A7025-100g | HOBt [2592-95-2] Clinisciences

Hydroxy benzotriazole, abbreviated HOBt, is anorganic compoundthat is a derivative of benzotriazole. HOBt, as a commercial product, is a white crystalline powder contains some water (~11.7% wt as the HOBt monohydrate crystal). It is mainly used to suppress the racemization of single-enantiomerchiral molecules and to improve the efficiency ofpeptide synthesis. Automated peptide synthesisinvolves the condensation of the amino group of protected amino acidswith the activated ester. HOBt can be used to produce activated esters such as N-hydroxysuccinimide ester. These esters are insoluble and react with amines at ambient temperature to give amides [1]. HOBt is also used for the synthesis of amides from carboxylic acidsaside from amino acids. These substrates may not be convertible to theacyl chlorides [2]. For instance amide derivatives of ionophoric antibiotics have been prepared in this way [3].

References:
[1]. Knig W, Geiger R. EineneueMethodezurSynthese von Peptiden: Aktivierung der CarboxylgruppemitDicyclohexylcarbodiimidunterZusatz von 1‐Hydroxy‐benzotriazolen[J]. ChemischeBerichte, 1970, 103(3): 788-798.
[2]. Myers A G, Yang B H, Chen H. Transformation of Pseudoephedrine Amides into Highly Enantiomerically Enriched Aldehydes, Alcohols, and Ketones[J]. Organic Syntheses, 2000: 29-29.
[3]. owicki D, Huczyński A, Ratajczak-Sitarz M, et al. Structural and antimicrobial studies of a new N-phenylamide of monensin A complex with sodium chloride[J]. Journal of Molecular Structure, 2009, 923(1): 53-59.

1. Song Hong, et al. "Development of a Novel Covalently Bonded Conjugate of Caprylic Acid Tripeptide (Isoleucine-Leucine-Aspartic Acid) for Wound-Compatible and Injectable Hydrogel to Accelerate Healing." Biomolecules. 2024 Jan 11;14(1):94. PMID: 38254694
2. Ching-Hsin Huang, Edwin Chang, et al. "Tumor protease-activated theranostic nanoparticles for MRI-guided glioblastoma therapy." Theranostics. 2023 Mar 13;13(6):1745-1758. PMID: 37064879
3. Megan S Michie, Baogang Xu, et al. "Side-chain modification of collagen-targeting peptide prevents dye aggregation for improved molecular imaging of arthritic joints." J Photochem Photobiol A Chem. 2022 Feb 1:424:113624. PMID: 36406204
4. Izabela Maluch, Justyna Grzymska, et al. "Evaluation of the effects of phosphorylation of synthetic peptide substrates on their cleavage by caspase-3 and-7." Biochem J. 2021 Jun 25;478(12):2233-2245. PMID: 34037204
5. Rafiei A, Schriemer DC. "A microtubule crosslinking protocol for integrative structural modeling activities." Anal Biochem. 2019 Sep 6:113416. PMID: 31499019
6. Mengmeng Feng. "Improving the bioavailability of collagen-derived peptides: studies in cell culture models." University of Alberta. 2019.
7. Gilbert T, Alsop RJ, et al. "Nanostructure of Fully Injectable Hydrazone-Thiosuccinimide Interpenetrating Polymer Network Hydrogels Assessed by Small-Angle Neutron Scattering and dSTORM Single-Molecule Fluorescence Microscopy." ACS Appl Mater Interfaces. 2017 Nov 27. PMID: 29131571
8. Johansen ML, Gao Y, et al. "Quantitative Molecular Imaging with a Single Gd-Based Contrast Agent Reveals Specific Tumor Binding and Retention in Vivo." Anal Chem. 2017 Jun 6;89(11):5932-5939. PMID: 28481080
9. Gilbert, Trevor. "Injectable Interpenetrating Network Hydrogels for Biomedical Applications." mcmaster university.2017.
10. Herrmann, Kelsey, et al. "Molecular Imaging of Tumors Using a Quantitative T1 Mapping Technique via Magnetic Resonance Imaging." Diagnostics 5.3 (2015): 318-332.

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Physical Appearance	A solid
Storage	Desiccate at -20°C
M.Wt	135.1
Cas No.	2592-95-2
Formula	C₆H₅N₃O
Solubility	≥22.4 mg/mL in EtOH with ultrasonic; ≥4.09 mg/mL in H2O with ultrasonic; ≥6.76 mg/mL in DMSO
Chemical Name	1-hydroxybenzotriazole
SDF	Download SDF
Canonical SMILES	C1=CC=C2C(=C1)N=NN2O
Shipping Condition	Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips	We do not recommend long-term storage for the solution, please use it up soon.

Description	HOBt is an inhibitor of racemization for peptide synthesis.
Targets	racemization
IC50

Purity = 99.91%

HOBt [2592-95-2]

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