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DL-asparagine

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Also known as Asn, Asparagine, Aspartamic acid, N, asparagine, 2-amino-3-carbamoylpropanoic acid, 2,4-diamino-4-oxobutanoic acid, Hasp

thumb|Asparagine ball and stick model spinning Asparagine (symbol Asn or N) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain carboxamide, classifying it as a polar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it. It is encoded by the codons AAU and AAC.

OverviewAI-generated

DL-asparagine is a chemical compound with the formula C₄H₈N₂O₃. Its IUPAC name is 4-amino-2-azaniumyl-4-oxobutanoate. The substance has a mass of 132.053 and a weight of 132.12. It possesses a charge of 0, an xlogp value of -2.8, and a topological polar surface area of 111. The molecule contains two hydrogen bond donors and three hydrogen bond acceptors.

The canonical SMILES notation for DL-asparagine is C(C(C(=O)O)N)C(=O)N, while its SMILES representation is C(C(C(=O)[O-])[NH3+])C(=O)N. The compound is associated with the Commons category "Asparagine". It has been referenced by 917 other encyclopedia articles and is the subject of 12 PubMed entries.

Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C4H8N2O3
Molecular weight: 132.12 g/mol
IUPAC name: 2,4-diamino-4-oxobutanoic acid
SMILES: C(C(C(=O)O)N)C(=O)N
InChIKey: DCXYFEDJOCDNAF-UHFFFAOYSA-N
XLogP: -3.4
Polar surface area: 106 Å²
H-bond donors: 3
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

12 papers

The optical resolution of DL-aspartic acid, DL-glutamic acid, DL-asparagine and DL-glutamine by preferential crystallization.Bulletin of the Chemical Society of Japan · 1965Harada KDOI: 10.1246/bcsj.38.1552
Copper(II) ion promoted hydrolysis of DL-asparagine and DL-isoasparagine.Acta pharmaceutica Suecica · 1969Strömberg L
Methods for syntheses of N-methyl-DL-aspartic acid derivatives.Amino acids · 2007Boros M, Kökösi J, Vámos J et al.DOI: 10.1007/s00726-006-0453-4
Salivary Metabolomics as a Diagnostic Tool: Distinct Metabolic Profiles Across Orofacial Pain Subtypes.International journal of molecular sciences · 2025Jasinska W, Birenzweig Y, Sharav Y et al.DOI: 10.3390/ijms26052260
Simultaneous measurement of amino acid enantiomers in the serum of late-life depression patients using convenient LC-MS/MS method with N(α)-(5-fluoro-2,4-dinitrophenyl)-l-leucinamide Derivatization.Journal of pharmaceutical and biomedical analysis · 2023Liu M, He J, Ruan C et al.DOI: 10.1016/j.jpba.2023.115387
[Synthesis of DL-asparagine suitable for the production of labelled N-15 and C-14 compounds].Biokhimiia (Moscow, Russia) · 1962LERMAN MI, MARDASHEV SR
Freezing effect on chirality amplification of L-asparagine by crystallization of the racemate in preferential condition.Cryo letters · 2011Vajda T, Hollósi MM
Studies on the role of protein synthesis and of sodium on the regulation of ornithine decarboxylase activity.Biochimica et biophysica acta · 1982Viceps-Madore D, Chen KY, Tsou HR et al.DOI: 10.1016/0304-4165(82)90184-2

Wikidata facts

Subclass of: carboxamides
Has part: carbon
Named after: Asparagus
Mass: 132.053

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Commons category: Asparagine
chemical formula: C₄H₈N₂O₃
found in taxon: Caenorhabditis elegans
described by source: Encyclopædia Britannica 11th edition
canonical SMILES: C(C(C(=O)O)N)C(=O)N

Sources (4)

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Encyclopedic overview

10 sections

Contents

History
Structural function in proteins
Sources
Dietary sources
Biosynthesis and catabolism
Acrylamide controversy
Function
See also
References
External links

thumb|Asparagine ball and stick model spinning Asparagine (symbol Asn or N) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −COO− form under biological conditions), and a side chain carboxamide, classifying it as a polar (at physiological pH), aliphatic amino acid. It is non-essential in humans, meaning the body can synthesize it. It is encoded by the codons AAU and AAC.

The one-letter symbol N for asparagine was assigned arbitrarily, with the proposed mnemonic asparagiNe;

Excerpted from Wikipedia’s “DL-asparagine” article, available under the CC BY-SA 4.0 licence.

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