Record Information
Version2.0
Creation Date2012-05-31 09:57:49 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00123
Identification
Name:Glycine
Description:Glycine is a simple amino acid. The glycine cleavage enzyme system comprises four proteins: P-, T-, H- and L-proteins (EC 1.4.4.2, EC 2.1.2.10 and EC 1.8.1.4 for P-, T- and L-proteins). The glycine cleavage system catalyses the oxidative conversion of glycine into carbon dioxide and ammonia, with the remaining one-carbon unit transferred to folate as methylenetetrahydrofolate. It is the main catabolic pathway for glycine and it also contributes to one-carbon metabolism.
Structure
Thumb
Synonyms:
  • 2-Aminoacetate
  • 2-Aminoacetic acid
  • Aciport
  • Amino-Acetate
  • Amino-Acetic acid
  • Aminoacetate
  • Aminoacetic acid
  • Aminoethanoate
  • Aminoethanoic acid
  • G
  • Glicoamin
  • Gly
  • Glycocoll
  • Glycolixir
  • Glycosthene
  • Gyn-Hydralin
  • Padil
Chemical Formula:C2H5NO2
Weight:Average: 75.0666
Monoisotopic: 75.032028409
InChI Key:DHMQDGOQFOQNFH-UHFFFAOYSA-N
InChI:InChI=1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
CAS number:56-40-6
IUPAC Name:2-aminoacetic acid
Traditional IUPAC Name:glycine
SMILES:NCC(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:504 deg F
Experimental Properties:
PropertyValueSource
Water Solubility:249.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-3.21 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility552.0 mg/mLALOGPS
logP-3.3ALOGPS
logP-3.4ChemAxon
logS0.87ALOGPS
pKa (Strongest Acidic)2.31ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16 m3·mol-1ChemAxon
Polarizability6.65 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Cysteinylglycine + Water > L-Cysteine + Glycine
L-Threonine <> Acetaldehyde + Glycine
L-Allothreonine > Acetaldehyde + Glycine
Glycine + NAD + Tetrahydrofolic acid > Carbon dioxide + 5,10-Methylene-THF + NADH + Ammonium
Adenosine triphosphate + Glycine + tRNA(Gly) + tRNA(Gly) <> Adenosine monophosphate + Glycyl-tRNA(Gly) + Pyrophosphate + Glycyl-tRNA(Gly)
Water + L-Prolinylglycine > Glycine + L-Proline
Water + Oxygen + Sarcosine > Formaldehyde + Glycine + Hydrogen peroxide
L-Serine + Tetrahydrofolic acid <> Glycine + Water + 5,10-Methylene-THF
Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Glutathione + Hydrogen ion + Phosphate
Acetyl-CoA + Glycine <> L-2-Amino-3-oxobutanoic acid + Coenzyme A
Adenosine triphosphate + Glycine + 5-Phosphoribosylamine <> ADP + Glycineamideribotide + Hydrogen ion + Phosphate
Acetyl-CoA + Glycine <> Coenzyme A + L-2-Amino-3-oxobutanoic acid
Adenosine triphosphate + gamma-Glutamylcysteine + Glycine <> ADP + Phosphate + Glutathione
L-Threonine <> Glycine + Acetaldehyde
Cysteinylglycine + Water <> L-Cysteine + Glycine
5,10-Methylene-THF + Glycine + Water <> Tetrahydrofolic acid + L-Serine
Glycine + Tetrahydrofolic acid + NAD <> 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH + Hydrogen ion
Glycine + Lipoylprotein <> S-Aminomethyldihydrolipoylprotein + Carbon dioxide
Adenosine triphosphate + Glycine + tRNA(Gly) <> Adenosine monophosphate + Pyrophosphate + Glycyl-tRNA(Gly)
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine <> ADP + Phosphate + Glycineamideribotide
R-S-Cysteinylglycine + Water <> S-Substituted L-cysteine + Glycine
L-Allothreonine <> Glycine + Acetaldehyde
L-Serine + 5,6,7,8-Tetrahydromethanopterin <> 5,10-Methylenetetrahydromethanopterin + Glycine + Water
NAD + Glycine + Tetrahydrofolic acid > Hydrogen ion + 5,10-Methylene-THF + Ammonia + Carbon dioxide + NADH
Glycine + Acetyl-CoA <> Hydrogen ion + L-2-Amino-3-oxobutanoic acid + Coenzyme A
Glycine + gamma-Glutamylcysteine + Adenosine triphosphate > Hydrogen ion + Glutathione + Phosphate + ADP
L-Serine + Tetrahydrofolic acid <> 5,10-Methylene-THF + Glycine + Water
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine <> Hydrogen ion + ADP + Phosphate + Glycineamideribotide
L-Allothreonine <> Glycine + Acetaldehyde
L-<i>threo</i>-3-phenylserine benzaldehyde + Glycine
Cysteinylglycine + Water > L-Cysteine + Glycine
DL-allothreonine <> Acetaldehyde + Glycine
4-Hydroxy-L-threonine <> Glycolaldehyde + Glycine
gly-met + Water > Glycine + L-Methionine
ala-gly + Water > L-Alanine + Glycine
gly-asn + Water > Glycine + L-Asparagine
gly-gln + Water > Glycine + L-Glutamine
glycyl-L-glutamate + Water > Glycine + L-Glutamate
gly-asp + Water > Glycine + L-Aspartic acid
glycylproline + Water > Glycine + L-Proline
L-Threonine > Acetaldehyde + Glycine
Glycine + H-protein-lipoyllysine > H-protein-S-aminomethyldihydrolipoyllysine + Carbon dioxide
5,10-Methylene-THF + Glycine + Water > Tetrahydrofolic acid + L-Serine
Adenosine triphosphate + gamma-Glutamylcysteine + Glycine > ADP + Inorganic phosphate + Glutathione
Acetyl-CoA + Glycine > CoA + L-2-Amino-3-oxobutanoic acid
L-Threonine > Glycine + Acetaldehyde
L-Allothreonine > Glycine + Acetaldehyde
Adenosine triphosphate + 5-Phosphoribosylamine + Glycine > ADP + Inorganic phosphate + 5'-Phospho-ribosylglycinamide
Adenosine triphosphate + Glycine + tRNA(Gly) > Adenosine monophosphate + Pyrophosphate + glycyl-tRNA(Gly)
Adenosine triphosphate + Glycine + tRNA(Gly) > Adenosine monophosphate + Pyrophosphate + glycyl-tRNA(Gly)
Tetrahydrofolic acid + L-Serine + Tetrahydrofolic acid + L-Serine <> 5,10-Methylene-THF + Glycine + Water + 5,10-Methylene-THF
L-Alanine + Glyoxylic acid + L-Alanine <> Glycine + Pyruvic acid
Glycine + Adenosine triphosphate + Hydrogen ion + tRNA(gly) > Adenosine monophosphate + Pyrophosphate + Glycyl-tRNA(Gly)
gamma-Glutamylcysteine + Glycine + Adenosine triphosphate > Hydrogen ion + Phosphate + Adenosine diphosphate + Glutathione + ADP
5-Phosphoribosylamine + Glycine + Adenosine triphosphate + 5-Phosphoribosylamine > N1-(5-phospho-β-D-ribosyl)glycinamide + Phosphate + Adenosine diphosphate + Hydrogen ion + ADP
L-2-Amino-3-oxobutanoic acid + Coenzyme A > Acetyl-CoA + Glycine
More...

SMPDB Pathways:
GLYCINE BIOSYNTHESISPW000808 Pw000808Pw000808 greyscalePw000808 simple
Glutathione metabolismPW000833 Pw000833Pw000833 greyscalePw000833 simple
Nitrogen metabolismPW000755 Pw000755Pw000755 greyscalePw000755 simple
One Carbon Pool by Folate IPW001735 Pw001735Pw001735 greyscalePw001735 simple
One carbon pool by folatePW000773 Pw000773Pw000773 greyscalePw000773 simple
Thiamin diphosphate biosynthesisPW002028 Pw002028Pw002028 greyscalePw002028 simple
glutathione metabolism IIPW001927 Pw001927Pw001927 greyscalePw001927 simple
glutathione metabolism IIIPW002018 Pw002018Pw002018 greyscalePw002018 simple
inner membrane transportPW000786 Pw000786Pw000786 greyscalePw000786 simple
purine nucleotides de novo biosynthesisPW000910 Pw000910Pw000910 greyscalePw000910 simple
purine nucleotides de novo biosynthesis 1435709748PW000960 Pw000960Pw000960 greyscalePw000960 simple
purine nucleotides de novo biosynthesis 2PW002033 Pw002033Pw002033 greyscalePw002033 simple
tRNA Charging 2PW000803 Pw000803Pw000803 greyscalePw000803 simple
tRNA chargingPW000799 Pw000799Pw000799 greyscalePw000799 simple
threonine biosynthesisPW000817 Pw000817Pw000817 greyscalePw000817 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
318± 0 uMBW2511348 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoStationary Phase, glucose limitedBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h37 oCPMID: 17379776
235± 14 uMBL21 DE3Luria-Bertani (LB) mediaStationary phase cultures (overnight culture)Shake flask37 oCExperimentally Determined
Download Details
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00dj-2900000000-0ef96bcf06ce475afcddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-00dj-1900000000-1d289099ac79cfb8bb19View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-7910000000-6c972a683dfb75b69331View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0udi-0900000000-ef69e38ee6cebc2ece00View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2910000000-3215b9e40f20c7b306cdView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-001i-9000000000-f0a2cfbefb9fcd9b6c3eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-719b7f248956f13a312dView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-0900000000-99b4fc43740b21edc786View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-00di-1910000000-4cff4d14c73acff9442fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00dj-2900000000-0ef96bcf06ce475afcddView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00dj-1900000000-1d289099ac79cfb8bb19View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQsplash10-0002-4960000000-2c6fa028e985c6019854View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00di-7910000000-6c972a683dfb75b69331View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-00di-2910000000-3215b9e40f20c7b306cdView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0udi-0900000000-ef69e38ee6cebc2ece00View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-00ds-2900000000-ffffed9c78c16a884e4aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-004r-3900000000-f288b50b7b6890429811View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-1900000000-c76140c31c1f120e4b9dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00di-9300000000-b8bbfc1276d5adb1ba04View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-9000000000-725357e461c898a7451eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-9f3930e66b117ad91dcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-9000000000-b3336097dddbb5e22871View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-001i-9000000000-719b7f248956f13a312dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-9000000000-6001578fc511ba3fefefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9000000000-79b2a0a9d93de6a62358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-9290dbe208c4744f4431View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-9000000000-342ab462db0835abb3d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0ar1-9010000000-9daadc1d169a8530926dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-07y0-9220000000-8c7785f1f3aa8052679fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0ula-9110000000-43ada06fe1b56b4e9fccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-017i-9000000000-fbd78fbb48f082235f42View in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-004i-9000000000-c38d0fb28793438083a9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Positivesplash10-004i-9000000000-18a7ae48c7b0e15cdf18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-6001578fc511ba3fefefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-79b2a0a9d93de6a62358View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-9290dbe208c4744f4431View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-9000000000-605b44ac311a9af4bb7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-9000000000-342ab462db0835abb3d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0059-9000000000-c6b1ebc1dba89b6a6184View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-851aa6a0263541a8b249View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-d3b5624412082bb2cf60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-89b2c043a5afe3ebc6f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-b4046e208ee8adb87021View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-36521e440c602bd2ca5aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-222d6c3a1ba6afcd7ea9View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. Pubmed: 6321058
  • Bennett FI, Jackson AA: Glycine is not formed through the amino transferase reaction in human or rat placenta. Placenta. 1998 May;19(4):329-31. Pubmed: 9639330
  • Boneh A, Degani Y, Harari M: Prognostic clues and outcome of early treatment of nonketotic hyperglycinemia. Pediatr Neurol. 1996 Sep;15(2):137-41. Pubmed: 8888048
  • Byard RW, Harrison R, Wells R, Gilbert JD: Glycine toxicity and unexpected intra-operative death. J Forensic Sci. 2001 Sep;46(5):1244-6. Pubmed: 11569574
  • Christie GR, Ford D, Howard A, Clark MA, Hirst BH: Glycine supply to human enterocytes mediated by high-affinity basolateral GLYT1. Gastroenterology. 2001 Feb;120(2):439-48. Pubmed: 11159884
  • Collins JW, Macdermott S, Bradbrook RA, Keeley FX Jr, Timoney AG: Is using ethanol-glycine irrigating fluid monitoring and 'good surgical practice' enough to prevent harmful absorption during transurethral resection of the prostate? BJU Int. 2006 Jun;97(6):1247-51. Pubmed: 16686720
  • Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216
  • Dicke JM, Verges D, Kelley LK, Smith CH: Glycine uptake by microvillous and basal plasma membrane vesicles from term human placentae. Placenta. 1993 Jan-Feb;14(1):85-92. Pubmed: 8456092
  • Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
  • Gomeza J, Ohno K, Hulsmann S, Armsen W, Eulenburg V, Richter DW, Laube B, Betz H: Deletion of the mouse glycine transporter 2 results in a hyperekplexia phenotype and postnatal lethality. Neuron. 2003 Nov 13;40(4):797-806. Pubmed: 14622583
  • Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473
  • Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597. Pubmed: 17379776
  • Jones CM, Smith M, Henderson MJ: Reference data for cerebrospinal fluid and the utility of amino acid measurement for the diagnosis of inborn errors of metabolism. Ann Clin Biochem. 2006 Jan;43(Pt 1):63-6. Pubmed: 16390611
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • Khan SA, Cox IJ, Hamilton G, Thomas HC, Taylor-Robinson SD: In vivo and in vitro nuclear magnetic resonance spectroscopy as a tool for investigating hepatobiliary disease: a review of H and P MRS applications. Liver Int. 2005 Apr;25(2):273-81. Pubmed: 15780050
  • Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. Pubmed: 6696735
  • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
  • Prescot AP, de B Frederick B, Wang L, Brown J, Jensen JE, Kaufman MJ, Renshaw PF: In vivo detection of brain glycine with echo-time-averaged (1)H magnetic resonance spectroscopy at 4.0 T. Magn Reson Med. 2006 Mar;55(3):681-6. Pubmed: 16453318
  • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
  • Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Van Hove JL, Vande Kerckhove K, Hennermann JB, Mahieu V, Declercq P, Mertens S, De Becker M, Kishnani PS, Jaeken J: Benzoate treatment and the glycine index in nonketotic hyperglycinaemia. J Inherit Metab Dis. 2005;28(5):651-63. Pubmed: 16151895
  • Vijayendran, C., Barsch, A., Friehs, K., Niehaus, K., Becker, A., Flaschel, E. (2008). "Perceiving molecular evolution processes in Escherichia coli by comprehensive metabolite and gene expression profiling." Genome Biol 9:R72. Pubmed: 18402659
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Anslow, Winston K.; King, Harold. Synthesis of glycine. Journal of the Chemical Society (1929), 2163-6.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15428
HMDB IDHMDB00123
Pubchem Compound ID750
Kegg IDC00037
ChemSpider ID730
WikipediaGlycine
BioCyc IDGLY
EcoCyc IDGLY
Ligand ExpoGLY_LFZW

Enzymes

General function:
Involved in nucleotide binding
Specific function:
ATP + glycine + tRNA(Gly) = AMP + diphosphate + glycyl-tRNA(Gly)
Gene Name:
glyQ
Uniprot ID:
P00960
Molecular weight:
34774
Reactions
ATP + glycine + tRNA(Gly) = AMP + diphosphate + glycyl-tRNA(Gly).
General function:
Involved in arginine-tRNA ligase activity
Specific function:
ATP + glycine + tRNA(Gly) = AMP + diphosphate + glycyl-tRNA(Gly)
Gene Name:
glyS
Uniprot ID:
P00961
Molecular weight:
76812
Reactions
ATP + glycine + tRNA(Gly) = AMP + diphosphate + glycyl-tRNA(Gly).
General function:
Involved in ATP binding
Specific function:
ATP + gamma-L-glutamyl-L-cysteine + glycine = ADP + phosphate + glutathione
Gene Name:
gshB
Uniprot ID:
P04425
Molecular weight:
35561
Reactions
ATP + gamma-L-glutamyl-L-cysteine + glycine = ADP + phosphate + glutathione.
General function:
Involved in proteolysis
Specific function:
Aminopeptidase N is involved in the degradation of intracellular peptides generated by protein breakdown during normal growth as well as in response to nutrient starvation
Gene Name:
pepN
Uniprot ID:
P04825
Molecular weight:
98918
Reactions
Release of an N-terminal amino acid, Xaa-|-Yaa- from a peptide, amide or arylamide. Xaa is preferably Ala, but may be most amino acids including Pro (slow action). When a terminal hydrophobic residue is followed by a prolyl residue, the two may be released as an intact Xaa-Pro dipeptide.
General function:
Involved in catalytic activity
Specific function:
Interconversion of serine and glycine
Gene Name:
glyA
Uniprot ID:
P0A825
Molecular weight:
45316
Reactions
5,10-methylenetetrahydrofolate + glycine + H(2)O = tetrahydrofolate + L-serine.
General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the glycine cleavage system as well as of the alpha-ketoacid dehydrogenase complexes
Gene Name:
lpdA
Uniprot ID:
P0A9P0
Molecular weight:
50688
Reactions
Protein N(6)-(dihydrolipoyl)lysine + NAD(+) = protein N(6)-(lipoyl)lysine + NADH.
General function:
Involved in glycine C-acetyltransferase activity
Specific function:
Catalyzes the cleavage of 2-amino-3-ketobutyrate to glycine and acetyl-CoA
Gene Name:
kbl
Uniprot ID:
P0AB77
Molecular weight:
43117
Reactions
Acetyl-CoA + glycine = CoA + 2-amino-3-oxobutanoate.
General function:
Involved in hydrolase activity
Specific function:
Dipeptidase with broad substrate specificity. Requires dipeptide substrates with an unblocked N-terminus and the amino group in the alpha or beta position. Non-protein amino acids and proline are not accepted in the C-terminal position, whereas some dipeptide amides and formyl amino acids are hydrolyzed. Also shows cysteinylglycinase activity, which is sufficient for E.coli to utilize cysteinylglycine as a cysteine source
Gene Name:
pepD
Uniprot ID:
P15288
Molecular weight:
52915
Reactions
Hydrolysis of dipeptides, preferentially hydrophobic dipeptides including prolyl amino acids.
General function:
Involved in ATP binding
Specific function:
ATP + 5-phospho-D-ribosylamine + glycine = ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide
Gene Name:
purD
Uniprot ID:
P15640
Molecular weight:
45940
Reactions
ATP + 5-phospho-D-ribosylamine + glycine = ADP + phosphate + N(1)-(5-phospho-D-ribosyl)glycinamide.
General function:
Involved in aminomethyltransferase activity
Specific function:
The glycine cleavage system catalyzes the degradation of glycine
Gene Name:
gcvT
Uniprot ID:
P27248
Molecular weight:
40146
Reactions
[Protein]-S(8)-aminomethyldihydrolipoyllysine + tetrahydrofolate = [protein]-dihydrolipoyllysine + 5,10-methylenetetrahydrofolate + NH(3).
General function:
Involved in glycine dehydrogenase (decarboxylating) activity
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The P protein binds the alpha-amino group of glycine through its pyridoxal phosphate cofactor; CO(2) is released and the remaining methylamine moiety is then transferred to the lipoamide cofactor of the H protein
Gene Name:
gcvP
Uniprot ID:
P33195
Molecular weight:
104376
Reactions
Glycine + H-protein-lipoyllysine = H-protein-S-aminomethyldihydrolipoyllysine + CO(2).
General function:
Involved in aminopeptidase activity
Specific function:
Probably plays an important role in intracellular peptide degradation
Gene Name:
pepB
Uniprot ID:
P37095
Molecular weight:
46180
Reactions
Release of an N-terminal amino acid, Xaa, from a peptide or arylamide. Xaa is preferably Glu or Asp but may be other amino acids, including Leu, Met, His, Cys and Gln.
General function:
Involved in aminopeptidase activity
Specific function:
Presumably involved in the processing and regular turnover of intracellular proteins. Catalyzes the removal of unsubstituted N-terminal amino acids from various peptides. Required for plasmid ColE1 site-specific recombination but not in its aminopeptidase activity. Could act as a structural component of the putative nucleoprotein complex in which the Xer recombination reaction takes place
Gene Name:
pepA
Uniprot ID:
P68767
Molecular weight:
54879
Reactions
Release of an N-terminal amino acid, Xaa-|-Yaa-, in which Xaa is preferably Leu, but may be other amino acids including Pro although not Arg or Lys, and Yaa may be Pro. Amino acid amides and methyl esters are also readily hydrolyzed, but rates on arylamides are exceedingly low.
Release of an N-terminal amino acid, preferentially leucine, but not glutamic or aspartic acids.
General function:
Involved in lyase activity
Specific function:
Catalyzes the cleavage of L-allo-threonine and L- threonine to glycine and acetaldehyde. L-threo-phenylserine and L- erythro-phenylserine are also good substrates
Gene Name:
ltaE
Uniprot ID:
P75823
Molecular weight:
36494
Reactions
L-threonine = glycine + acetaldehyde.
L-allo-threonine = glycine + acetaldehyde.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative demethylation of N-methyl-L- tryptophan. Can also use other N-methyl amino acids, including sarcosine, which, however, is a poor substrate
Gene Name:
solA
Uniprot ID:
P40874
Molecular weight:
40902
Reactions
N-methyl-L-tryptophan + H(2)O + O(2) = L-tryptophan + formaldehyde + H(2)O(2).
General function:
Amino acid transport and metabolism
Specific function:
The glycine cleavage system catalyzes the degradation of glycine. The H protein shuttles the methylamine group of glycine from the P protein to the T protein
Gene Name:
gcvH
Uniprot ID:
P0A6T9
Molecular weight:
13811

Transporters

General function:
Involved in proteolysis
Specific function:
Aminopeptidase N is involved in the degradation of intracellular peptides generated by protein breakdown during normal growth as well as in response to nutrient starvation
Gene Name:
pepN
Uniprot ID:
P04825
Molecular weight:
98918
Reactions
Release of an N-terminal amino acid, Xaa-|-Yaa- from a peptide, amide or arylamide. Xaa is preferably Ala, but may be most amino acids including Pro (slow action). When a terminal hydrophobic residue is followed by a prolyl residue, the two may be released as an intact Xaa-Pro dipeptide.
General function:
Involved in sodium:amino acid symporter activity
Specific function:
Specific function unknown
Gene Name:
yaaJ
Uniprot ID:
P30143
Molecular weight:
51662
General function:
Involved in nucleotide binding
Specific function:
Probably part of a binding-protein-dependent transport system yecCS for an amino acid. Probably responsible for energy coupling to the transport system
Gene Name:
yecC
Uniprot ID:
P37774
Molecular weight:
27677
General function:
Involved in transporter activity
Specific function:
Probably part of the binding-protein-dependent transport system yecCS for an amino acid; probably responsible for the translocation of the substrate across the membrane
Gene Name:
yecS
Uniprot ID:
P0AFT2
Molecular weight:
24801
General function:
Involved in transport
Specific function:
Permease that is involved in the transport across the cytoplasmic membrane of D-alanine, D-serine and glycine
Gene Name:
cycA
Uniprot ID:
P0AAE0
Molecular weight:
51659
General function:
Involved in transporter activity
Specific function:
Probable transporter whose substrate is unknown. Is not involved in aerobic D-malate transport
Gene Name:
yeaV
Uniprot ID:
P0ABD1
Molecular weight:
52881
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368