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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 | 2006-05-22 15:12:05 UTC |
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| Update Date | 2020-02-26 21:24:14 UTC |
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| HMDB ID | HMDB0002712 |
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| Secondary Accession Numbers | - HMDB0011726
- HMDB0011736
- HMDB02712
- HMDB11726
- HMDB11736
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| Metabolite Identification |
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| Common Name | 1,5-Anhydrosorbitol |
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| Description | 1,5-Anhydrosorbitol or 1,5-anhydroglucitol (1,5-AG) is a validated marker of short-term glycemic control. This substance is derived mainly from food, is well absorbed in the intestine, and is distributed to all organs and tissues. It is metabolically stable, being excreted in the urine when its level exceeds the renal threshold. It is reabsorbed in the renal tubules and is competitively inhibited by glucosuria, which leads to a reduction in its level in serum. The correlation between this reduction and the amount of glucose present in urine is so close that 1,5 AG can be used as a sensitive, day-to-day, real-time marker of glycemic control. It provides useful information on current glycemic control and is superior to both hemoglobin A1C and fructosamine in detecting near-normoglycemia. 1,5-AG in human plasma has been proposed for several years as a short-term, retrospective marker of glycemic control and seems to be the most suitable parameter for monitoring glucose excursions. The decrease in serum 1,5-AG is very sensitive to urinary glucose excretion. It is a metabolically inert polyol that competes with glucose for reabsorption in the kidneys. Otherwise stable levels of 1,5-AG are rapidly depleted as blood glucose levels exceed the renal threshold for glucosuria. 1,5-AG is also more tightly associated with glucose fluctuations and postprandial glucose (PMID: 18088226 , 12166605 , 7783360 , 8940824 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1,5-Anhydro-D-sorbitol | ChEBI | | 1,5-Anhydroglucitol | ChEBI | | 1,5-AG | HMDB | | 1,5-Anhydro-D-glucitol | HMDB | | 1-Deoxyglucose | HMDB | | Aceritol | HMDB | | Polygalitol | HMDB | | 1-Deoxy-D-glucose | HMDB | | 1,5-Sorbitan | HMDB | | 1-Deoxy-D-glucopyranose | HMDB | | 1,5-ANHYDROSORBITOL | ChEBI |
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| Chemical Formula | C6H12O5 |
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| Average Molecular Weight | 164.1565 |
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| Monoisotopic Molecular Weight | 164.068473494 |
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| IUPAC Name | (2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol |
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| Traditional Name | 1,5-anhydroglucitol |
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| CAS Registry Number | 154-58-5 |
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| SMILES | OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3-,4+,5+,6+/m0/s1 |
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| InChI Key | MPCAJMNYNOGXPB-SLPGGIOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Monosaccharides |
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| Alternative Parents | |
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| Substituents | - Oxane
- Monosaccharide
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Ether
- Dialkyl ether
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Source: Biological location: |
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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 | 142 - 143 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | 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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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-00kb-0930000000-3e9a279cc11867623df9 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00kb-0930000000-3e9a279cc11867623df9 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0gb9-0900000000-3b72b858c9bcc30c45b1 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fr2-0920000000-5ad690bbbd7fce791cce | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9600000000-614246ddd5b68d2ed62d | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-01di-4169300000-4fef5d885796ecad0f89 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-014i-6900000000-9a919af22cbe7d86b80d | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-9100000000-f5cab1c2b02d65ad346a | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-014i-9000000000-ced7163dcc8f3ebdbbce | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-0w30-0900000000-7cd7be2b3ef8c9d328e3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-0900000000-c8a9b1625a999852f120 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00kb-1900000000-60691e9a1518b8f9eacd | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00bi-9200000000-e9e5be081f31a0ee52fd | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0900000000-c6502965757c84521bf7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03dj-1900000000-944d7cc4495151774511 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006x-9100000000-eea65e515404cb15787a | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm (predicted from logP)
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| Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Saliva
- Sweat
- Urine
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 130.0 (95.0 - 178.0) uM | Adolescent (13-18 years old) | Male | Normal | | details | | Blood | Detected and Quantified | 150.0 (140 - 171) uM | Adolescent (13-18 years old) | Female | Normal | | details | | Blood | Detected and Quantified | 150.0 (73.0 - 243.0) uM | Adult (>18 years old) | Not Specified | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 53.0 (11.0-95.0) uM | Adult (>18 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 25.0 +/- 13.0 uM | Adult (>18 years old) | Both | Normal | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 110.9 +/- 30.2 uM | Adult (>18 years old) | Both | 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 | | Sweat | Detected but not Quantified | | Adult | Both | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected and Quantified | 30.0 (9.7 - 66.4) uM | Adolescent (13-18 years old) | Both | Diabetes | | details | | Blood | Detected and Quantified | 62.0 +/- 38.0 uM | Adult (>18 years old) | Both | Diabetes | | details | | Blood | Detected but not Quantified | | Adult (>18 years old) | Both | Pancreatic Cancer | | details | | Blood | Detected and Quantified | 50.0 (18.5 - 95.0) uM | Adult (>18 years old) | Not Specified | Diabetes | | details | | Cerebrospinal Fluid (CSF) | Detected and Quantified | 41.7 +/-13.7 uM | Adult (>18 years old) | Both | Alzheimer's disease | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Attachment loss | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Missing teeth | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Male | Periodontal Probing Depth | | details | | Urine | Detected but not Quantified | | Adult (>18 years old) | Both | Bladder cancer | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Diabetes mellitus type 2 |
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- Dungan KM, Buse JB, Largay J, Kelly MM, Button EA, Kato S, Wittlin S: 1,5-anhydroglucitol and postprandial hyperglycemia as measured by continuous glucose monitoring system in moderately controlled patients with diabetes. Diabetes Care. 2006 Jun;29(6):1214-9. [PubMed:16731998 ]
- Stickle D, Turk J: A kinetic mass balance model for 1,5-anhydroglucitol: applications to monitoring of glycemic control. Am J Physiol. 1997 Oct;273(4 Pt 1):E821-30. [PubMed:9357814 ]
- Nguyen TM, Rodriguez LM, Mason KJ, Heptulla RA: Serum 1,5-anhydroglucitol (Glycomark) levels in children with and without type 1 diabetes mellitus. Pediatr Diabetes. 2007 Aug;8(4):214-9. [PubMed:17659063 ]
| | Pancreatic cancer |
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- Xie G, Lu L, Qiu Y, Ni Q, Zhang W, Gao YT, Risch HA, Yu H, Jia W: Plasma metabolite biomarkers for the detection of pancreatic cancer. J Proteome Res. 2015 Feb 6;14(2):1195-202. doi: 10.1021/pr501135f. Epub 2014 Dec 8. [PubMed:25429707 ]
| | Alzheimer's disease |
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- Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]
| | Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| | Missing teeth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| | Periodontal Probing Depth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB023050 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 58485 |
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| KEGG Compound ID | C07326 |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | 1,5-Anhydroglucitol |
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| METLIN ID | 3775 |
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| PubChem Compound | 64960 |
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| PDB ID | Not Available |
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| ChEBI ID | 16070 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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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 | - Sode K, Sugiura H, Tsugawa W, Watazu Y, Hamafuji T: Enzyme electrochemical preparation of a 3-keto derivative of 1,5-anhydro-D-glucitol using glucose-3-dehydrogenase. Appl Biochem Biotechnol. 2000 Spring;84-86:947-54. [PubMed:10849848 ]
- Yoshioka S, Saitoh S, Fujisawa T, Fujimori A, Takatani O, Funabashi M: Identification and metabolic implication of 1-deoxyglucose (1,5-anhydroglucitol) in human plasma. Clin Chem. 1982 Jun;28(6):1283-6. [PubMed:7074934 ]
- Servo C, Pitkanen E: Variation in polyol levels in cerebrospinal fluid and serum in diabetic patients. Diabetologia. 1975 Dec;11(6):575-80. [PubMed:1205026 ]
- Yamanouchi T, Minoda S, Ogata N, Tachibana Y, Sekino N, Miyashita H, Akaoka I: Prolonged hyperalimentation as a possible cause of renal tubular dysfunction: evaluation of 1,5-anhydro-D-glucitol resorption and N-acetylglucosaminidase excretion in humans. Clin Sci (Lond). 1995 Feb;88(2):203-10. [PubMed:7720346 ]
- Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]
- Dworacka M, Winiarska H, Szymanska M, Kuczynski S, Szczawinska K, Wierusz-Wysocka B: 1,5-anhydro-D-glucitol: a novel marker of glucose excursions. Int J Clin Pract Suppl. 2002 Jul;(129):40-4. [PubMed:12166605 ]
- Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
- Akanuma Y, Morita M, Fukuzawa N, Yamanouchi T, Akanuma H: Urinary excretion of 1,5-anhydro-D-glucitol accompanying glucose excretion in diabetic patients. Diabetologia. 1988 Nov;31(11):831-5. [PubMed:3234638 ]
- 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 ]
- Dungan KM: 1,5-anhydroglucitol (GlycoMark) as a marker of short-term glycemic control and glycemic excursions. Expert Rev Mol Diagn. 2008 Jan;8(1):9-19. [PubMed:18088226 ]
- Matsuyama T, Katayama Y, Fujita S: [Recent progress in evaluation of glycemic control by glycated protein and 1,5-AG]. Rinsho Byori. 1995 May;43(5):445-8. [PubMed:7783360 ]
- Saito H, Ohtomo T, Inui K: Na(+)-dependent uptake of 1,5-anhydro-D-glucitol via the transport systems for D-glucose and D-mannose in the kidney epithelial cell line, LLC-PK1. Nihon Jinzo Gakkai Shi. 1996 Oct;38(10):435-40. [PubMed:8940824 ]
- 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 ]
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