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Application Area

HODHBt

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

HOOBt is a STAT5-SUMO protein-protein interaction inhibitor that suppresses SUMOylation of phosphorylated STAT5.

Category

Peptide Synthesis Reagents

Catalog number

BAT-008117

CAS number

28230-32-2

Molecular Formula

C23H27N3O5

Molecular Weight

425.5

Specification
Reference Reading

IUPAC Name

3-hydroxy-1,2,3-benzotriazin-4-one

Synonyms

28230-32-2;3-Hydroxy-1,2,3-benzotriazin-4(3H)-one;HOOBT;HODHBT;3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine;3-hydroxy-1,2,3-benzotriazin-4-one;3-Hydroxy-1,2,3-ben zotriazin-4(3H)-one;1,2,3-Benzotriazin-4(3H)-one, 3-hydroxy-;Z5000NB5EL;3-HYDROXYBENZO[D][1,2,3]TRIAZIN-4(3H)-ONE;NSC-279266;3-HYDROXY-3,4-DIHYDRO-1,2,3-BENZOTRIAZIN-4-ONE;3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine;EINECS 248-916-1;NSC279266;DHOBT;NSC 279266;SCHEMBL2954;UNII-Z5000NB5EL;3-Hydroxy-4-ketobenzotriazine;SCHEMBL7446559;SCHEMBL8853999;HJBLUNHMOKFZQX-UHFFFAOYSA-;3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (DHBT);DTXSID10182487;HY-Y0493;AKOS003388537;3-hydroxy-1,2,3-benzotriazine-4-one;AC-7860;AM83837;GS-3340;3-hydroxy1,2,3-benzotriazin-4(3H)-one;3-hydroxy 1,2,3-benzotriazin-4(3H)-one;3-hydroxy,1,2,3-benzotriazin-4(3H)-one;3-Hydroxy-1,2,3-benzotruazin-4(3H)-one;3-hydroxy-3H-[1,2,3]benzotriazin-4-one;3-hydroxy-1,2,3-benzotriazin-4-(3H)-one;3-hydroxy-1,2,3-benzotriazine-4(3h)-one;CS-0015278;D2039;NS00049958;3-Hydroxy-1,2,3-benzotriazin-4(3H)-one #;O11014;3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazin;3-Hydroxy-1,2,3-benzotriazin-4(3H)-one, 98%;A819380;3-Hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine;4-oxo-3,4-dihydro-3-hydroxy-1,2,3-benzotriazine;W-107062;3-HYDROXY-3H-BENZO[D][1,2,3]TRIAZIN-4-ONE;InChI=1/C7H5N3O2/c11-7-5-3-1-2-4-6(5)8-9-10(7)12/h1-4,12H;3-Hydroxy-1,2,3-benzotriazin-4(3H)-one; 3 ,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine; 3-Hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine;

Appearance

Solid

Purity

98% (HPLC)

Density

1.041 g/cm3 (Predicted)

Melting Point

184-189 °C

Boiling Point

290.1 °C (Predicted)

Storage

2-8 °C

InChI

InChI=1S/C7H5N3O2/c11-7-5-3-1-2-4-6(5)8-9-10(7)12/h1-4,12H

InChI Key

HJBLUNHMOKFZQX-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)[C@@H]1CN2C(=C3C=CC=C(C3=N2)OCCCOC)C4=CC(=O)C(=CN14)C(=O)O

1. Determination of gibberellins in soybean using tertiary amine labeling and capillary electrophoresis coupled with electrochemiluminescence detection

Shihua Long, Zaibin Hao, Wen Luo, Guimei Zhu, Xia Li, Hao Sun J Chromatogr B Analyt Technol Biomed Life Sci . 2013 Dec 15;941:62-8. doi: 10.1016/j.jchromb.2013.10.004.

A novel sensitive method based on tertiary amine labeling for the analysis of gibberellins (GAs) by capillary electrophoresis (CE) coupled with electrochemiluminescence (ECL) detection was proposed. GA3 was tagged with 2-(2-aminoethyl)-1-methylpyrrolidine (AEMP) using N, N'-dicyclohexylcarbodiimide (DCC) and 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine (HOOBt) as coupling agents in acetonitrile to produce GA3-AEMP-derivative. The GA3-AEMP-derivative was injected into CE by electrokinetic injection and detected by Ru(bpy)3(2+)-based ECL. The parameters affecting derivatization, detection and separation such as concentration of reactants, detection potential, pH and concentration of separation buffer, were investigated in detail. Under optimum conditions, the linear concentration range for GA3 was from 2.0×10(-7) to 1.28×10(-4)M with a correlation coefficient of 0.9997. The detection limit was 8×10(-8)M (S/N=3). The relative standard deviations of migration time, peak intensity and peak area for nine continuous injections of 2.0×10(-5)M GA3-AEMP-derivative were 1.0%, 2.1% and 4.2%, respectively. The developed approach was successfully applied to the determination of total GAs in the stem, leaf and seed of soybean (Glycine max [L.] Merr.) with recoveries in the range from 89.6% to 99.3%.

2. Synthesis and application of acid labile anchor groups for the synthesis of peptide amides by Fmoc-solid-phase peptide synthesis

G Breipohl, J Knolle, W Stüber Int J Pept Protein Res . 1989 Oct;34(4):262-7. doi: 10.1111/j.1399-3011.1989.tb01573.x.

The preparation and application of a new linker for the synthesis of peptide amides using a modified Fmoc-method is described. The new anchor group was developed based on our experience with 4,4'-dimethoxybenzhydryl (Mbh)-protecting group for amides. Lability towards acid treatment was increased dramatically and results in an easy cleavage procedure for the preparation of peptide amides. The synthesis of N-9-fluorenylmethoxycarbonyl- ([5-carboxylatoethyl-2.4-dimethoxyphenyl)- 4'-methoxyphenyl]-methylamin is reported in detail. This linker was coupled to a commercially available aminomethyl polystyrene resin. Peptide synthesis proceeded smoothly using HOOBt esters of Fmoc-amino acids. Release of the peptide amide and final cleavage of the side chain protecting groups was accomplished by treatment with trifluoroacetic acid-dichloromethane mixtures in the presence of scavengers. The synthesis of peptide amides such as LHRH and C-terminal hexapeptide of secretin are given as examples.

3. Synthesis of biantennary complex-type nonasaccharyl asn building blocks for solid-phase glycopeptide synthesis

Mizuki Dohi, Yuya Asahina, Yukishige Ito, Masashi Hagiwara, Yuko Nakahara, Hironobu Hojo, Akiharu Ueki, Keiko Komatsu, Yoshiaki Nakahara J Org Chem . 2011 Jul 1;76(13):5229-39. doi: 10.1021/jo200149d.

The biantennary complex-type N-glycans bearing LacNAc and LacdiNAc as the nonreducing end motif were synthesized in a protected form suitable to use in the Fmoc solid-phase peptide synthesis studies. Two approaches for the nonasaccharide synthesis were examined by taking advantage of the highly β-selective glycosylation with GlcNTCA (N-phenyl)trifluoroacetimidate. An earlier approach, which involved the reaction of the trisaccharide donor (Gal-GlcNTCA-Man) and trisaccharide acceptor (Man-GlcNPhth(2)-N(3)), produced a mixture of nonasaccharide isomers. On the other hand, mannosylation of the trisaccharide acceptor (Man-GlcNPhth(2)-N(3)) stereoselectively afforded the known pentasaccharide (Man(3)-GlcNPhth(2)-N(3)), which was reacted with the disaccharyl glycosyl donor (Gal-GlcNTCA or GalNTCA-GlcNTCA) to produce the desired nonasaccharide as a single stereoisomer. Selective dephthaloylation followed by N-acetylation furnished the GlcNAc(2) functionality. The resulting nonasaccharyl azides were condensed with Fmoc-Asp(OPfp)-OBu(t) or Fmoc-Asp(OPfp)-OPac in the presence of Ph(CH(3))(2)P and HOOBt. Finally, the Zn reduction and cleavage of the tert-butyl ester or Zn reduction alone produced the targeted nonasaccharyl Asn building blocks.