1-hydroxy-7-azabenzotriazole

Structural formula
General
Surname	1-hydroxy-7-azabenzotriazole
other names	3-hydroxytriazolo [4,5- b ] pyridine; 3 H - [1,2,3] -triazolo [4,5- b ] pyridin-3-ol; HOAt;
Molecular formula	C 5 H 4 N 4 O
Brief description	light yellow solid
External identifiers / databases
EC number	609-760-3
ECHA InfoCard	100.122.938
PubChem	181649
Wikidata	Q4545784
properties
Molar mass	136.11 g mol −1
Physical state	firmly
Melting point	213–216 ° C (decomposition)
safety instructions
H and P phrases	H: 204-301-315-318-335
	P: 261-280-301 + 310-305 + 351 + 338-370 + 380-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1-Hydroxy-7-azabenzotriazole (HOAt) is a triazole that is used in organic chemistry and biochemistry as an additive for peptide synthesis and generally for the coupling of amino acids . HOAt reduces the racemization . Alternatively, hydroxybenzotriazole (HOBT), HATU , HBTU , TBTU , N -hydroxysuccinimide or ethyl 2-cyano-2- (hydroxyimino) acetate (Oxyma) are used. HOAt is also used for cross-linking of proteins used.

Individual evidence

↑ ^a ^b ^c ^d ^e Data sheet 1-Hydroxy-7-azabenzotriazole, 98% from Sigma-Aldrich , accessed on August 1, 2014 ( PDF ).
↑ Holger Wenschuh, Michael Beyermann, Hanka Haber, Joachim K. Seydel, Eberhard Krause, Michael Bienert, Louis A. Carpino, Ayman El-Faham, Fernando Albericio: Stepwise Automated Solid Phase Synthesis of Naturally Occurring Peptaibols Using FMOC Amino Acid Fluorides. In: The Journal of Organic Chemistry. 60, 1995, pp. 405-410, doi : 10.1021 / jo00107a020 .
↑ GB Fields: Introduction to peptide synthesis. In: Current protocols in molecular biology / edited by Frederick M. Ausubel ... [et al.]. Chapter 11 August 2002, S. Unit 11.15, doi : 10.1002 / 0471142727.mb1115s59 . PMID 18265296 .

↑ Louis A Carpino, Ayman El-Faham: The diisopropylcarbodiimide / 1-hydroxy-7-azabenzotriazole system: Segment coupling and stepwise peptide assembly. In: Tetrahedron. 55, 1999, pp. 6813-6830, doi : 10.1016 / S0040-4020 (99) 00344-0 .

↑ J. Klose, A. El-Faham, P. Henklein, LA Carpino, M. Bienert: Addition of HOAt dramatically improves the effectiveness of pentafluorophenyl-based coupling reagents. In: Tetrahedron Letters . 40, 1999, p. 2045, doi : 10.1016 / S0040-4039 (99) 00089-1 .

↑ R. Subirós-Funosas, R. Prohens, R. Barba, A. El-Faham, F. Albericio: Oxyma: an efficient additive for peptide synthesis to replace the benzotriazoles-based HOBt and HOAt with a lower risk of explosion. In: Chemistry. Volume 15, number 37, September 2009, pp. 9394-9403, doi : 10.1002 / chem.200900614 . PMID 19575348 .

↑ C. Bich, S. Maedler, K. Chiesa, F. DeGiacomo, N. Bogliotti, R. Zenobi : Reactivity and applications of new amine reactive cross-linkers for mass spectrometric detection of protein-protein complexes. In: Analytical chemistry. Volume 82, Number 1, January 2010, pp. 172-179, doi : 10.1021 / ac901651r . PMID 19994840 .

[Sigma-1] Data sheet 1-Hydroxy-7-azabenzotriazole, 98% from Sigma-Aldrich , accessed on August 1, 2014 ( PDF ).

[DOI10.1021/jo00107a020-2] Holger Wenschuh, Michael Beyermann, Hanka Haber, Joachim K. Seydel, Eberhard Krause, Michael Bienert, Louis A. Carpino, Ayman El-Faham, Fernando Albericio: Stepwise Automated Solid Phase Synthesis of Naturally Occurring Peptaibols Using FMOC Amino Acid Fluorides. In: The Journal of Organic Chemistry. 60, 1995, pp. 405-410, doi : 10.1021 / jo00107a020 .

[3] GB Fields: Introduction to peptide synthesis. In: Current protocols in molecular biology / edited by Frederick M. Ausubel ... [et al.]. Chapter 11 August 2002, S. Unit 11.15, doi : 10.1002 / 0471142727.mb1115s59 . PMID 18265296 .

[DOI10.1016/S0040-4020(99)00344-0-4] Louis A Carpino, Ayman El-Faham: The diisopropylcarbodiimide / 1-hydroxy-7-azabenzotriazole system: Segment coupling and stepwise peptide assembly. In: Tetrahedron. 55, 1999, pp. 6813-6830, doi : 10.1016 / S0040-4020 (99) 00344-0 .

[Klose-5] J. Klose, A. El-Faham, P. Henklein, LA Carpino, M. Bienert: Addition of HOAt dramatically improves the effectiveness of pentafluorophenyl-based coupling reagents. In: Tetrahedron Letters . 40, 1999, p. 2045, doi : 10.1016 / S0040-4039 (99) 00089-1 .

[6] R. Subirós-Funosas, R. Prohens, R. Barba, A. El-Faham, F. Albericio: Oxyma: an efficient additive for peptide synthesis to replace the benzotriazoles-based HOBt and HOAt with a lower risk of explosion. In: Chemistry. Volume 15, number 37, September 2009, pp. 9394-9403, doi : 10.1002 / chem.200900614 . PMID 19575348 .

[7] C. Bich, S. Maedler, K. Chiesa, F. DeGiacomo, N. Bogliotti, R. Zenobi : Reactivity and applications of new amine reactive cross-linkers for mass spectrometric detection of protein-protein complexes. In: Analytical chemistry. Volume 82, Number 1, January 2010, pp. 172-179, doi : 10.1021 / ac901651r . PMID 19994840 .