You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
| Record Information |
|---|
| Version | 3.6 |
|---|
| Creation Date | 2005-11-16 15:48:42 UTC |
|---|
| Update Date | 2017-03-02 21:25:46 UTC |
|---|
| HMDB ID | HMDB00267 |
|---|
| Secondary Accession Numbers | None |
|---|
| Metabolite Identification |
|---|
| Common Name | Pyroglutamic acid |
|---|
| Description | Pyroglutamic acid is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid. Elevated blood levels may be associated with problems of glutamine or glutathione metabolism. This compound is found in substantial amounts in brain tissue and other tissue in bound form, especially skin. Also present in plant tissues. It is sold, over the counter, as a "smart drug" for improving blood circulation in the brain. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (-)-2-Pyrrolidone-5-carboxylic acid | ChEBI | | (S)-(-)-2-Pyrrolidone-5-carboxylic acid | ChEBI | | (S)-Pyroglutamic acid | ChEBI | | 5-Pyrrolidone-2-carboxylic acid | ChEBI | | L-5-Pyrrolidone-2-carboxylic acid | ChEBI | | L-Pyroglutamic acid | ChEBI | | Pidolic acid | ChEBI | | Pyroglutamate | ChEBI | | (-)-2-Pyrrolidone-5-carboxylate | Generator | | (S)-(-)-2-Pyrrolidone-5-carboxylate | Generator | | (S)-Pyroglutamate | Generator | | 5-Pyrrolidone-2-carboxylate | Generator | | L-5-Pyrrolidone-2-carboxylate | Generator | | L-Pyroglutamate | Generator | | Pidolate | Generator | | (-)-Pyroglutamate | HMDB | | (-)-Pyroglutamic acid | HMDB | | (5S)-2-Oxopyrrolidine-5-carboxylate | HMDB | | (5S)-2-Oxopyrrolidine-5-carboxylic acid | HMDB | | (S)-(-)-g-Butyrolactam-g-carboxylate | HMDB | | (S)-(-)-g-Butyrolactam-g-carboxylic acid | HMDB | | (S)-(-)-gamma-Butyrolactam-gamma-carboxylate | HMDB | | (S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid | HMDB | | (S)-2-Pyrrolidone-5-carboxylate | HMDB | | (S)-2-Pyrrolidone-5-carboxylic acid | HMDB | | (S)-5-oxo-2-Pyrrolidinecarboxylate | HMDB | | (S)-5-oxo-2-Pyrrolidinecarboxylic acid | HMDB | | 2-L-Pyrrolidone-5-carboxylate | HMDB | | 2-L-Pyrrolidone-5-carboxylic acid | HMDB | | 2-Oxopyrrolidine-5(S)-carboxylate | HMDB | | 2-Oxopyrrolidine-5(S)-carboxylic acid | HMDB | | 2-Pyrrolidinone-5-carboxylate | HMDB | | 2-Pyrrolidinone-5-carboxylic acid | HMDB | | 5-Carboxy-2-pyrrolidinone | HMDB | | 5-L-Oxoproline | HMDB | | 5-oxo-L-Proline | HMDB | | 5-Oxoproline | HMDB | | 5-Pyrrolidinone-2-carboxylate | HMDB | | 5-Pyrrolidinone-2-carboxylic acid | HMDB | | Ajidew a 100 | HMDB | | Glutimate | HMDB | | Glutimic acid | HMDB | | Glutiminate | HMDB | | Glutiminic acid | HMDB | | L-2-Pyrrolidone-5-carboxylate | HMDB | | L-2-Pyrrolidone-5-carboxylic acid | HMDB | | L-5-Carboxy-2-pyrrolidinone | HMDB | | L-5-oxo-2-Pyrrolidinecarboxylate | HMDB | | L-5-oxo-2-Pyrrolidinecarboxylic acid | HMDB | | L-5-Oxoproline | HMDB | | L-Glutamic acid g-lactam | HMDB | | L-Glutimate | HMDB | | L-Glutimic acid | HMDB | | L-Glutiminate | HMDB | | L-Glutiminic acid | HMDB | | L-Pyrrolidinonecarboxylate | HMDB | | L-Pyrrolidinonecarboxylic acid | HMDB | | L-Pyrrolidonecarboxylate | HMDB | | L-Pyrrolidonecarboxylic acid | HMDB | | Oxoproline | HMDB | | Oxopyrrolidinecarboxylate | HMDB | | Oxopyrrolidinecarboxylic acid | HMDB | | Pidolidone | HMDB | | Pyrrolidinonecarboxylate | HMDB | | Pyrrolidinonecarboxylic acid | HMDB | | Pyrrolidone-5-carboxylate | HMDB | | Pyrrolidone-5-carboxylic acid | HMDB | | Pyrrolidonecarboxylic acid | HMDB | | 5-Ketoproline | MeSH | | Pidolate, magnesium | MeSH | | 5-Oxopyrrolidine-2-carboxylic acid | MeSH | | Magnesium pidolate | MeSH |
|
|---|
| Chemical Formula | C5H7NO3 |
|---|
| Average Molecular Weight | 129.114 |
|---|
| Monoisotopic Molecular Weight | 129.042593095 |
|---|
| IUPAC Name | (2S)-5-oxopyrrolidine-2-carboxylic acid |
|---|
| Traditional Name | pyroglutamic acid |
|---|
| CAS Registry Number | 98-79-3 |
|---|
| SMILES | OC(=O)[C@@H]1CCC(=O)N1 |
|---|
| InChI Identifier | InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1 |
|---|
| InChI Key | ODHCTXKNWHHXJC-VKHMYHEASA-N |
|---|
| Chemical Taxonomy |
|---|
| Description | This compound belongs to the class of chemical entities 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), or a derivative thereof. |
|---|
| Kingdom | Chemical entities |
|---|
| Super Class | Organic compounds |
|---|
| Class | Organic acids and derivatives |
|---|
| Sub Class | Carboxylic acids and derivatives |
|---|
| Direct Parent | Alpha amino acids and derivatives |
|---|
| Alternative Parents | |
|---|
| Substituents | - Alpha-amino acid or derivatives
- Pyrroline carboxylic acid
- Pyrroline carboxylic acid or derivatives
- Pyrroline
- Cyclic carboximidic acid
- Lactim
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Azacycle
- Organoheterocyclic compound
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organic nitrogen compound
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
|
|---|
| Molecular Framework | Aliphatic heteromonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | - Component of Glutathione metabolism
- Essential amino acid
|
|---|
| Application | Not Available |
|---|
| Cellular locations | - Cytoplasm (predicted from logP)
|
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 476.0 mg/mL at 13 °C | Not Available | | LogP | Not Available | Not Available |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | |
|---|
| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0ab9-8900000000-f79dc90370ba38f587c9 | View in MoNA |
|---|
| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | Not Available |
|---|
| GC-MS | GC-MS Spectrum - GC-EI-TOF | splash10-0a4i-0900000000-90fb43273551aeb9b2c4 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-001i-9500000000-ebc64308ec5d5bdb303e | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-053r-9000000000-7377cb17491942e9589c | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-053u-9000000000-fcab1396867356ebd6ae | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-5b0c6536e1b3217b8544 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-c30ac0bd264c8007ef92 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-004i-5900000000-ea3a164653e4235716ae | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0f89-9000000000-f6620738e68f990d0594 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0udi-9000000000-7937bee2e9a6d6b29cbd | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-004i-0900000000-f20401903b234914b936 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-0900000000-9446bb65e0edd72cfd59 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0059-7900000000-74eccdeb9f0d5fd17614 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0f8a-9000000000-8786a9cd5e488192f34d | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0f6t-9000000000-ebcc1ac4acd525218e80 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-01q9-2900000000-754ae9b699ec1b22cd76 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-001i-9300000000-eabb8c4dc0d1111e0431 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00lr-9100000000-1dd17702aee7e5bce618 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-067i-9000000000-c9669794d3a8746be498 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-9e103abb0a6ed890051e | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-03e9-3900000000-da8cf252285c1d616586 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-01q9-9400000000-96a7fe5a81188c49d1ba | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-014i-9000000000-356215339a43217dea66 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-02vl-9000000000-ed47ec6e675eb338da19 | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-014i-9000000000-f647da344adbdf7bfb1b | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-9200000000-0bddc68d58c6fb981d1a | View in MoNA |
|---|
| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-004i-0900000000-c70c79fa828bbf137ebc | View in MoNA |
|---|
| 1D NMR | 1H NMR Spectrum | Not Available |
|---|
| 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
|---|
|
|---|
| Biological Properties |
|---|
| Cellular Locations | - Cytoplasm (predicted from logP)
|
|---|
| Biofluid Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
|
|---|
| Tissue Location | |
|---|
| Pathways | | Name | SMPDB Link | KEGG Link |
|---|
| 5-oxoprolinase deficiency | SMP00500 | Not Available | | 5-Oxoprolinuria | SMP00143 | Not Available | | Gamma-glutamyl-transpeptidase deficiency | SMP00501 | Not Available | | Gamma-Glutamyltransferase Deficiency | SMP00183 | Not Available | | Glutathione Metabolism | SMP00015 | map00480 | | Glutathione Synthetase Deficiency | SMP00337 | Not Available |
|
|---|
| Normal Concentrations |
|---|
| |
| Blood | Detected and Quantified | 19.5 +/- 3.7 uM | Adult (>18 years old) | Both | Normal | | details | | Blood | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 47 +/- 30 uM | Adult (>18 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 41.0 +/- 31.0 uM | Adult (>18 years old) | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Infant (0-1 year old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected and Quantified | 30.19 +/- 31.32 uM | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 47.641 +/- 19.524 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 40.428 +/- 19.331 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 21-30 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | | Urine | Detected and Quantified | 20.7 (10.2-32.6) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | <79.14 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 14.0 +/- 7.2 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 17-25 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 7.3 (0.1-29.3) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | | Urine | Detected and Quantified | 24.1 (3.4-54.2) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | | Urine | Detected and Quantified | 5.3 (2.9-10.4) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 3.1 (1.9-11.3) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 18.6 (4.5-24.9) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| |
| Blood | Detected and Quantified | 87.00 (13.00-161.00) uM | Adult (>18 years old) | Both | Glutathione synthetase deficiency | | details | | Blood | Detected but not Quantified | | Adult (>18 years old) | Both | Schizophrenia | | details | | Blood | Detected and Quantified | 3.5 (3.00-4.00) uM | Children (1-13 years old) | Both | Glutathione synthetase deficiency | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 2326.0 uM | Adult (>18 years old) | Both | Pyroglutamic aciduria | | details | | Feces | Detected but not Quantified | | Not Specified | Not Specified | Cryptosporidium infection | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Irritable bowel syndrome | | details | | Urine | Detected and Quantified | 28.8 (3.4-54.2) umol/mmol creatinine | Adult (>18 years old) | Both | 5-oxoprolinase deficiency | | details | | Urine | Detected and Quantified | 3500.0 (1000.0-6000.0) umol/mmol creatinine | Children (1-13 years old) | Both | 5-Oxoprolinase Deficiency | | details | | Urine | Detected and Quantified | 34.75 +/- 17.53 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Autosomal dominant polycystic kidney disease (ADPKD) | | details | | Urine | Detected and Quantified | 17000.00 (4000.00-30000.00) umol/mmol creatinine | Children (1-13 years old) | Both | Glutathione synthetase deficiency | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Schizophrenia | | details | | Urine | Detected and Quantified | 1.9 umol/mmol creatinine | Adult (>18 years old) | Both | Pyroglutamic aciduria | | details | | Urine | Detected and Quantified | 47.522 +/- 35.017 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | | Urine | Detected and Quantified | 80.794 +/- 83.738 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details |
|
|---|
| Associated Disorders and Diseases |
|---|
| Disease References | | Schizophrenia |
|---|
- Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
| | Glutathione synthetase deficiency |
|---|
- Jellum E, Stokke O, Eldjarn L: Combined use of gas chromatography, mass spectrometry, and computer in diagnosis and studies of metabolic disorders. Clin Chem. 1972 Aug;18(8):800-9. [PubMed:4557757 ]
- Wevers RA, Engelke U, Heerschap A: High-resolution 1H-NMR spectroscopy of blood plasma for metabolic studies. Clin Chem. 1994 Jul;40(7 Pt 1):1245-50. [PubMed:8013094 ]
- MetaGene [Link]
| | 5-oxoprolinase deficiency |
|---|
- MetaGene [Link]
|
|
|---|
| Associated OMIM IDs | - 181500 (Schizophrenia)
- 266130 (Glutathione synthetase deficiency)
- 260005 (5-oxoprolinase deficiency)
|
|---|
| External Links |
|---|
| DrugBank ID | DB03088 |
|---|
| DrugBank Metabolite ID | Not Available |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| Phenol Explorer Metabolite ID | Not Available |
|---|
| FoodDB ID | FDB014506 |
|---|
| KNApSAcK ID | C00007403 |
|---|
| Chemspider ID | 7127 |
|---|
| KEGG Compound ID | C01879 |
|---|
| BioCyc ID | CPD-589 |
|---|
| BiGG ID | 1800372 |
|---|
| Wikipedia Link | Pyroglutamic acid |
|---|
| NuGOwiki Link | HMDB00267 |
|---|
| Metagene Link | HMDB00267 |
|---|
| METLIN ID | 3251 |
|---|
| PubChem Compound | 7405 |
|---|
| PDB ID | PCA |
|---|
| ChEBI ID | 18183 |
|---|
| References |
|---|
| Synthesis Reference | Pumpor, Ksenia; Boettcher, Christoph; Fehn, Susanna; Burger, Klaus. Hexafluoroacetone as protecting and activating reagent: an efficient strategy for activation of pyroglutamic acid and homologs.Heterocycles (2003), 61 259-269. |
|---|
| Material Safety Data Sheet (MSDS) | Download (PDF) |
|---|
| General References | - 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
- Jellum E, Stokke O, Eldjarn L: Combined use of gas chromatography, mass spectrometry, and computer in diagnosis and studies of metabolic disorders. Clin Chem. 1972 Aug;18(8):800-9. [PubMed:4557757 ]
- Wevers RA, Engelke U, Heerschap A: High-resolution 1H-NMR spectroscopy of blood plasma for metabolic studies. Clin Chem. 1994 Jul;40(7 Pt 1):1245-50. [PubMed:8013094 ]
- Manning NJ, Davies NP, Olpin SE, Carpenter KH, Smith MF, Pollitt RJ, Duncan SL, Larsson A, Carlsson B: Prenatal diagnosis of glutathione synthase deficiency. Prenat Diagn. 1994 Jun;14(6):475-8. [PubMed:7937585 ]
- Caspers PJ, Lucassen GW, Carter EA, Bruining HA, Puppels GJ: In vivo confocal Raman microspectroscopy of the skin: noninvasive determination of molecular concentration profiles. J Invest Dermatol. 2001 Mar;116(3):434-42. [PubMed:11231318 ]
- Hussain Z, Lannigan R, Stoakes L: A new approach for presumptive identification of clinically important streptococci. Zentralbl Bakteriol Mikrobiol Hyg A. 1984 Oct;258(1):74-9. [PubMed:6441390 ]
- Creer MH, Lau BW, Jones JD, Chan KM: Pyroglutamic acidemia in an adult patient. Clin Chem. 1989 Apr;35(4):684-6. [PubMed:2702756 ]
- Hammond JW, Potter M, Truscott R, Wilcken B: gamma-Glutamylglutamine identified in plasma and cerebrospinal fluid from hyperammonaemic patients. Clin Chim Acta. 1990 Dec 24;194(2-3):173-83. [PubMed:2093471 ]
- Uhlhaas S, Lange H: Striatal deficiency of L-pyroglutamic acid in Huntington's disease is accompanied by increased plasma levels. Brain Res. 1988 Aug 2;457(1):196-9. [PubMed:2971422 ]
- Croal BL, Glen AC, Kelly CJ, Logan RW: Transient 5-oxoprolinuria (pyroglutamic aciduria) with systemic acidosis in an adult receiving antibiotic therapy. Clin Chem. 1998 Feb;44(2):336-40. [PubMed:9474033 ]
- Winslow JW, Shih A, Bourell JH, Weiss G, Reed B, Stults JT, Goldsmith LT: Human seminal relaxin is a product of the same gene as human luteal relaxin. Endocrinology. 1992 May;130(5):2660-8. [PubMed:1572287 ]
- Erasmus E, Mienie LJ, de Vries WN, de Wet WJ, Carlsson B, Larsson A: Prenatal analysis in two suspected cases of glutathione synthetase deficiency. J Inherit Metab Dis. 1993;16(5):837-43. [PubMed:8295398 ]
|
|---|