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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-03-25 20:09:52 UTC |
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HMDB ID | HMDB0001310 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Alanine |
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Description | Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. http://www.dcnutrition.com/AminoAcids/). Alanine can be found in some Gram-positive bacteria (PMID: 24752840 ). |
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Structure | |
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Synonyms | Value | Source |
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(2R)-2-Aminopropanoic acid | ChEBI | (R)-2-Aminopropanoic acid | ChEBI | (R)-Alanine | ChEBI | D-2-Aminopropionic acid | ChEBI | D-Ala | ChEBI | D-Alanin | ChEBI | D-alpha-Alanine | ChEBI | D-alpha-Aminopropionic acid | ChEBI | DAL | ChEBI | (2R)-2-Aminopropanoate | Generator | (R)-2-Aminopropanoate | Generator | D-2-Aminopropionate | Generator | D-a-Alanine | Generator | D-α-alanine | Generator | D-a-Aminopropionate | Generator | D-a-Aminopropionic acid | Generator | D-alpha-Aminopropionate | Generator | D-α-aminopropionate | Generator | D-α-aminopropionic acid | Generator | Alanine | HMDB, MeSH | D(-)-a -Alanine | HMDB | D(-)-alpha-Alanine | HMDB | D-(-)-Alanine | HMDB | (2R)-2-Aminopropionic acid | HMDB | (R)-2-Aminopropionic acid | HMDB | D(-)-α-Alanine | HMDB |
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Chemical Formula | C3H7NO2 |
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Average Molecular Weight | 89.0932 |
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Monoisotopic Molecular Weight | 89.047678473 |
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IUPAC Name | (2R)-2-aminopropanoic acid |
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Traditional Name | D-alanine |
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CAS Registry Number | 338-69-2 |
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SMILES | C[C@@H](N)C(O)=O |
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InChI Identifier | InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1 |
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InChI Key | QNAYBMKLOCPYGJ-UWTATZPHSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alanine and derivatives |
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Alternative Parents | |
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Substituents | - Alanine or derivatives
- Alpha-amino acid
- D-alpha-amino acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Organopnictogen compound
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Biological location: Source: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 292 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 165 mg/mL | Not Available | LogP | -2.912 | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-d31f7a2ed8284a740b59 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9500000000-d9aff70e7ddd0c94cf50 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-9000000000-597f42bcde0e9f005b7e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-ffef20b2a24280b6fac1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0007-9000000000-5494d4107e065019362a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-9000000000-536fa384ea61b8df326e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9000000000-447340852e905814000e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0006-9000000000-320cdf459ab1249aeead | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0006-9000000000-e42a8e9c2a1c69fb6bb2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0006-9000000000-2c2b7ae491c5edb0c9ca | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0006-9000000000-4832fe79b009c4a4841e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-0006-9000000000-b70e34a4340b1eba96fb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-536fa384ea61b8df326e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-447340852e905814000e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-000i-9000000000-4f17ee45605aa5062be3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-000i-9000000000-89574d659c7bde46108e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-a2eab41650cb9ab9ccd1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-a667a47345081b445cc9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-2c2b7ae491c5edb0c9ca | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-4832fe79b009c4a4841e | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-b70e34a4340b1eba96fb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-9000000000-080ffbbf05d95b7bcfe6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-0dfcc5cb0b7d9f01e04a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002f-9000000000-130c999fe6b63419cfa1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-2ddc0bb04bae8f928a23 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9000000000-98c403c9cd494594babf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-38a12affa4e4f4e91626 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Urine
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 444.61(116.67) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 448.89(115.71) uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 4.98-92.078 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 5.77-78.73 umol/mmol creatinine | Adolescent (13-18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 6.33-58.60 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 10.52-340.09 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 11.42-169.68 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 7.24-146.94 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 247.2 (89.1) uM | Adult (>18 years old) | Female | Down syndrome pregnancy | | details | Blood | Detected and Quantified | 231.9 (87.3) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 293.4 +/- 83.44 uM | Adult (>18 years old) | Female | Pregnancy with fetuses with trisomy 18 | | details | Blood | Detected and Quantified | 258.62 +/- 85.38 uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 263.8 (51.5) uM | Adult (>18 years old) | Female | Early preeclampsia | | details | Blood | Detected and Quantified | 332.1 (184.2) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 284.62 (65.96) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 267.32 (53.39) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 496.62(101.29) uM | Adult (>18 years old) | Both | Heart failure with preserved ejection fraction | | details | Blood | Detected and Quantified | 366.8 (204.8) uM | Adult (>18 years old) | Female | Late-onset preeclampsia | | details | Blood | Detected and Quantified | 323.8 (151.2) uM | Adult (>18 years old) | Female | Pregnancy | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 78 uM | Not Specified | Not Specified | propionic acidemia | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Early preeclampsia |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
| Pregnancy |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomics and first-trimester prediction of early-onset preeclampsia. J Matern Fetal Neonatal Med. 2012 Oct;25(10):1840-7. doi: 10.3109/14767058.2012.680254. Epub 2012 Apr 28. [PubMed:22494326 ]
- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester Down syndrome prediction. Am J Obstet Gynecol. 2013 May;208(5):371.e1-8. doi: 10.1016/j.ajog.2012.12.035. Epub 2013 Jan 8. [PubMed:23313728 ]
- Bahado-Singh RO, Akolekar R, Chelliah A, Mandal R, Dong E, Kruger M, Wishart DS, Nicolaides K: Metabolomic analysis for first-trimester trisomy 18 detection. Am J Obstet Gynecol. 2013 Jul;209(1):65.e1-9. doi: 10.1016/j.ajog.2013.03.028. Epub 2013 Mar 25. [PubMed:23535240 ]
- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Late-onset preeclampsia |
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- Bahado-Singh RO, Akolekar R, Mandal R, Dong E, Xia J, Kruger M, Wishart DS, Nicolaides K: First-trimester metabolomic detection of late-onset preeclampsia. Am J Obstet Gynecol. 2013 Jan;208(1):58.e1-7. doi: 10.1016/j.ajog.2012.11.003. Epub 2012 Nov 13. [PubMed:23159745 ]
| Propionic acidemia |
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- Scholl-Burgi S, Haberlandt E, Gotwald T, Albrecht U, Baumgartner Sigl S, Rauchenzauner M, Rostasy K, Karall D: Stroke-like episodes in propionic acidemia caused by central focal metabolic decompensation. Neuropediatrics. 2009 Apr;40(2):76-81. doi: 10.1055/s-0029-1231065. Epub 2009 Oct 6. [PubMed:19809936 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB01786 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022546 |
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KNApSAcK ID | C00019654 |
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Chemspider ID | 64234 |
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KEGG Compound ID | C00133 |
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BioCyc ID | D-ALANINE |
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BiGG ID | 33977 |
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Wikipedia Link | Alanine |
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METLIN ID | Not Available |
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PubChem Compound | 71080 |
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PDB ID | Not Available |
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ChEBI ID | 15570 |
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Food Biomarker Ontology | Not Available |
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VMH ID | ALA_D |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Hamase K, Konno R, Morikawa A, Zaitsu K: Sensitive determination of D-amino acids in mammals and the effect of D-amino-acid oxidase activity on their amounts. Biol Pharm Bull. 2005 Sep;28(9):1578-84. [PubMed:16141519 ]
- D'Aniello A, Vetere A, Fisher GH, Cusano G, Chavez M, Petrucelli L: Presence of D-alanine in proteins of normal and Alzheimer human brain. Brain Res. 1992 Oct 2;592(1-2):44-8. [PubMed:1450921 ]
- Fukushima T, Santa T, Homma H, Nagatomo R, Imai K: Determination of D-amino acids in serum from patients with renal dysfunction. Biol Pharm Bull. 1995 Aug;18(8):1130-2. [PubMed:8535409 ]
- Nagata Y, Masui R, Akino T: The presence of free D-serine, D-alanine and D-proline in human plasma. Experientia. 1992 Oct 15;48(10):986-8. [PubMed:1426150 ]
- Fisher GH, D'Aniello A, Vetere A, Padula L, Cusano GP, Man EH: Free D-aspartate and D-alanine in normal and Alzheimer brain. Brain Res Bull. 1991 Jun;26(6):983-5. [PubMed:1933416 ]
- Radkov AD, Moe LA: Bacterial synthesis of D-amino acids. Appl Microbiol Biotechnol. 2014 Jun;98(12):5363-74. doi: 10.1007/s00253-014-5726-3. Epub 2014 Apr 22. [PubMed:24752840 ]
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