WordNet

a methyl with the hydrogen atom replaced by an amino radical
a methyl with hydroxide replacing the hydrogen atoms

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/08/23 02:35:58」(JST)

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Tris or Tris(hydroxymethyl)aminomethane or THAM is an organic compound 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 contains a primary amine and thus undergoes the reactions associated with typical amines, e.g. condensations with aldehydes.

Buffering features

Tris has a pK_a of 8.07 at 25 °C, which implies that the buffer has an effective pH range between 7.5 and 9.0.

Buffer details

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

Buffer inhibition

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

Preparation

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

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.

Tris is used to increase membrane permeability of cell membranes.^[7]

Medical

Tris (usually known as THAM in this context) is used as alternative to sodium bicarbonate in the treatment of metabolic acidosis.^[8]^[9]

References

^ Gomori, G., Preparation of Buffers for Use in Enzyme Studies. Methods Enzymology., 1, 138-146 (1955).
^ 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 (1–2): 285–305. doi:10.1016/S0022-0728(84)80171-0.
^ 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): 376–379. doi:10.1021/je00042a003.
^ Desmarais, WT et al. (2002). "The 1.20 Å resolution crystal structure of the aminopeptidase from Aeromonas proteolytica complexed with Tris: A tale of buffer inhibition". Structure 10 (8): 1063–1072. doi:10.1016/S0969-2126(02)00810-9. PMID 12176384.
^ Ghalanbor, Z et al. (2008). "Binding of Tris to Bacillus licheniformis alpha-amylase can affect its starch hydrolysis activity". Protein Peptide Lett. 15 (2): 212–214. doi:10.2174/092986608783489616. PMID 18289113.
^ Markofsky, Sheldon B. (2000). "Nitro Compounds, Aliphatic". doi:10.1002/14356007.a17_401.
^ Irvin, R.T.; MacAlister, T.J.; Costerton, J.W. (1981). "Tris(hydroxymethyl)aminomethane Buffer Modification of Escherichia coli Outer Membrane Permeability". J. Bacteriol 145 (3): 1397–1403.
^ 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): 1149–1153. doi:10.1164/ajrccm.161.4.9906031. PMID 10764304.
^ Hoste, EA; Colpaert, K; Vanholder, RC; Lameire, NH; De Waele, JJ; Blot, SI; Colardyn, FA (2005). "Sodium bicarbonate versus THAM in ICU patients with mild metabolic acidosis.". Journal of nephrology 18 (3): 303–7. PMID 16013019.

UpToDate Contents

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English Journal

Differential influence of 7 cations on 16 non-competitive NMDA receptor blockers.

Berger ML1, Rebernik P1.
Bioorganic & medicinal chemistry letters.Bioorg Med Chem Lett.2015 Oct 1;25(19):4131-5. doi: 10.1016/j.bmcl.2015.08.017. Epub 2015 Aug 8.
The specific binding of the NMDA receptor (NR) channel ligand [(3)H]MK-801 to rat brain membranes is sensitive to positively charged buffer ingredients as to tris(hydroxymethyl)aminomethane (Tris), to Na(+), or to protons. Here we demonstrate that 16 non-competitive NR antagonists, including 5 long-
PMID 26296478

Synthesis and characterization of [Zn(acetate)2(amine)x] compounds (x = 1 or 2) and their use as precursors to ZnO.

Hyslop JS1, Boydstun AR1, Fereday TR1, Rusch JR1, Strunk JL1, Wall CT1, Pena CC1, McKibben NL1, Harris JD1, Thurber A2, Punnoose A2, Brotherton J3, Walker P3, Lowe L3, Rapp B3, Purnell S3, Knowlton WB3, Hubbard SM4, Frost BJ5.
Materials science in semiconductor processing.Mater Sci Semicond Process.2015 Oct;38:278-289.
As an obvious candidate for a p-type dopant in ZnO, nitrogen remains elusive in this role. Nitrogen containing precursors are a potential means to incorporate nitrogen during MOCVD growth. One class of nitrogen-containing precursors are zinc acetate amines, yet, they have received little attention.
PMID 26085801

Binding and stabilisation effects of glycodendritic compounds with peanut agglutinin.

Sleiman MH1, Csonka R1, Arbez-Gindre C1, Heropoulos GA1, Calogeropoulou T1, Signorelli M2, Schiraldi A2, Steele BR1, Fessas D3, Micha-Screttas M4.
International journal of biological macromolecules.Int J Biol Macromol.2015 Sep;80:692-701. doi: 10.1016/j.ijbiomac.2015.07.036. Epub 2015 Jul 20.
A number of new polyhydroxy-dendritic structures have been constructed from a few basic modules. The cores were derived from N-tert(butyloxycarbonyl)tris[(propargyloxy)methyl]aminomethane, N,N'-bis-1,3-(tris-(propargyloxymethyl)methyl)-5-(hydroxymethyl)isophthalamide, and N,N',N″-tris-1,3,5-(tris-
PMID 26206739

Japanese Journal

Effects of Sugar and Buffer Types, and pH on Formation of Maillard Pigments in the Lysine Model System

Food Science and Technology Research 21(6), 813-819, 2015
NAID 130005122048

Relationship between Aggregated Structures and Dispersibility of Layered Double Hydroxide Nanoparticles ca. 10 nm in Size and Their Application to Ultrafast Removal of Aqueous Anionic Dye

Bulletin of the Chemical Society of Japan 88(12), 1765-1772, 2015
NAID 130005113814

Relationship between Aggregated Structures and Dispersibility of Layered Double Hydroxide Nanoparticles ca. 10 nm in Size and Their Application to Ultrafast Removal of Aqueous Anionic Dye

Bulletin of the Chemical Society of Japan advpub(0), 2015
NAID 130005100907

Related Pictures

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関連記事	「Tris」「aminomethane」「tri」「hydroxymethyl」

「Tris」

Tris
Names
	IUPAC name 2-Amino-2-hydroxymethyl-propane-1,3-diol
	Other names TRIS, Tris, Tris base, Tris buffer, Trizma, Trisamine, THAM, Tromethamine, Trometamol, Tromethane, Trisaminol
Identifiers
CAS Registry Number	77-86-1
ATC code	B05BB03; B05XX02
ChEBI	CHEBI:9754
ChEMBL	ChEMBL1200391
ChemSpider	6257
	InChI InChI=1S/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2 ; Key: LENZDBCJOHFCAS-UHFFFAOYSA-N ; InChI=1/C4H11NO3/c5-4(1-6,2-7)3-8/h6-8H,1-3,5H2; Key: LENZDBCJOHFCAS-UHFFFAOYAN ;
IUPHAR/BPS	7328
Jmol-3D images	Image
KEGG	D00396
PubChem	6503
RTECS number	TY2900000
	SMILES OCC(N)(CO)CO ;
UNII	023C2WHX2V
Properties
Chemical formula	C4H11NO3
Molar mass	121.14 g·mol−1
Appearance	White crystalline powder
Density	1.328g/cm3
Melting point	>175-176 °C (448-449 K)
Boiling point	219 °C (426 °F; 492 K)
Solubility in water	~50 g/100 mL (25 °C)
Acidity (pKa)	8.07
Hazards
Main hazards	Irritant
Safety data sheet	External MSDS
R-phrases	R36 R37 R38
S-phrases	S26 S36
NFPA 704	2
Flash point	Non-flammable
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references