Record Information
Version2.0
Creation Date2012-07-30 14:55:19 -0600
Update Date2015-06-03 17:21:10 -0600
Secondary Accession Numbers
  • ECMDB21328
Identification
Name:Dehydroglycine
Description:Dehydroglycine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).Dehydroglycine is catalyzed by ThiH. ThiH is a tyrosine lyase that cleaves the C alpha-C beta bond of tyrosine, generating p-cresol as a by-product, to form dehydroglycine. (PMID 19923213)
Structure
Thumb
Synonyms:
  • 2-Iminoacetate
  • 2-Iminoacetic acid
  • Dehydroglycine
  • Iminoacetate
  • Iminoacetic acid
Chemical Formula:C2H2NO2
Weight:Average: 72.0428
Monoisotopic: 72.008553313
InChI Key:TVMUHOAONWHJBV-UHFFFAOYSA-M
InChI:InChI=1S/C2H3NO2/c3-1-2(4)5/h1,3H,(H,4,5)/p-1
CAS number:Not Available
IUPAC Name:2-iminoacetate
Traditional IUPAC Name:2-iminoacetate
SMILES:[O-]C(=O)C=N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Primary aldimine
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Aldimine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility9.41 mg/mLALOGPS
logP-0.94ALOGPS
logP-0.77ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)3.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.98 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.81 m3·mol-1ChemAxon
Polarizability5.49 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Thiazole Biosynthesis IPW002041 Pw002041Pw002041 greyscalePw002041 simple
KEGG Pathways:Not Available
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-7f7accee9d40e6bcea83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-0266621f8a393599804cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9000000000-1ab9d2576000afcc6a2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-a0b230949457ea313c0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-7c54e28c865a42d485a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-152493d50467ffb1c8bfView in MoNA
References
References:
  • Challand, M. R., Martins, F. T., Roach, P. L. (2010). "Catalytic activity of the anaerobic tyrosine lyase required for thiamine biosynthesis in Escherichia coli." J Biol Chem 285:5240-5248. Pubmed: 19923213
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID53664
HMDB IDNot Available
Pubchem Compound ID23347814
Kegg IDNot Available
ChemSpider ID15272272
Wikipedia IDNot Available
BioCyc IDCPD-12279
EcoCyc IDCPD-12279

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the removal of elemental sulfur and selenium atoms from cysteine and selenocysteine to produce alanine. Functions as a sulfur delivery protein for NAD, biotin and Fe-S cluster synthesis. Transfers sulfur on 'Cys-456' of thiI in a transpersulfidation reaction. Transfers sulfur on 'Cys-19' of tusA in a transpersulfidation reaction. Functions also as a selenium delivery protein in the pathway for the biosynthesis of selenophosphate
Gene Name:
iscS
Uniprot ID:
P0A6B7
Molecular weight:
45089
Reactions
L-cysteine + acceptor = L-alanine + S-sulfanyl-acceptor.
General function:
Involved in nucleotide binding
Specific function:
Catalyzes the adenylation by ATP of the carboxyl group of the C-terminal glycine of sulfur carrier protein ThiS
Gene Name:
thiF
Uniprot ID:
P30138
Molecular weight:
26970
Reactions
ATP + [ThiS] = diphosphate + adenylyl-[ThiS].
General function:
Involved in RNA binding
Specific function:
Catalyzes the ATP-dependent transfer of a sulfur to tRNA to produce 4-thiouridine in position 8 of tRNAs, which functions as a near-UV photosensor. Also catalyzes the transfer of sulfur to the sulfur carrier protein ThiS, forming ThiS-thiocarboxylate. This is a step in the synthesis of thiazole, in the thiamine biosynthesis pathway. The sulfur is donated as persulfide by iscS
Gene Name:
thiI
Uniprot ID:
P77718
Molecular weight:
54973
Reactions
L-cysteine + 'activated' tRNA = L-serine + tRNA containing a thionucleotide.
[IscS]-SSH + [ThiS]-COAMP = [IscS]-SH + [ThiS]-COSH + AMP.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the rearrangement of 1-deoxy-D-xylulose 5- phosphate (DXP) to produce the thiazole phosphate moiety of thiamine. Sulfur is provided by the thiocarboxylate moiety of the carrier protein ThiS. In vitro, sulfur can be provided by H(2)S
Gene Name:
thiG
Uniprot ID:
P30139
Molecular weight:
26896
Reactions
1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS] = 2-((2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + [sulfur-carrier protein ThiS] + 2 H(2)O.
General function:
Coenzyme transport and metabolism
Specific function:
Is the sulfur donor in the synthesis of the thiazole phosphate moiety of thiamine phosphate
Gene Name:
thiS
Uniprot ID:
O32583
Molecular weight:
7311
General function:
Involved in catalytic activity
Specific function:
Catalyzes the radical-mediated cleavage of tyrosine to dehydroglycine and p-cresol
Gene Name:
thiH
Uniprot ID:
P30140
Molecular weight:
43320
Reactions
L-tyrosine + S-adenosyl-L-methionine + reduced acceptor = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H(+).