Page last updated: 2024-12-08

1-hydroxy-7-azabenzotriazole

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

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 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID181649
SCHEMBL ID563818
SCHEMBL ID5393
MeSH IDM0400072

Synonyms (61)

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
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's10 (71.43)29.6817
2010's4 (28.57)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.42

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.

MetricThis Compound (vs All)
Research Demand Index27.42 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]