Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:12:07 UTC |
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NP-MRD ID | NP0000014 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Trehalose |
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Description | Trehalose, also known as alpha-D-trehalose or (GLC)2, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon. Trehalose is an extremely weak basic (essentially neutral) compound (based on its pKa). Trehalose exists in all living species, ranging from bacteria to humans. Trehalose can be converted into β-D-glucose and α-D-glucose; which is mediated by the enzyme trehalase. In humans, trehalose is involved in trehalose degradation. Outside of the human body, Trehalose has been detected, but not quantified in, a few different foods, such as bitter gourds, garden tomato, and mushrooms. This could make trehalose a potential biomarker for the consumption of these foods. |
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Structure | |
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Synonyms | Value | Source |
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(GLC)2 | ChEBI | alpha,Alpha'-trehalose | ChEBI | alpha-D-GLCP-(11)-alpha-D-GLCP | ChEBI | alpha-D-Glucopyranosyl-alpha-D-glucopyranoside | ChEBI | alpha-D-Trehalose | ChEBI | alpha-Trehalose | ChEBI | D-(+)-Trehalose | ChEBI | Ergot sugar | ChEBI | Mycose | ChEBI | a,Alpha'-trehalose | Generator | Α,alpha'-trehalose | Generator | a-D-GLCP-(11)-a-D-GLCP | Generator | Α-D-GLCP-(11)-α-D-GLCP | Generator | a-D-Glucopyranosyl-a-D-glucopyranoside | Generator | Α-D-glucopyranosyl-α-D-glucopyranoside | Generator | a-D-Trehalose | Generator | Α-D-trehalose | Generator | a-Trehalose | Generator | Α-trehalose | Generator | alpha,alpha-Trehalose | HMDB | D-Trehalose-anhydrous | HMDB | delta-Trehalose-anhydrous | HMDB | D-Trehalose | HMDB | Natural trehalose | HMDB | O-D-Glucopyranosyl-(1→1)-D-glucopyranoside | HMDB | alpha,Alpha'-D-trehalose | HMDB | alpha-D-Glucopyranosyl alpha-D-glucopyranoside | HMDB | Α,α'-D-trehalose | HMDB | Α,α-trehalose | HMDB | Α,α’-D-trehalose | HMDB | Α-D-glucopyranosyl α-D-glucopyranoside | HMDB | Trehalose | HMDB |
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Chemical Formula | C12H22O11 |
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Average Molecular Weight | 342.2965 |
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Monoisotopic Molecular Weight | 342.116211546 |
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IUPAC Name | (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol |
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Traditional Name | α,α'-trehalose |
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CAS Registry Number | 99-20-7 |
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SMILES | OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 |
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InChI Key | HDTRYLNUVZCQOY-LIZSDCNHSA-N |
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Spectra |
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| | Species of Origin |
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Species | Animalia; Eubacteria; Fungi |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. |
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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 | O-glycosyl compounds |
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Alternative Parents | |
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Substituents | - O-glycosyl compound
- Disaccharide
- Oxane
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- 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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 203 °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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General References | - Potier M, Dallaire L, Melancon SB: Occurrence and properties of fetal intestinal glycosidases (disaccharidases) in human amniotic fluid. Biol Neonate. 1975;27(3-4):141-52. [PubMed:241430 ]
- Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [PubMed:2229345 ]
- Yoshioka S, Aso Y: A quantitative assessment of the significance of molecular mobility as a determinant for the stability of lyophilized insulin formulations. Pharm Res. 2005 Aug;22(8):1358-64. Epub 2005 Aug 3. [PubMed:16078146 ]
- Guo N, Puhlev I, Brown DR, Mansbridge J, Levine F: Trehalose expression confers desiccation tolerance on human cells. Nat Biotechnol. 2000 Feb;18(2):168-71. [PubMed:10657122 ]
- Nie Y, de Pablo JJ, Palecek SP: Platelet cryopreservation using a trehalose and phosphate formulation. Biotechnol Bioeng. 2005 Oct 5;92(1):79-90. [PubMed:15937943 ]
- Fujita Y, Naka T, Doi T, Yano I: Direct molecular mass determination of trehalose monomycolate from 11 species of mycobacteria by MALDI-TOF mass spectrometry. Microbiology. 2005 May;151(Pt 5):1443-52. [PubMed:15870454 ]
- Lu FQ, Liu JH, Ouyang XL, Li XJ, Zhou J, Zhuang Y: [Process of human platelets loaded with rehalose before lyophilization]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2006 Feb;14(1):156-61. [PubMed:16584614 ]
- Shirkhanzadeh M: Microneedles coated with porous calcium phosphate ceramics: effective vehicles for transdermal delivery of solid trehalose. J Mater Sci Mater Med. 2005 Jan;16(1):37-45. [PubMed:15754142 ]
- Eroglu A, Russo MJ, Bieganski R, Fowler A, Cheley S, Bayley H, Toner M: Intracellular trehalose improves the survival of cryopreserved mammalian cells. Nat Biotechnol. 2000 Feb;18(2):163-7. [PubMed:10657121 ]
- Arguelles JC, Rodriguez T, Alvarez-Peral FJ: Trehalose hydrolysis is not required for human serum-induced dimorphic transition in Candida albicans: evidence from a tps1/tps1 mutant deficient in trehalose synthesis. Res Microbiol. 1999 Oct;150(8):521-9. [PubMed:10577485 ]
- Corning BF, Murphy JC, Fox JG: Group G streptococcal lymphadenitis in rats. J Clin Microbiol. 1991 Dec;29(12):2720-3. [PubMed:1757539 ]
- Davies JE, Sarkar S, Rubinsztein DC: Trehalose reduces aggregate formation and delays pathology in a transgenic mouse model of oculopharyngeal muscular dystrophy. Hum Mol Genet. 2006 Jan 1;15(1):23-31. Epub 2005 Nov 25. [PubMed:16311254 ]
- Ma X, Jamil K, Macrae TH, Clegg JS, Russell JM, Villeneuve TS, Euloth M, Sun Y, Crowe JH, Tablin F, Oliver AE: A small stress protein acts synergistically with trehalose to confer desiccation tolerance on mammalian cells. Cryobiology. 2005 Aug;51(1):15-28. [PubMed:15963489 ]
- Alcoba-Florez J, Mendez-Alvarez S, Cano J, Guarro J, Perez-Roth E, del Pilar Arevalo M: Phenotypic and molecular characterization of Candida nivariensis sp. nov., a possible new opportunistic fungus. J Clin Microbiol. 2005 Aug;43(8):4107-11. [PubMed:16081957 ]
- Chang L, Shepherd D, Sun J, Ouellette D, Grant KL, Tang XC, Pikal MJ: Mechanism of protein stabilization by sugars during freeze-drying and storage: native structure preservation, specific interaction, and/or immobilization in a glassy matrix? J Pharm Sci. 2005 Jul;94(7):1427-44. [PubMed:15920775 ]
- Sasnoor LM, Kale VP, Limaye LS: A combination of catalase and trehalose as additives to conventional freezing medium results in improved cryoprotection of human hematopoietic cells with reference to in vitro migration and adhesion properties. Transfusion. 2005 Apr;45(4):622-33. [PubMed:15819685 ]
- Alvarez-Peral FJ, Arguelles JC: Changes in external trehalase activity during human serum-induced dimorphic transition in Candida albicans. Res Microbiol. 2000 Dec;151(10):837-43. [PubMed:11191809 ]
- Berlutti F, Thaller MC, Dainelli B, Pezzi R: T-mod pathway, a reduced sequence for identification of gram-negative urinary tract pathogens. J Clin Microbiol. 1989 Jul;27(7):1646-9. [PubMed:2768451 ]
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