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Identification
YMDB IDYMDB00226
NameL-Asparagine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAsparagine (abbreviated as Asn or N) is an alpha-amino acid. The L-isomer is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. It is classified as a polar amino acid, because of the hydrophilic nature of its alkyl-amide or alkyl-carboxamide side chain. Asparagine can be considered the amide of aspartic acid 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 alpha-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 beta-aspartyl-AMP. Glutamine donates an ammonium group, which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Aspartate is a glucogenic amino acid. L-asparaginase 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. A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature. These products occur in baked goods such as French fries, potato chips, and roasted coffee.
Structure
Thumb
Synonyms
  • (-)-Asparagine
  • (S)-2,4-Diamino-4-oxobutanoate
  • (S)-2,4-Diamino-4-oxobutanoic acid
  • (S)-Asparagine
  • 2-Aminosuccinamate
  • 2-Aminosuccinamic acid
  • a-Aminosuccinamate
  • a-Aminosuccinamic acid
  • Agedoite
  • alpha Amminosuccinamate
  • alpha Amminosuccinamic acid
  • alpha-Aminosuccinamate
  • alpha-Aminosuccinamic acid
  • Altheine
  • Asn
  • Asparagine
  • Asparagine acid
  • Asparamide
  • Aspartamate
  • Aspartamic acid
  • Aspartic acid amide
  • Aspartic acid b-amide
  • Aspartic acid beta amide
  • B2,4-(S)-diamino-4-oxo-utanoate
  • B2,4-(S)-diamino-4-oxo-utanoic acid
  • L-2,4-Diamino-4-oxobutanoate
  • L-2,4-Diamino-4-oxobutanoic acid
  • l-Asparagine
  • L-Aspartamine
  • L-b-Asparagine
  • L-beta-Asparagine
  • (2S)-2,4-Diamino-4-oxobutanoic acid
  • (2S)-2-Amino-3-carbamoylpropanoic acid
  • (S)-2-Amino-3-carbamoylpropanoic acid
  • L-2-Aminosuccinamic acid
  • L-Asparagin
  • L-Aspartic acid beta-amide
  • N
  • (2S)-2,4-Diamino-4-oxobutanoate
  • (2S)-2-Amino-3-carbamoylpropanoate
  • (S)-2-Amino-3-carbamoylpropanoate
  • Α-aminosuccinamate
  • Α-aminosuccinamic acid
  • L-2-Aminosuccinamate
  • L-Aspartate b-amide
  • L-Aspartate beta-amide
  • L-Aspartate β-amide
  • L-Aspartic acid b-amide
  • L-Aspartic acid β-amide
  • Crystal VI
CAS number70-47-3
WeightAverage: 132.1179
Monoisotopic: 132.053492132
InChI KeyDCXYFEDJOCDNAF-REOHCLBHSA-N
InChIInChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
IUPAC Name(2S)-2-amino-3-carbamoylpropanoic acid
Traditional IUPAC NameL-asparagine
Chemical FormulaC4H8N2O3
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C(=O)N([H])[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAsparagine and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting point234-235 °C
Experimental Properties
PropertyValueReference
Water Solubility29.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.82 [CHMELIK,J ET AL. (1991)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility168 g/LALOGPS
logP-3.4ALOGPS
logP-4.3ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)2ChemAxon
pKa (Strongest Basic)8.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.35 m³·mol⁻¹ChemAxon
Polarizability11.68 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
  • mitochondrion
  • vacuole
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB000787
SMPDB Pathways
Asparagine metabolismPW002274 ThumbThumb?image type=greyscaleThumb?image type=simple
Nitrogen metabolismPW002504 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Cyanoamino acid metabolismec00460 Map00460
Nitrogen metabolismec00910 Map00910
SMPDB Reactions
L-Aspartic acid + water + Adenosine triphosphate + L-GlutamineL-Asparagine + hydron + Adenosine monophosphate + L-Glutamic acid + Pyrophosphate
L-Aspartic acid + Adenosine triphosphate + AmmoniumL-Asparagine + Adenosine monophosphate + Pyrophosphate + hydron
L-Asparagine + waterL-Aspartic acid + Ammonium
Adenosine triphosphate + L-Aspartic acid + AmmoniaAdenosine monophosphate + L-Asparagine + Pyrophosphate
Adenosine triphosphate + L-Aspartic acid + L-Glutamine + waterAdenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid
KEGG Reactions
L-Aspartic acid + Adenosine triphosphate + water + L-GlutamineAdenosine monophosphate + Pyrophosphate + L-Asparagine + L-Glutamic acid + hydron
Adenosine triphosphate + L-Asparagine + tRNA(Asn) → Adenosine monophosphate + Pyrophosphate + Asn-tRNA(Asn)
L-Asparagine + waterL-Aspartic acid + Ammonium
L-Asparagine + water L-Aspartic acid + Ammonium
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
427 ± 21 µM YEB media with 0.5 mM glucoseaerobicBaker's yeastExperimentally Determined
Not Available
820 ± 116 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Zhu, X., Garrett, J., Schreve, J., Michaeli, T. (1996). "GNP1, the high-affinity glutamine permease of S. cerevisiae." Curr Genet 30:107-114.8660458
Synthesis Reference:Wang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp.
External Links:
ResourceLink
CHEBI ID17196
HMDB IDHMDB00168
Pubchem Compound ID6267
Kegg IDC00152
ChemSpider ID6031
FOODB IDFDB000787
WikipediaAsparagine
BioCyc IDASN

Enzymes

General function:
Involved in asparagine synthase (glutamine-hydrolyzing) activity
Specific function:
ATP + L-aspartate + L-glutamine + H(2)O = AMP + diphosphate + L-asparagine + L-glutamate
Gene Name:
ASN1
Uniprot ID:
P49089
Molecular weight:
64469.60156
Reactions
ATP + L-aspartate + L-glutamine + H(2)O → AMP + diphosphate + L-asparagine + L-glutamate.
General function:
Involved in asparagine synthase (glutamine-hydrolyzing) activity
Specific function:
ATP + L-aspartate + L-glutamine + H(2)O = AMP + diphosphate + L-asparagine + L-glutamate
Gene Name:
ASN2
Uniprot ID:
P49090
Molecular weight:
64592.5
Reactions
ATP + L-aspartate + L-glutamine + H(2)O → AMP + diphosphate + L-asparagine + L-glutamate.
General function:
Involved in asparaginase activity
Specific function:
L-asparagine + H(2)O = L-aspartate + NH(3)
Gene Name:
ASP3-1
Uniprot ID:
P11163
Molecular weight:
38686.19922
Reactions
L-asparagine + H(2)O → L-aspartate + NH(3).
General function:
Involved in asparaginase activity
Specific function:
L-asparagine + H(2)O = L-aspartate + NH(3)
Gene Name:
ASP1
Uniprot ID:
P38986
Molecular weight:
41394.80078
Reactions
L-asparagine + H(2)O → L-aspartate + NH(3).
General function:
Involved in nucleotide binding
Specific function:
ATP + L-asparagine + tRNA(Asn) = AMP + diphosphate + L-asparaginyl-tRNA(Asn)
Gene Name:
SLM5
Uniprot ID:
P25345
Molecular weight:
56784.39844
Reactions
ATP + L-asparagine + tRNA(Asn) → AMP + diphosphate + L-asparaginyl-tRNA(Asn).
General function:
Involved in nucleotide binding
Specific function:
ATP + L-asparagine + tRNA(Asn) = AMP + diphosphate + L-asparaginyl-tRNA(Asn)
Gene Name:
DED81
Uniprot ID:
P38707
Molecular weight:
62206.30078
Reactions
ATP + L-asparagine + tRNA(Asn) → AMP + diphosphate + L-asparaginyl-tRNA(Asn).

Transporters

General function:
Amino acid transport and metabolism
Specific function:
Involved in amino acid efflux from the vacuole to the cytoplasm. Capable of transporting large neutral amino acids including tyrosine, glutamine, asparagine, isoleucine and leucine
Gene Name:
AVT3
Uniprot ID:
P36062
Molecular weight:
75458.70313
General function:
Amino acid transport and metabolism
Specific function:
Required for the vacuolar uptake of large neutral amino acids including tyrosine, glutamine, asparagine, isoleucine and leucine. Requires ATP for function
Gene Name:
AVT1
Uniprot ID:
P47082
Molecular weight:
65345.30078
General function:
Involved in transport
Specific function:
Permease for various amino acids as well as for GABA. Can also transport L-cysteine and beta-alanine
Gene Name:
GAP1
Uniprot ID:
P19145
Molecular weight:
65654.89844
General function:
Involved in transport
Specific function:
High affinity transport of glutamine. Also transport Leu, Ser, Thr, Cys, Met and Asn
Gene Name:
GNP1
Uniprot ID:
P48813
Molecular weight:
73597.39844
General function:
Amino acid transport and metabolism
Specific function:
Involved in amino acid efflux from the vacuole to the cytoplasm. Capable of transporting large neutral amino acids including tyrosine, glutamine, asparagine, isoleucine and leucine
Gene Name:
AVT4
Uniprot ID:
P50944
Molecular weight:
80025.0
General function:
Involved in transport
Specific function:
Can transport glutamate, aspartate, glutamine, asparagine, serine, alanine and glycine
Gene Name:
DIP5
Uniprot ID:
P53388
Molecular weight:
68096.70313
General function:
Involved in transport
Specific function:
Broad substrate range permease which transports asparagine and glutamine with intermediate specificity. Also transports Ala, Cys, Gly, Ile, Leu, Met, Phe, Ser, Thr, Tyr and Val. Important for the utilization of amino acids as a nitrogen source
Gene Name:
AGP1
Uniprot ID:
P25376
Molecular weight:
69670.70313