L-Glutamine

• Formula: C₅H₁₀N₂O₃
• Molecular weight: 146.1445
• IUPAC Standard InChI: InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1 Copy

  
• IUPAC Standard InChIKey: ZDXPYRJPNDTMRX-GSVOUGTGSA-N Copy
• CAS Registry Number: 56-85-9
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Levoglutamide; γ-Glutamine; Cebrogen; Glumin; Glutamic acid amide; Glutamic acid 5-amide; Glutamine; L-Glutamic acid γ-amide; L-Glutamid; L-Glutamide; L-2-Aminoglutaramidic acid; Miglu-P; Pentanoic acid, 2,5-diamino-5-oxo-, (S)-; Stimulina; 2-Aminoglutaramic acid; Levoglutamid; L-(+)-glutamine; (S)-2,5-Diamino-5-oxopentanoic acid; Glumin (amino acid); NSC 27421; Saforis; Glutamine, L-
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
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Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₅H₉N₂O₃^- +  =

By formula: C₅H₉N₂O₃^- + H⁺ = C₅H₁₀N₂O₃

 +  = ( • )

By formula: Na⁺ + C₅H₁₀N₂O₃ = (Na⁺ • C₅H₁₀N₂O₃)

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess

De-protonation reactions

C₅H₉N₂O₃^- +  =

By formula: C₅H₉N₂O₃^- + H⁺ = C₅H₁₀N₂O₃

Ion clustering data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

By formula: Na⁺ + C₅H₁₀N₂O₃ = (Na⁺ • C₅H₁₀N₂O₃)

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Tsuzuki and Hunt, 1957
Tsuzuki, T.; Hunt, H., Heats of combustion. VI. The heats of combustion of some amino acids, J. Phys. Chem., 1957, 61, 1668. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Hutchens, Cole, et al., 1963
Hutchens, J.O.; Cole, A.G.; Robie, R.A.; Stout, J.W., Heat capacities from 11 to 305 K, entropies, and free energies of formation of L-aspartic acid, L-glutamic acid, and L-glutamine, J. Biol. Chem., 1963, 238, 2407-2412. [all data]

Jones, Bernier, et al., 2007
Jones, C.M.; Bernier, M.; Carson, E.; Colyer, K.E.; Metz, R.; Pawlow, A.; Wischow, E.D.; Webb, I.; Andriole, E.J.; Poutsma, J.C., Gas-phase Acities of the 20 Protein Amino Acids, Int. J. Mass Spectrom., 2007, 267, 1-3, 54-62, https://doi.org/10.1016/j.ijms.2007.02.018 . [all data]

O'Hair, Bowie, et al., 1992
O'Hair, R.J.; Bowie, J.H.; Gronert, S., Gas Phase Acidity of the alpha-Amino Acids, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 23, https://doi.org/10.1016/0168-1176(92)80083-D . [all data]

Kish, Ohanessian, et al., 2003
Kish, M.M.; Ohanessian, G.; Wesdemiotis, C., The Na+ affinities of a-amino acids: side-chain substituent effects, Int. J. Mass Spectrom., 2003, 227, 3, 509, https://doi.org/10.1016/S1387-3806(03)00082-4 . [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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