aspartate + L-glutamine + H(2)O = AMP + diphosphate + L-asparagine + L-glutamate. |
- General function:
- Involved in hydrolase activity
- Specific function:
- May be involved in glutathione, and possibly other peptide, transport, although these results could also be due to polar effects of disruption
- Gene Name:
- iaaA
- Uniprot ID:
- P37595
- Molecular weight:
- 33394
Reactions
| Cleavage of a beta-linked Asp residue from the N-terminus of a polypeptide. |
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
- Uniprot ID:
- P37774
- Molecular weight:
- 27677
- General function:
- Involved in transporter activity
- Specific function:
- Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
- Gene Name:
- yecS
- Uniprot ID:
- P0AFT2
- Molecular weight:
- 24801
- General function:
- Involved in transport
- Specific function:
- Specific function unknown
- Gene Name:
- ansP
- Uniprot ID:
- P77610
- Molecular weight:
- 54233
- General function:
- Involved in transporter activity
- Specific function:
- Non-specific porin
- Gene Name:
- ompN
- Uniprot ID:
- P77747
- Molecular weight:
- 41220
- General function:
- Involved in transporter activity
- Specific function:
- Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
- Gene Name:
- phoE
- Uniprot ID:
- P02932
- Molecular weight:
- 38922
- General function:
- Involved in transporter activity
- Specific function:
- OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
- Gene Name:
- ompF
- Uniprot ID:
- P02931
- Molecular weight:
- 39333
- General function:
- Involved in transporter activity
- Specific function:
- Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
- Gene Name:
- ompC
- Uniprot ID:
- P06996
- Molecular weight:
- 40368