| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:08:02 -0700 |
| HMDB ID |
HMDB00177 |
| Secondary Accession Numbers |
|
| Metabolite Identification |
| Common Name |
L-Histidine |
| Description |
Histidine is an essential amino acid for infants but not adults. Infants four to six months old require 33 mg/kg of histidine. It is not clear how adults make small amounts of histidine, and dietary sources probably account for most of the histidine in the body. Inborn errors of histidine metabolism exist and are marked by increased histidine levels in the blood. Elevated blood histidine is accompanied by a wide range of symptoms, from mental and physical retardation to poor intellectual functioning, emotional instability, tremor, ataxia and psychosis. Histidine in medical therapies has its most promising trials in rheumatoid arthritis where up to 4.5 g daily have been used effectively in severely affected patients. Arthritis patients have been found to have low serum histidine levels, apparently because of too-rapid removal of histidine from their blood. Histidine and other imidazole compounds have anti-inflammatory properties. histidine may accomplish this function through a complex interaction with threonine or cysteine and possibly copper. However, copper is usually elevated in rheumatoid arthritis patients and worsens the disease. Other patients besides arthritis patients that have been found to be low in serum histidine are those with chronic renal failure. Histidine has been claimed to have been useful in hypertension because of its vasodilatory effects. Claims of its use to improve libido and counteract allergy are without proof at present. Histidine may have many other possible functions because it is the precursor of the ubiquitous neurohormone-neurotransmitter histamine. Histidine increases histamine in the blood and probably in the brain. Low blood histamine with low serum histidine occurs in rheumatoid arthritis patients. Low blood histamine also occurs in some manic, schizophrenic, high copper and hyperactive groups of psychiatric patients. Histidine is a useful therapy in all low histamine patients. ( http://www.dcnutrition.com ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (S)-1H-Imidazole-4-alanine
- (S)-2-Amino-3-(4-imidazolyl)propionsaeure
- (S)-4-(2-Amino-2-carboxyethyl)imidazole
- (S)-a-Amino-1H-imidazole-4-propanoate
- (S)-a-Amino-1H-imidazole-4-propanoic acid
- (S)-alpha-Amino-1H-imidazole-4-propanoate
- (S)-alpha-Amino-1H-imidazole-4-propanoic acid
- (S)-alpha-Amino-1H-imidazole-4-propionate
- (S)-alpha-Amino-1H-imidazole-4-propionic acid
- (S)-Histidine
- (S)1H-Imidazole-4-alanine
- 3-(1H-Imidazol-4-yl)-L-Alanine
- Amino-1H-imidazole-4-propanoate
- Amino-1H-imidazole-4-propanoic acid
- Amino-4-imidazoleproprionate
- Amino-4-imidazoleproprionic acid
- Glyoxaline-5-alanine
- His
- Histidine
- L-(-)-Histidine
|
| Chemical Formula |
C6H9N3O2 |
| Average Molecular Weight |
155.1546 |
| Monoisotopic Molecular Weight |
155.069476547 |
| IUPAC Name |
(2S)-2-amino-3-(1H-imidazol-4-yl)propanoic acid |
| Traditional IUPAC Name |
histidine |
| CAS Registry Number |
71-00-1 |
| SMILES |
N[C@@H](CC1=CNC=N1)C(O)=O |
| InChI Identifier |
InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m0/s1 |
| InChI Key |
HNDVDQJCIGZPNO-YFKPBYRVSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Amino Acids, Peptides, and Analogues |
| Class |
Amino Acids and Derivatives |
| Sub Class |
Alpha Amino Acids and Derivatives |
| Other Descriptors |
- Aromatic Heteromonocyclic Compounds
- alpha-amino acid(ChEBI)
- imidazoles(ChEBI)
|
| Substituents |
- Aminoimidazole
- Carboxylic Acid
- Imidazole
- Imidazolyl Carboxylic Acid Derivative
- Primary Aliphatic Amine (Alkylamine)
|
| Direct Parent |
Alpha Amino Acids and Derivatives |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Aminoacyl-tRNA biosynthesis
- Component of Histidine metabolism
- Component of Nitrogen metabolism
- Essential amino acid
- Essential amino acids
- semi-essential amino acids
|
| Application |
Not Available |
| Cellular locations |
|
| Physical Properties |
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
287 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
45.6 mg/mL |
Not Available |
| LogP |
-3.32 |
CHMELIK,J ET AL. (1991) |
|
| Predicted Properties |
|
| Spectra |
|
| Gas-MS Spectrum |
| 1H NMR Spectrum |
| 13C NMR Spectrum |
| MS/MS Spectrum Quattro_QQQ 10 |
| MS/MS Spectrum Quattro_QQQ 25 |
| MS/MS Spectrum Quattro_QQQ 40 |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) |
| [1H,13C] 2D NMR Spectrum |
|
| Biological Properties |
| Cellular Locations |
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
- Saliva
- Urine
|
| Tissue Location |
|
| Pathways |
|
| Normal Concentrations |
|
| Blood |
Detected and Quantified |
|
75.0 +/- 20.0 uM |
Newborn (0-30 days old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
86.0 +/- 10.0 uM |
Children (1-13 year old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
89.0 +/- 11.0 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
83.0 +/- 14.0 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
143.1 +/- 27.3 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
82.0 (72.0-92.0) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
131.2 +/- 37.3 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
14.0 +/- 8.0 uM |
Not Specified |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
20.7 +/- 7.5 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
16.8 +/- 2.7 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
18.6 +/- 3.3 uM |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
16.4 +/- 6.1 uM |
Adult (>18 years old) |
Not Specified |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
10.9 (10.4-11.4) uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
11.9 +/- 1.7 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Saliva |
Detected and Quantified |
|
>10 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
101.9 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
25.79-212.81 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
87.2 (23.0-151.0) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
47.12 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
0.0036 - 0.0376 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
43 (17-90) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
urine by NMR
|
| Urine |
Detected and not Quantified |
|
Not Applicable |
Adult (>18 years old) |
Both |
Normal |
Urine compound detected by GC-MS
|
| Urine |
Detected and Quantified |
|
2.2 (1.18-3.4) umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
31.0 +/- 15.0 umol/mmol creatinine |
Children (1-13 year old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
85.0 +/- 33.0 umol/mmol creatinine |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
62.0 +/- 28.0 umol/mmol creatinine |
Adult (>18 years old) |
Female |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
60.75 +/- 27.45 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
45.6 (21.7-71.5) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
by LC-MS/MS (Biocrates kit)
|
| Urine |
Detected and Quantified |
|
88 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
194.90 +/- 144.31 umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|
| Blood |
Detected and Quantified |
|
46.1 +/- 17.5 uM |
Adult (>18 years old) |
Not Specified |
Heart Transplant |
Not Available |
| Blood |
Detected and Quantified |
|
88.00 (56.00-120.00) uM |
Adult (>18 years old) |
Both |
Histidinemia |
Not Available |
| Blood |
Detected and Quantified |
|
885.00 (290.00-1420.00) uM |
Adult (>18 years old) |
Both |
Histidinemia |
Not Available |
| Blood |
Detected and Quantified |
|
116.68 +/- 18.15 uM |
Elderly (>65 years old) |
Both |
Alzheimer's disease |
Not Available |
| Blood |
Detected and Quantified |
|
67.0 (64.0-70.0) uM |
Adult (>18 years old) |
Both |
Dengue fever |
Not Available |
| Blood |
Detected and Quantified |
|
80.5 +/- 4.2 uM |
Adult (>18 years old) |
Both |
Epilepsy |
Acute seizures
|
| Blood |
Detected and Quantified |
|
107.0 +/- 6.5 uM |
Adult (>18 years old) |
Both |
Epilepsy |
Refractory localization-related epilepsy (RLE)
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
21.4 +/- 6.6 uM |
Children (1-13 year old) |
Not Specified |
Leukemia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
10.3 +/- 3.7 uM |
Children (1-13 year old) |
Not Specified |
Leukemia |
Acute Lymphoblastic Leukemia (ALL) with Central...
|
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
13.00 uM |
Adult (>18 years old) |
Both |
Histidinemia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
95.00 (48.00-142.00) uM |
Adult (>18 years old) |
Both |
Histidinemia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
130.0 uM |
Adult (>18 years old) |
Both |
Histidinemia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
14.4 +/- 6.32 uM |
Adult (>18 years old) |
Both |
Probable Alzheimer's diesease |
Not Available |
| Urine |
Detected and Quantified |
|
0.0033 - 0.0186 umol/mmol creatinine |
Adult (>18 years old) |
Both |
ADPKD |
Not Available |
| Urine |
Detected and Quantified |
|
30.5 +/- 4.3 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Alzheimer's disease |
Not Available |
| Urine |
Detected and Quantified |
|
112.00 (59.00-166.00) umol/mmol creatinine |
Adult (>18 years old) |
Both |
Histidinuria |
Not Available |
| Urine |
Detected and Quantified |
|
105.3 +/- 12.7 umol/mmol creatinine |
Adult (>18 years old) |
Both |
3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency |
Not Available |
| Urine |
Detected and Quantified |
|
65.5 +/- 11.3 umol/mmol creatinine |
Adult (>18 years old) |
Both |
3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency |
Not Available |
| Urine |
Detected and Quantified |
|
52.9 +/- 12.5 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Arginosuccinic aciduria |
Not Available |
| Urine |
Detected and Quantified |
|
154.3 +/- 13.7 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Propionic acidemia |
Not Available |
| Urine |
Detected and Quantified |
|
52 +/- 29 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Tyrosinemia I |
Not Available |
| Urine |
Detected and Quantified |
|
37.9 +/- 9.8 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Tyrosinemia I |
Not Available |
| Urine |
Detected and Quantified |
|
62.6 +/- 12.3 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Phenylketonuria |
Not Available |
| Urine |
Detected and Quantified |
|
68 +/- 19.9 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Phenylketonuria |
Not Available |
| Urine |
Detected and Quantified |
|
171.8 +/- 4.3 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Maple syrup urine disease |
Not Available |
| Urine |
Detected and Quantified |
|
180.1 +/- 12.4 umol/mmol creatinine |
Adult (>18 years old) |
Both |
Aminoaciduria |
Not Available |
|
| Associated Disorders and Diseases |
| Disease References |
| Dengue fever |
- Klassen P, Furst P, Schulz C, Mazariegos M, Solomons NW: Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. Am J Clin Nutr. 2001 Mar;73(3):647-52.
Pubmed: 11237944
|
| Epilepsy |
- 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
|
| Histidinemia |
- Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51.
Pubmed: 7729054
- http://www.metagene.de/program/d.prg?mp=HISTIDINEMIA
- http://www.metagene.de/program/d.prg?mp=HISTIDINURIA
|
| Leukemia |
- 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
|
| Alzheimer's disease |
- Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10.
Pubmed: 17031479
|
|
| Associated OMIM IDs |
|
| External Links |
| DrugBank ID |
DB00117  |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB011856 |
| KNApSAcK ID |
C00001363  |
| Chemspider ID |
6038  |
| KEGG Compound ID |
C00135  |
| BioCyc ID |
HIS  |
| BiGG ID |
33985  |
| Wikipedia Link |
L-Histidine  |
| NuGOwiki Link |
HMDB00177  |
| Metagene Link |
HMDB00177  |
| METLIN ID |
21  |
| PubChem Compound |
6274  |
| PDB ID |
1KAH  |
| ChEBI ID |
15971  |
| References |
| Synthesis Reference |
Aurelio Luigi; Brownlee Robert T C; Hughes Andrew B A novel synthesis of N-methyl asparagine, arginine, histidine, and tryptophan. Organic letters (2002), 4(21), 3767-9. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- Mukerji SK, Pimstone NR, Gandhi SN, Tan KT: Biochemical diagnosis and monitoring therapeutic modulation of disease activity in an unusual case of congenital erythropoietic porphyria. Clin Chem. 1985 Dec;31(12):1946-51.
Pubmed: 4064282
- 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
- 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
- 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
- Xiao B, Jing C, Kelly G, Walker PA, Muskett FW, Frenkiel TA, Martin SR, Sarma K, Reinberg D, Gamblin SJ, Wilson JR: Specificity and mechanism of the histone methyltransferase Pr-Set7. Genes Dev. 2005 Jun 15;19(12):1444-54. Epub 2005 Jun 2.
Pubmed: 15933069
- Churchill D, Yacoub JM, Siu KP, Symes A, Gault MH: Toxic nephropathy after low-dose methoxyflurane anesthesia: drug interaction with secobarbital? Can Med Assoc J. 1976 Feb 21;114(4):326-8, 333.
Pubmed: 1253070
- Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51.
Pubmed: 7729054
- Sieja K, Stanosz S, von Mach-Szczypinski J, Olewniczak S, Stanosz M: Concentration of histamine in serum and tissues of the primary ductal breast cancers in women. Breast. 2005 Jun;14(3):236-41. Epub 2005 Jan 21.
Pubmed: 15927833
- 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
- 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
- Masini E, Fabbroni V, Giannini L, Vannacci A, Messerini L, Perna F, Cortesini C, Cianchi F: Histamine and histidine decarboxylase up-regulation in colorectal cancer: correlation with tumor stage. Inflamm Res. 2005 Apr;54 Suppl 1:S80-1.
Pubmed: 15928846
- Klassen P, Furst P, Schulz C, Mazariegos M, Solomons NW: Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. Am J Clin Nutr. 2001 Mar;73(3):647-52.
Pubmed: 11237944
- 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
- Xiao YP, Han CB, Mao XY, Li JY, Xu L, Ren CS, Xin Y: Relationship between abnormality of FHIT gene and EBV infection in gastric cancer. World J Gastroenterol. 2005 Jun 7;11(21):3212-6.
Pubmed: 15929169
- Mason AB, Halbrooks PJ, James NG, Connolly SA, Larouche JR, Smith VC, MacGillivray RT, Chasteen ND: Mutational analysis of C-lobe ligands of human serum transferrin: insights into the mechanism of iron release. Biochemistry. 2005 Jun 7;44(22):8013-21.
Pubmed: 15924420
- Janknecht R, Hipskind RA, Houthaeve T, Nordheim A, Stunnenberg HG: Identification of multiple SRF N-terminal phosphorylation sites affecting DNA binding properties. EMBO J. 1992 Mar;11(3):1045-54.
Pubmed: 1547771
- 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
- 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
|