MetaCyc Compound: D-asparagine

Superclasses: an amino acid or its derivative an amino acid a D-amino acid
an amino acid or its derivative an amino acid a polar amino acid an uncharged polar amino acid

Chemical Formula: C4H8N2O3

Molecular Weight: 132.12 Daltons

Monoisotopic Molecular Weight: 132.0534921335 Daltons

D-asparagine compound structure

SMILES: C(CC(C(=O)[O-])[N+])(N)=O

InChI: InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m1/s1


Unification Links: ChEBI:74337 , HMDB:HMDB33780 , KEGG:C01905 , MetaboLights:MTBLC74337 , PubChem:6991971

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -41.14103 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

Not in pathways:
a D-amino acid[in] + an electron-transfer quinone[membrane] + H2O[in] → a 2-oxo carboxylate[in] + ammonium[in] + an electron-transfer quinol[membrane]
a D-amino acid + oxygen + H2O → ammonium + hydrogen peroxide + a 2-oxo carboxylate

Reactions known to produce the compound:

Not in pathways:
a peptide with an N-terminal D-amino acid + H2O → a peptide + a D-amino acid + H+
a D-aminoacyl-[tRNA] + H2O → a D-amino acid + an uncharged tRNA + 2 H+

In Reactions of unknown directionality:

Not in pathways:
acetyl-CoA + a D-amino acid = an N-acetyl-D-amino acid + coenzyme A + H+
an N-carbamoyl D-amino acid + H+ + H2O = a D-amino acid + ammonium + CO2
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an L-amino acid = a D-amino acid

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

In Transport reactions:
a polar amino acid[extracellular space] + ATP + H2O ↔ a polar amino acid[cytosol] + ADP + phosphate

In Redox half-reactions:
a 2-oxo carboxylate[in] + ammonium[in] + 2 H+[in] + 2 e-[membrane]a D-amino acid[in] + H2O[in]

Enzymes inhibited by D-asparagine, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: L-asparaginase [Pritsa01]

Inhibitor (Mechanism unknown) of: L-asparaginase [Raha90]

This compound has been characterized as an alternative substrate of the following enzymes: D-alanine--D-serine ligase , D-amino-acid:quinone oxidoreductase (deaminating) , L-asparaginase


Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Pritsa01: Pritsa AA, Kyriakidis DA (2001). "L-asparaginase of Thermus thermophilus: purification, properties and identification of essential amino acids for its catalytic activity." Mol Cell Biochem 216(1-2);93-101. PMID: 11216870

Raha90: Raha SK, Roy SK, Dey SK, Chakrabarty SL (1990). "Purification and properties of an L-asparaginase from Cylindrocarpon obtusisporum MB-10." Biochem Int 21(6);987-1000. PMID: 2080924

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Fri Apr 17, 2015, BIOCYC14B.