1-Hydroxy-7-azabenzotriazole

Last updated
1-Hydroxy-7-azabenzotriazole
1-hydroxy-7-aza-benzotriazole.svg
1-Hydroxy-7-azabenzotriazole molecule spacefill from xtal.png
Names
Preferred IUPAC name
3H-[1,2,3]Triazolo[4,5-b]pyridin-3-ol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.122.938 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H Yes check.svgY
    Key: FPIRBHDGWMWJEP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H
    Key: FPIRBHDGWMWJEP-UHFFFAOYAJ
  • n1cccc2nnn(O)c12
Properties
C5H4N4O
Molar mass 136.114 g·mol−1
Density 0.973 g/mL
Melting point 213-216°C
Hazards
GHS labelling: [1]
GHS-pictogram-explos.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H204, H301, H302, H315, H318, H319, H335
P210, P240, P250, P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P370+P380, P372, P373, P374, P401, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

1-Hydroxy-7-azabenzotriazole (HOAt) is a triazole used as a peptide coupling reagent. [2] It suppresses racemization that can otherwise occur during the reaction. [3]

HOAt has a melting point between 213 and 216 degrees Celsius. [4] As a liquid, it is transparent and without any color.

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<span class="mw-page-title-main">Peptide synthesis</span> Production of peptides

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis in living organisms occurs in the opposite direction.

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<i>N</i>-Hydroxysuccinimide Chemical compound

N-Hydroxysuccinimide (NHS) is an organic compound with the formula (CH2CO)2NOH. It is a white solid that is used as a reagent for preparing active esters in peptide synthesis. It can be synthesized by heating succinic anhydride with hydroxylamine or hydroxylamine hydrochloride.

The molecular formula C5H4N4O (molar mass: 136.11 g/mol, exact mass: 136.0385 u) may refer to:

<span class="mw-page-title-main">HATU</span> Chemical compound

HATU is a reagent used in peptide coupling chemistry to generate an active ester from a carboxylic acid. HATU is used along with Hünig's base, or triethylamine to form amide bonds. Typically DMF is used as solvent, although other polar aprotic solvents can also be used.

The Steglich esterification is a variation of an esterification with dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. The reaction was first described by Wolfgang Steglich in 1978. It is an adaptation of an older method for the formation of amides by means of DCC (dicyclohexylcarbodiimide) and 1-hydroxybenzotriazole (HOBT).

<span class="mw-page-title-main">HBTU</span> Chemical compound

HBTU is a coupling reagent used in solid phase peptide synthesis. It was introduced in 1978 and shows resistance against racemization. It is used because of its mild activating properties.

<span class="mw-page-title-main">PyAOP reagent</span> Chemical compound

PyAOP is a coupling reagent used in solid phase peptide synthesis. It is a derivative of the HOAt family of coupling reagents. It is preferred over HATU, because it does not side react at the N-terminus of the peptide. Compared to the HOBt derivates, PyAOP are more reactive due to the additional nitrogen.

<span class="mw-page-title-main">Ethyl cyanohydroxyiminoacetate</span> Chemical compound

Ethyl cyanohydroxyiminoacetate (oxyma) is the oxime of ethyl cyanoacetate and finds use as an additive for carbodiimides, such as dicyclohexylcarbodiimide (DCC) in peptide synthesis. It acts as a neutralizing reagent for the basicity or nucleophilicity of the DCC due to its pronounced acidity and suppresses base catalyzed side reactions, in particular racemization.

HOAt is 1-Hydroxy-7-azabenzotriazole, a reagent used in organic chemistry.

<span class="mw-page-title-main">Thiocarbonyldiimidazole</span> Chemical compound

1,1'-Thiocarbonyldiimidazole (TCDI) is a thiourea containing two imidazole rings. It is the sulfur analog of the peptide coupling reagent carbonyldiimidazole (CDI).

References

  1. GHS: Sigma Aldrich 445452
  2. Carpino, Louis A (1993). "1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive". Journal of the American Chemical Society. 115 (10): 4397–4398. doi:10.1021/ja00063a082.
  3. Valeur, Eric; Bradley, Mark (2009). "Amide bond formation: beyond the myth of coupling reagents". Chemical Society Reviews. 38 (2): 606–631. doi:10.1039/b701677h. PMID   19169468.
  4. "HOAt". Chemical Book. Retrieved January 30, 2019.