1-Hydroxy-7-azabenzotriazole (HOAt) is a chemical compound that plays a crucial role in organic synthesis, particularly in peptide synthesis.
**Structure and Properties:**
HOAt is a heterocyclic compound with a 7-membered ring containing a nitrogen atom and a hydroxyl group attached to the first carbon atom. Its molecular formula is C5H4N2O2.
**Importance in Research:**
HOAt is a highly effective additive used in peptide synthesis, specifically in **solid-phase peptide synthesis (SPPS)**. Here's why it's important:
* **Activation of Amino Acids:** HOAt, in combination with a coupling reagent like HBTU (O-benzotriazole-N,N,N',N'-tetramethyluronium hexafluorophosphate), helps activate the carboxyl group of amino acids. This activation facilitates the formation of a reactive species, allowing the amino acid to efficiently couple with the growing peptide chain.
* **Improved Coupling Efficiency:** HOAt significantly enhances the efficiency of peptide bond formation, leading to higher yields and reduced side reactions. It effectively minimizes racemization, a common problem in peptide synthesis that can lead to unwanted isomers.
* **Minimization of Racemization:** HOAt contributes to reducing racemization by promoting the formation of a more stable intermediate during the coupling reaction. This stability prevents the formation of undesired enantiomers.
* **Versatile Applications:** HOAt's use extends beyond SPPS. It finds applications in various organic synthesis reactions, such as the synthesis of esters, amides, and other functional groups.
**Research Applications:**
HOAt's importance lies in its contribution to research involving peptides and proteins:
* **Drug Discovery:** HOAt is crucial in the synthesis of peptides and protein fragments used in drug discovery and development. It allows researchers to create complex and biologically active molecules for therapeutic applications.
* **Biochemistry and Molecular Biology:** HOAt aids in the synthesis of peptides and proteins used in biochemical and molecular biological studies. This allows for the investigation of protein structure, function, and interactions.
* **Materials Science:** HOAt contributes to the synthesis of peptides and proteins used in materials science, particularly in the development of biomaterials and nanomaterials.
In conclusion, 1-hydroxy-7-azabenzotriazole (HOAt) is a valuable reagent in organic synthesis, particularly in peptide synthesis. Its ability to enhance coupling efficiency, minimize racemization, and facilitate the formation of peptide bonds makes it an essential tool in drug discovery, biochemistry, molecular biology, and materials science research.
1-hydroxy-7-azabenzotriazole: structure in first source
ID Source | ID |
---|---|
PubMed CID | 181649 |
SCHEMBL ID | 563818 |
SCHEMBL ID | 5393 |
MeSH ID | M0400072 |
Synonym |
---|
inchi=1/c5h4n4o/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10 |
1-hydroxy-7-azabenzotriazole |
STK503884 |
3h-[1,2,3]triazolo[4,5-b]pyridin-3-ol |
AKOS000265235 |
3h-1,2,3-triazolo[4,5-b]pyridin-3-ol |
3-hydroxytriazolo[4,5-b]pyridine |
3h-1,2,3-triazolo(4,5-b)pyridine, 3-hydroxy- |
unii-tx8xyh09h0 |
tx8xyh09h0 , |
hoat |
39968-33-7 |
3-oxidanyl-[1,2,3]triazolo[4,5-b]pyridine |
A824827 |
T1673 |
7-aza-1-hydroxybenzotriazole |
hoat [1-hydroxy-7-azabenzotriazole] |
BP-12721 |
FT-0600904 |
AM20061760 |
3h-1,2,3-triazolo[4,5-b]pyridine, 3-hydroxy- |
3h-1,2,3-triazolo(4,5-b)pyridine-3-ol |
1-hydroxy-1h-v-triazolo(4,5-b)pyridine |
3h-(1,2,3)triazolo(4,5-b)pyridin-3-ol |
1-hydroxy-7-azabenzotriazole [mi] |
1-hydroxyl-7-azabenzotriazole |
(1,2,3)triazolo(4,5-b)pyridin-3-ol |
SCHEMBL563818 |
hoat 1-hydroxy-7-azabenzotriazole |
SCHEMBL5393 |
3h-[1,2,3]-triazolo[4,5-b]pyridin-3-ol |
1-hydroxy-7-azabenzotriazol |
1-hydroxy-7 azabenzotriazole |
1-hydroxy-7-azabenzo-triazole |
1-hydroxy-7azabenzotriazole |
[1,2,3]triazolo[4,5-b]pyridin-3-ol |
FPIRBHDGWMWJEP-UHFFFAOYSA-N |
1-hydroxy-7-aza-benzotriazole |
1-hydroxy-7-aza-1h-1,2,3-benzotriazole |
3h-1,2,3-triazolo[4,5-b]pyridine-3-ol |
1-hydroxy-7-azabenztriazole |
3-hydroxy-3h-1,2,3-triazolo[4,5-b]pyridine |
W-202647 |
AC-24873 |
DTXSID0075239 |
Z1203162550 |
CS-W019594 |
BBL104414 |
BCP25461 |
Q4545784 |
mfcd00210053 |
AS-11821 |
57115-46-5 |
1-hydroxy-t-axabenzotrazole |
hoat form ii |
hoat form i |
1-hydroxy-7-azabenzotriazole; 3h-[1,2,3]-triazolo[4,5-b]pyridin-3-ol |
SB40481 |
EN300-194281 |
hoat solution |
1-hydroxy-7-azabenzotriazole solution |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 10 (71.43) | 29.6817 |
2010's | 4 (28.57) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (27.42) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 14 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |