Tris - Wikipedia, the free encyclopedia

http://en.wikipedia.org/wiki/Tris

Tris
From Wikipedia, the free encyclopedia

Tris (also known as THAM) is an abbreviation of the organic compound known as tris(hydroxymethyl)aminomethane, with the formula (HOCH2)3CNH2. Tris is extensively used in biochemistry and molecular biology.[1] In biochemistry, Tris is widely used as a component of buffer solutions, such as in TAE and TBE buffer, especially for solutions of nucleic acids. It is a primary amine and thus undergoes the reactions associated with typical amines, e.g. condensations with aldehydes.

Tris

IUPAC name

Contents
1 Buffering features 1.1 Buffer details 1.2 Buffer inhibition 2 Preparation 3 Uses 3.1 Medical 4 See also 5 References

2-Amino-2-hydroxymethyl-propane-1,3-diol Other names TRIS, Tris, Tris base, Tris buffer, TrizmaTM, Trisamine, THAM, Tromethamine, Trometamol, Tromethane

Identifiers CAS number PubChem 77-86-1 6503

ChemSpider 6257

Buffering features
Tris has a pKa of 8.07 at 25 C, which implies that the buffer has an effective pH range between 7.1 and 9.0.

UNII KEGG ChEBI ChEMBL RTECS number ATC code

023C2WHX2V D00396 CHEBI:9754 CHEMBL1200391 TY2900000 B05BB03 (http://www.whocc.no /atc_ddd_index/?code=B05BB03) ,B05XX02

Buffer details
The pKa declines approximately 0.03 units per degree Celsius rise in temperature. Silver-containing single-junction pH electrodes (e.g., silver chloride electrode) are incompatible with Tris (Ag-tris precipitation clogs the junction). Doublejunction electrodes are resistant to this problem, and non-silver containing electrodes are immune. When making buffer solutions by neutralizing TrisHCl requires attention to the attendant changes in ionic strength.
[2][3]

Jmol-3D images

Image 1 (http://chemapps.stolaf.edu /jmol/jmol.php?model=OCC%28N %29%28CO%29CO) SMILES InChI Properties

Molecular formula

C4H11NO3

Buffer inhibition
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Tris - Wikipedia, the free encyclopedia

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Tris inhibits a number of enzymes,[4][5] and therefore it should be used with care when studying proteins.

Molar mass 121.14 g mol1 Appearance White crystalline powder Density 1.328g/cm3 >175-176 C (448-449 K)

Preparation
Tris is prepared industrially in two steps from nitromethane via the intermediate (HOCH2)3CNO2. Reduction of the latter gives tris(hydroxymethyl)aminomethane.
[6]

Melting point Boiling point

219 C, 492 K, 426 F

Solubility in ~50 g/100 mL (25 C)

Uses
The useful buffer range for tris (7-9) coincides with the physiological pH typical of most living organisms. This, and its low cost, make tris one of the most common buffers in the biology/biochemistry laboratory. Tris is also used as a primary standard to standardize acid solutions for chemical analysis.

water Acidity (pKa) Hazards MSDS R-phrases S-phrases External MSDS (http://hazard.com /msds/mf/baker/baker/files/t7111.htm) R36 R37 R38 S26 S36 Irritant 8.07

Medical
Tris (usually known as THAM in this context) is used as alternative to sodium bicarbonate in the treatment of metabolic acidosis.[7]

Main hazards NFPA 704

See also
MOPS HEPES MES Common buffer compounds used in biology

Flash point Non-flammable (verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references

References
1. ^ Gomori, G., Preparation of Buffers for Use in Enzyme Studies (http://2008.igem.org/wiki/images /8/84/Protein_Buffers.pdf) . Methods Enzymology., 1, 138-146 (1955). 2. ^ El-Harakany, A.A.; Abdel Halima, F.M. and Barakat, A.O. (1984). "Dissociation constants and related thermodynamic quantities of the protonated acid form of tris-(hydroxymethyl)-aminomethane in mixtures of 2-methoxyethanol and water at different temperatures". J. Electroanal. Chem. 162 (12): 285305. doi:10.1016/S0022-0728(84)80171-0 (http://dx.doi.org /10.1016%2FS0022-0728%2884%2980171-0) . 3. ^ Vega, C.A.; Butler, R.A. et al. (1985). "Thermodynamics of the Dissociation of Protonated Tris(hydroxymethy1)aminomethane in 25 and 50 wt % 2-Propanol from 5 to 45 C". J. Chem. Eng. Data 30 (4): 376379. doi:10.1021/je00042a003 (http://dx.doi.org/10.1021%2Fje00042a003) . 4. ^ Desmarais, WT; et al. (2002). "The 1.20 resolution crystal structure of the aminopeptidase from Aeromonas proteolytica complexed with Tris: A tale of buffer inhibition". Structure 10 (8): 10631072. doi:10.1016/S0969-2126(02)00810-9 (http://dx.doi.org /10.1016%2FS0969-2126%2802%2900810-9) . PMID 12176384 (//www.ncbi.nlm.nih.gov/pubmed /12176384) . 5. ^ Ghalanbor, Z; et al. (2008). "Binding of Tris to Bacillus licheniformis alpha-amylase can affect its

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starch hydrolysis activity". Protein Peptide Lett. 15 (2): 212214. doi:10.2174/092986608783489616 (http://dx.doi.org/10.2174%2F092986608783489616) . PMID 18289113 (//www.ncbi.nlm.nih.gov/pubmed /18289113) . 6. ^ Markofsky, Sheldon B. (2000). Nitro Compounds, Aliphatic. doi:10.1002/14356007.a17_401

(http://dx.doi.org/10.1002%2F14356007.a17_401) . 7. ^ Kallet, RH; Jasmer RM, Luce JM et al. (2000). "The treatment of acidosis in acute lung injury with tris-hydroxymethyl aminomethane (THAM)". American Journal of Respiratory and Critical Care Medicine 161 (4): 11491153. PMID 10764304 (//www.ncbi.nlm.nih.gov/pubmed/10764304) .

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