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Asparagine

For other uses of "Asn", see ASN (disambiguation).
Not to be confused with Aspartic acid.
l-Asparagine
Skeletal formula of L-asparagine
Skeletal formula of L-asparagine
Ball-and-stick model of the L-asparagine molecule as a zwitterion
Skeletal formula of L-asparagine under physiological conditions
Names
IUPAC name
Asparagine
Other names
2-Amino-3-carbamoylpropanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.019.565 Edit this at Wikidata
EC Number
  • 200-735-9
KEGG
UNII
  • InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1 checkY
    Key: DCXYFEDJOCDNAF-REOHCLBHSA-N checkY
  • InChI=1/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
    Key: DCXYFEDJOCDNAF-REOHCLBHBD
  • O=C(N)C[C@H](N)C(=O)O
  • Zwitterion: O=C(N)C[C@H]([NH3+])C(=O)[O-]
Properties
C4H8N2O3
Molar mass 132.119 g·mol−1
Appearance white crystals
Density 1.543 g/cm3
Melting point 234 °C (453 °F; 507 K)
Boiling point 438 °C (820 °F; 711 K)
2.94 g/100 mL
Solubility soluble in acids, bases, negligible in methanol, ethanol, ether, benzene
log P −3.82
Acidity (pKa)
  • 2.1 (carboxyl; 20 °C, H2O)
  • 8.80 (amino; 20 °C, H2O)[1]
-69.5·10−6 cm3/mol
Structure
orthorhombic
Thermochemistry
−789.4 kJ/mol
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
0
0
Flash point 219 °C (426 °F; 492 K)
Safety data sheet (SDS) Sigma-Alrich
Supplementary data page
Asparagine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Asparagine (symbol Asn or N[2]) 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+
3 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,[3] with the proposed mnemonic asparagiNe;[4]

  1. ^ Haynes WM, ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
  2. ^ "Nomenclature and Symbolism for Amino Acids and Peptides". IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived from the original on 9 October 2008. Retrieved 5 March 2018.
  3. ^ "IUPAC-IUB Commission on Biochemical Nomenclature A One-Letter Notation for Amino Acid Sequences". Journal of Biological Chemistry. 243 (13): 3557–3559. 10 July 1968. doi:10.1016/S0021-9258(19)34176-6. Archived from the original on 20 February 2024. Retrieved 21 February 2024.
  4. ^ Adoga, Godwin I; Nicholson, Bh (January 1988). "Letters to the editor". Biochemical Education. 16 (1): 49. doi:10.1016/0307-4412(88)90026-X. Archived from the original on 2024-02-20. Retrieved 2024-02-21.

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أسبرجين Arabic آسپاراژین AZB Аспарагин Bulgarian অ্যাস্পারাজিন Bengali/Bangla Asparagin BS Asparagina Catalan Asparagin Czech Asparagin Danish Asparagin German Ασπαραγίνη Greek

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