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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-23 04:24:30 UTC
Update Date2023-02-21 17:30:59 UTC
HMDB IDHMDB0062557
Secondary Accession Numbers
  • HMDB62557
Metabolite Identification
Common NameN-Acetylthreonine
DescriptionN-Acetyl-L-threonine (or N-Acetylthreonine, belongs to the class of organic compounds known as N-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-Acetylthreonine can also be classified as an alpha amino acid or a derivatized alpha amino acid. Technically, N-Acetylthreonine is a biologically available N-terminal capped form of the proteinogenic alpha amino acid L-threonine. N-acetyl amino acids can be produced either via direct synthesis of specific N-acetyltransferases or via the proteolytic degradation of N-acetylated proteins by specific hydrolases. N-terminal acetylation of proteins is a widespread and highly conserved process in eukaryotes that is involved in protection and stability of proteins (PMID: 16465618 ). About 85% of all human proteins and 68% of all yeast proteins are acetylated at their N-terminus (PMID: 21750686 ). Several proteins from prokaryotes and archaea are also modified by N-terminal acetylation. The majority of eukaryotic N-terminal-acetylation reactions occur through N-acetyltransferase enzymes or NAT’s (PMID: 30054468 ). These enzymes consist of three main oligomeric complexes NatA, NatB, and NatC, which are composed of at least a unique catalytic subunit and one unique ribosomal anchor. The substrate specificities of different NAT enzymes are mainly determined by the identities of the first two N-terminal residues of the target protein. The human NatA complex co-translationally acetylates N-termini that bear a small amino acid (A, S, T, C, and occasionally V and G) (PMID: 30054468 ). NatA also exists in a monomeric state and can post-translationally acetylate acidic N-termini residues (D-, E-). NatB and NatC acetylate N-terminal methionine with further specificity determined by the identity of the second amino acid. N-acetylated amino acids, such as N-acetylthreonine can be released by an N-acylpeptide hydrolase from peptides generated by proteolytic degradation (PMID: 16465618 ). In addition to the NAT enzymes and protein-based acetylation, N-acetylation of free threonine can also occur. Excessive amounts N-acetyl amino acids including N-acetylthreonine (as well as N-acetylglycine, N-acetylserine, N-acetylmethionine, N-acetylglutamate, N-acetylalanine, N-acetylleucine and smaller amounts of N-acetylglutamine, N-acetylisoleucine, and N-acetylvaline) can be detected in the urine with individuals with acylase I deficiency, a genetic disorder (PMID: 16465618 ). Aminoacylase I is a soluble homodimeric zinc binding enzyme that catalyzes the formation of free aliphatic amino acids from N-acetylated precursors. In humans, Aminoacylase I is encoded by the aminoacylase 1 gene (ACY1) on chromosome 3p21 that consists of 15 exons (OMIM 609924 ). Individuals with aminoacylase I deficiency will experience convulsions, hearing loss and difficulty feeding (PMID: 16465618 ). ACY1 can also catalyze the reverse reaction, the synthesis of acetylated amino acids. Many N-acetylamino acids, including N-acetylthreonine are classified as uremic toxins if present in high abundance in the serum or plasma (PMID: 26317986 ; PMID: 20613759 ). Uremic toxins are a diverse group of endogenously produced molecules that, if not properly cleared or eliminated by the kidneys, can cause kidney damage, cardiovascular disease and neurological deficits (PMID: 18287557 ). N-Acetylthreonine has been identified in the human placenta (PMID: 32033212 ).
Structure
Data?1677000659
Synonyms
ValueSource
Ammonium N-acetyl-L-threoninateHMDB
Methylammonium N-acetyl-L-threoninateHMDB
N-Acetyl-L-threonineHMDB
N-AcetylthreonineMeSH
Chemical FormulaC6H11NO4
Average Molecular Weight161.1558
Monoisotopic Molecular Weight161.068807845
IUPAC Name(2S,3R)-2-acetamido-3-hydroxybutanoic acid
Traditional Name(2S,3R)-2-acetamido-3-hydroxybutanoic acid
CAS Registry Number17093-74-2
SMILES
C[C@@H](O)[C@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c1-3(8)5(6(10)11)7-4(2)9/h3,5,8H,1-2H3,(H,7,9)(H,10,11)/t3-,5+/m1/s1
InChI KeyPEDXUVCGOLSNLQ-WUJLRWPWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Hydroxy acid
  • Fatty acid
  • Acetamide
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility14.6 g/lALOGPS
LogP-0.60ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.92ALOGPS
logP-1.4ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.63 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.9 m³·mol⁻¹ChemAxon
Polarizability15.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.80231661259
DarkChem[M-H]-135.44731661259
DeepCCS[M+H]+134.00130932474
DeepCCS[M-H]-131.60530932474
DeepCCS[M-2H]-166.71430932474
DeepCCS[M+Na]+141.17330932474
AllCCS[M+H]+137.432859911
AllCCS[M+H-H2O]+133.532859911
AllCCS[M+NH4]+141.032859911
AllCCS[M+Na]+142.032859911
AllCCS[M-H]-130.432859911
AllCCS[M+Na-2H]-132.332859911
AllCCS[M+HCOO]-134.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-AcetylthreonineC[C@@H](O)[C@H](NC(C)=O)C(O)=O2589.5Standard polar33892256
N-AcetylthreonineC[C@@H](O)[C@H](NC(C)=O)C(O)=O1442.2Standard non polar33892256
N-AcetylthreonineC[C@@H](O)[C@H](NC(C)=O)C(O)=O1611.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetylthreonine,1TMS,isomer #1CC(=O)N[C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C1404.3Semi standard non polar33892256
N-Acetylthreonine,1TMS,isomer #2CC(=O)N[C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O1404.1Semi standard non polar33892256
N-Acetylthreonine,1TMS,isomer #3CC(=O)N([C@H](C(=O)O)[C@@H](C)O)[Si](C)(C)C1439.0Semi standard non polar33892256
N-Acetylthreonine,2TMS,isomer #1CC(=O)N[C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C1511.1Semi standard non polar33892256
N-Acetylthreonine,2TMS,isomer #2CC(=O)N([C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C)[Si](C)(C)C1522.7Semi standard non polar33892256
N-Acetylthreonine,2TMS,isomer #3CC(=O)N([C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O)[Si](C)(C)C1467.6Semi standard non polar33892256
N-Acetylthreonine,3TMS,isomer #1CC(=O)N([C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C)[Si](C)(C)C1567.5Semi standard non polar33892256
N-Acetylthreonine,3TMS,isomer #1CC(=O)N([C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C)[Si](C)(C)C1577.7Standard non polar33892256
N-Acetylthreonine,3TMS,isomer #1CC(=O)N([C@H](C(=O)O[Si](C)(C)C)[C@@H](C)O[Si](C)(C)C)[Si](C)(C)C1618.7Standard polar33892256
N-Acetylthreonine,1TBDMS,isomer #1CC(=O)N[C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C(C)(C)C1648.9Semi standard non polar33892256
N-Acetylthreonine,1TBDMS,isomer #2CC(=O)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O1635.1Semi standard non polar33892256
N-Acetylthreonine,1TBDMS,isomer #3CC(=O)N([C@H](C(=O)O)[C@@H](C)O)[Si](C)(C)C(C)(C)C1683.2Semi standard non polar33892256
N-Acetylthreonine,2TBDMS,isomer #1CC(=O)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C1934.2Semi standard non polar33892256
N-Acetylthreonine,2TBDMS,isomer #2CC(=O)N([C@H](C(=O)O)[C@@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1971.5Semi standard non polar33892256
N-Acetylthreonine,2TBDMS,isomer #3CC(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O)[Si](C)(C)C(C)(C)C1932.4Semi standard non polar33892256
N-Acetylthreonine,3TBDMS,isomer #1CC(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2205.0Semi standard non polar33892256
N-Acetylthreonine,3TBDMS,isomer #1CC(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2207.6Standard non polar33892256
N-Acetylthreonine,3TBDMS,isomer #1CC(=O)N([C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2081.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylthreonine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-1d2038b89692da4749cd2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylthreonine GC-MS (3 TMS) - 70eV, Positivesplash10-024u-9344000000-535eeae0147574da8de62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetylthreonine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 20V, Positive-QTOFsplash10-05fr-9100000000-3c15d1d8d68f1a7965232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 30V, Positive-QTOFsplash10-0a4i-9000000000-3b51aead01a04d6109a02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 30V, Negative-QTOFsplash10-00dl-9000000000-fdbccb95d44386e1d1a52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 40V, Negative-QTOFsplash10-0006-9000000000-7072d439f6589c40cb9f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 20V, Negative-QTOFsplash10-00di-9000000000-36c456db87ed51ca88802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 10V, Negative-QTOFsplash10-00di-9300000000-c59e1f6b7b2296f6ad1a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 0V, Positive-QTOFsplash10-0229-1900000000-a86fc91de4c0405170272021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 30V, Positive-QTOFsplash10-052f-9000000000-e50ba11b3f86dca9c8c32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 0V, Positive-QTOFsplash10-03di-2900000000-86b17a4013bd30e56cab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 10V, Positive-QTOFsplash10-0002-9100000000-46ba61bba8ee9f4a61482021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 30V, Positive-QTOFsplash10-0a4i-9000000000-d79d4a04defbc42905842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 10V, Positive-QTOFsplash10-00di-9600000000-5ad7e5d501555257a3ad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 10V, Positive-QTOFsplash10-00di-7900000000-2972d3f17d61fb0ed9ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - N-Acetylthreonine 40V, Positive-QTOFsplash10-0a4i-9000000000-965a8c0a9636a8724ed72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 10V, Positive-QTOFsplash10-0006-0900000000-c32d4033c8fd61a8c5aa2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 20V, Positive-QTOFsplash10-0fxy-3900000000-a7995b3f78d81ed455b12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 40V, Positive-QTOFsplash10-0f6t-9700000000-72bec44e7b7e910b16032017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 10V, Negative-QTOFsplash10-03xr-1900000000-265c5142fb5376e3a5422017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 20V, Negative-QTOFsplash10-014j-6900000000-f90c41a1366e693851372017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 40V, Negative-QTOFsplash10-0abc-9100000000-50328b9e8ed90ea07c882017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 10V, Negative-QTOFsplash10-0i00-2900000000-606f198cea758ab264082021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 20V, Negative-QTOFsplash10-0fxw-9800000000-5b2da7ce6b2a4af20aa82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 40V, Negative-QTOFsplash10-0006-9000000000-996228af0c7ea7edb5d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 10V, Positive-QTOFsplash10-00r6-2900000000-a19400d9592f5d1a96372021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetylthreonine 20V, Positive-QTOFsplash10-0fka-9500000000-0450cf4fbdcfa653bb872021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound152204
PDB IDNot Available
ChEBI ID45826
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sass JO, Mohr V, Olbrich H, Engelke U, Horvath J, Fliegauf M, Loges NT, Schweitzer-Krantz S, Moebus R, Weiler P, Kispert A, Superti-Furga A, Wevers RA, Omran H: Mutations in ACY1, the gene encoding aminoacylase 1, cause a novel inborn error of metabolism. Am J Hum Genet. 2006 Mar;78(3):401-9. Epub 2006 Jan 18. [PubMed:16465618 ]
  2. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  3. Tanaka H, Sirich TL, Plummer NS, Weaver DS, Meyer TW: An Enlarged Profile of Uremic Solutes. PLoS One. 2015 Aug 28;10(8):e0135657. doi: 10.1371/journal.pone.0135657. eCollection 2015. [PubMed:26317986 ]
  4. Van Damme P, Hole K, Pimenta-Marques A, Helsens K, Vandekerckhove J, Martinho RG, Gevaert K, Arnesen T: NatF contributes to an evolutionary shift in protein N-terminal acetylation and is important for normal chromosome segregation. PLoS Genet. 2011 Jul;7(7):e1002169. doi: 10.1371/journal.pgen.1002169. Epub 2011 Jul 7. [PubMed:21750686 ]
  5. Ree R, Varland S, Arnesen T: Spotlight on protein N-terminal acetylation. Exp Mol Med. 2018 Jul 27;50(7):1-13. doi: 10.1038/s12276-018-0116-z. [PubMed:30054468 ]
  6. Toyohara T, Akiyama Y, Suzuki T, Takeuchi Y, Mishima E, Tanemoto M, Momose A, Toki N, Sato H, Nakayama M, Hozawa A, Tsuji I, Ito S, Soga T, Abe T: Metabolomic profiling of uremic solutes in CKD patients. Hypertens Res. 2010 Sep;33(9):944-52. doi: 10.1038/hr.2010.113. Epub 2010 Jul 8. [PubMed:20613759 ]
  7. Vanholder R, Baurmeister U, Brunet P, Cohen G, Glorieux G, Jankowski J: A bench to bedside view of uremic toxins. J Am Soc Nephrol. 2008 May;19(5):863-70. doi: 10.1681/ASN.2007121377. Epub 2008 Feb 20. [PubMed:18287557 ]