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Encyclopedia > Asparagine
Chemical structure of Asparagine 3D structure of Asparagine

Asparagine Image File history File links Download high resolution version (1267x1496, 23 KB) Licensing File links The following pages link to this file: Amino acid Asparagine User:Benjah-bmm27/Gallery ... Image File history File links Download high resolution version (517x733, 21 KB) Licensing File links The following pages link to this file: Asparagine User:Benjah-bmm27/Gallery ...

Systematic (IUPAC) name
(2S)-2-amino-3-carbamoyl-propanoic acid
Identifiers
CAS number 70-47-3
PubChem         236
Chemical data
Formula C4H8N2O3 
Mol. weight 132.118
Complete data
For other articles using the abbreviation or acronym asn see ASN.

Asparagine 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. IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... PubChem is a database of chemical molecules. ... This article does not cite its references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... Physical properties Hazard properties Flash point - N/A R/S statement R: N/A S: N/A RTECS number: N/A Chemical properties Pharmacological properties OrganicBox_complete References a  CID 6267 from PubChem (L-asparagine) This article is maintained by WP:Chemicals (Talk)  WP:Drugs (Talk)  WP:Molecular and Cellular Biology... ASN may mean Advanced Shipping Notice Atlantic Satellite Network Asparagine The National Rail code for Addlestone railway station, United Kingdom. ... Phenylalanine is one of the standard amino acids. ... Adjectives: Terrestrial, Terran, Telluric, Tellurian, Earthly Atmosphere Surface pressure: 101. ... Carboxamides are drugs that can be used as anticonvulsants. ... The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ... In organic chemistry, functional groups are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... An essential amino acid or indispensable amino acid, is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet. ...


Its three-letter abbreviation is Asn, and its one-letter abbreviation is N. A three-letter designation for either asparagine or aspartic acid is Asx (one-letter abbreviation: B). Aspartic acid (Asp), 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. ...


A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature, i.e. baking. These occur primarily in baked goods such as french fries, potato chips, and roasted coffee. A reducing sugar is a type of sugar with a ketone or aldehyde group. ... Carbonyl group In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom. ... This article or section does not adequately cite its references or sources. ...


Asparagine was first isolated in 1806 from asparagus juice, in which it is abundant--hence its name--becoming the first amino acid to be isolated. The smell observed in the urine of individuals after their consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. (However, some scientists disagree and implicate other substances in the smell, especially methanethiol). Oddly, some people are not able to detect the odour of the compound. 1806 was a common year starting on Wednesday (see link for calendar). ... Binomial name Asparagus officinalis L. Asparagus is a type of vegetable obtained from one species within the genus Asparagus, specifically the young shoots of Asparagus officinalis. ... Binomial name Asparagus officinalis L. Asparagus is a type of vegetable obtained from one species within the genus Asparagus, specifically the young shoots of Asparagus officinalis. ... Methanethiol (also known as methyl mercaptan) is a colorless gas with a smell like rotten cabbage. ...

Contents

Structural function in proteins

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. Glutamine is one of the 20 amino acids encoded by the standard genetic code. ...


Asparagine also provides key sites for N-linked glycosylation, modification of the protein chain with the addition of carbohydrate chains. Glycosylation is the process or result of addition of saccharides to proteins and lipids. ...


Biosynthesis

Asparagine is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. 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 α-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 β-aspartyl-AMP. Glutamine donates an ammonium group which reacts with β-aspartyl-AMP to form asparagine and free AMP.
An essential amino acid or indispensable amino acid, is an amino acid that cannot be synthesized de novo by the organism (usually referring to humans), and therefore must be supplied in the diet. ... Aspartic acid, 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. ... In biochemistry, a transaminase or an aminotransferase is an enzyme that catalyzes a type of reaction between an amino acid and an α-keto acid. ... Glutamate is the anion of glutamic acid. ... Ketoglutaric acid is refers to either of two crystalline ketone derivatives of glutaric acid which differ only by the position of the ketone functional group. ... Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. ... In chemistry, the anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. ... Glutamine is one of the 20 amino acids encoded by the standard genetic code. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Glutamine is one of the 20 amino acids encoded by the standard genetic code. ...

The biosynthesis of asparagine from oxaloacetate
The biosynthesis of asparagine from oxaloacetate

Image File history File links Asn_biosynthesis. ...

Degradation

Aspartate is a glucogenic amino acid. L-asparginase hydrolyzes the amide group to form aspartate and ammonium. A transaminase converts the aspartate to oxaloacetate which can then be metabolized in the citric acid cycle or gluconeogenesis. Overview of the citric acid cycle The citric acid cycle (also known as the tricarboxylic acid cycle, the TCA cycle, or the Krebs cycle, after Hans Adolf Krebs who identified the cycle) is a series of chemical reactions of central importance in all living cells that use oxygen as part... Pyruvic acid Oxaloacetic acid Phosphoenolpyruvate Fructose 1,6-bisphosphate Fructose 6-phosphate Glucose-6-phosphate Glucose Gluconeogenesis is the generation of glucose from non-sugar carbon substrates like pyruvate, lactate, glycerol, and amino acids (primarily alanine and glutamine). ...


Function

The nervous system needs asparagine to maintain the equilibrium, as well as in amino acid transformation. It also plays an important role in the synthesis of ammonia.


Sources

Dairy products, potatoes, beef, poultry, meat, and eggs.


External links

  • Links to external chemical sources


v  d  e
Major Families of Biochemicals
Peptides | Amino acids | Nucleic acids | Carbohydrates | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides
Analogues of nucleic acids: The 20 Common Amino Acids Analogues of nucleic acids:
Alanine (dp) | Arginine (dp) | Asparagine (dp) | Aspartic acid (dp) | Cysteine (dp) | Glutamic acid (dp) | Glutamine (dp) | Glycine (dp) | Histidine (dp) | Isoleucine (dp) | Leucine (dp) | Lysine (dp) | Methionine (dp) | Phenylalanine (dp) | Proline (dp) | Serine (dp) | Threonine (dp) | Tryptophan (dp) | Tyrosine (dp) | Valine (dp)

  Results from FactBites:
 
asparagine. The Columbia Encyclopedia, Sixth Edition. 2001-05 (200 words)
Like glutamine, asparagine is important in the metabolism of toxic ammonia in the body.
Asparagine is not essential to the human diet, since it can be synthesized from aspartic acid.
The first amino acid to be isolated from its natural source, asparagine was purified from asparagus juice in 1806; proof of the occurrence of this amino acid in proteins was finally obtained in 1932.
BioMed Central | Full text | A glutamine-amidotransferase-like protein modulates FixT anti-kinase activity in ... (4207 words)
Complementation test and DNA analysis revealed that inactivation of an asparagine synthetase-like gene was responsible for the phenotype of the mutant.
The reactions catalyzed by asparagine synthetases involve two different family of proteins depending on whether glutamine or ammonia is used as a nitrogen source.
Boehlein SK, Richards NG, Walworth ES, Schuster SM: Arginine 30 and asparagine 74 have functional roles in the glutamine dependent activities of Escherichia coli asparagine synthetase B. J Biol Chem 1994, 269:26789-95.
  More results at FactBites »


 
 

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