HOAtcoupling activator for racemization-free coupling in peptide synthesis CAS# 39968-33-7 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 39968-33-7 | SDF | Download SDF |
PubChem ID | 181649 | Appearance | Powder |
Formula | C5H4N4O | M.Wt | 136.11 |
Type of Compound | N/A | Storage | Desiccate at -20°C |
Solubility | >6.8mg/mL in DMSO | ||
Chemical Name | 3-hydroxytriazolo[4,5-b]pyridine | ||
SMILES | C1=CC2=C(N=C1)N(N=N2)O | ||
Standard InChIKey | FPIRBHDGWMWJEP-UHFFFAOYSA-N | ||
Standard InChI | InChI=1S/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
HOAt Dilution Calculator
HOAt Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 7.347 mL | 36.735 mL | 73.47 mL | 146.94 mL | 183.675 mL |
5 mM | 1.4694 mL | 7.347 mL | 14.694 mL | 29.388 mL | 36.735 mL |
10 mM | 0.7347 mL | 3.6735 mL | 7.347 mL | 14.694 mL | 18.3675 mL |
50 mM | 0.1469 mL | 0.7347 mL | 1.4694 mL | 2.9388 mL | 3.6735 mL |
100 mM | 0.0735 mL | 0.3673 mL | 0.7347 mL | 1.4694 mL | 1.8367 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
A coupling activator for racemization-free coupling in peptide synthesis; An additive for peptide segment coupling in in reducing the extent of configurational loss at the reactive carboxylic acid residue. Carpino L A etc. works demonstrated that the DIC/HOAt system is more effective in preserving configuration for peptide segment coupling than the analogous DIC/HOBt system
in DMF and DCM. [1]
Reference:
Carpino L A, El-Faham A. The diisopropylcarbodiimide/1-hydroxy-7-azabenzotriazole system: segment coupling and stepwise peptide assembly[J]. Tetrahedron, 1999, 55(22): 6813-6830.
- Victoxinine
Catalog No.:BCN6745
CAS No.:39965-06-5
- LY 78335
Catalog No.:BCC6109
CAS No.:39959-66-5
- Norglaucine hydrochloride
Catalog No.:BCN6568
CAS No.:39945-41-0
- 2'-Deoxycytidine hydrochloride
Catalog No.:BCC5434
CAS No.:3992-42-5
- 29-Hydroxyfriedelan-3-one
Catalog No.:BCN5453
CAS No.:39903-21-4
- H-D-Phe(4-OMe)-OH
Catalog No.:BCC2633
CAS No.:39878-65-4
- PHA-680632
Catalog No.:BCC2178
CAS No.:398493-79-3
- JNJ 5207852 dihydrochloride
Catalog No.:BCC6101
CAS No.:398473-34-2
- 19-Hydroxybufalin
Catalog No.:BCN8237
CAS No.:39844-86-5
- Methyllinderone
Catalog No.:BCN5452
CAS No.:3984-73-4
- Amikacin disulfate
Catalog No.:BCC4622
CAS No.:39831-55-5
- H-Ala-OiPr.HCl
Catalog No.:BCC3193
CAS No.:39825-33-7
- Delta-9-Tetrahydrocannabivarinic acid
Catalog No.:BCN7967
CAS No.:39986-26-0
- p-Hydroxy-5,6-dehydrokawain
Catalog No.:BCN3597
CAS No.:39986-86-2
- Laricitrin 3-O-glucoside
Catalog No.:BCN8149
CAS No.:39986-90-8
- H-Thr-OMe.HCl
Catalog No.:BCC3104
CAS No.:39994-75-7
- 24, 25-Dihydroxy VD3
Catalog No.:BCC1303
CAS No.:40013-87-4
- Syringetin-3-O-glucoside
Catalog No.:BCN2610
CAS No.:40039-49-4
- SU 3327
Catalog No.:BCC7725
CAS No.:40045-50-9
- N6-Benzoyladenine
Catalog No.:BCC9075
CAS No.:4005-49-6
- 20-Hydroxyganoderic acid G
Catalog No.:BCN8231
CAS No.:400604-12-8
- Ceftaroline fosamil
Catalog No.:BCC5266
CAS No.:400827-46-5
- H-Arg-pNA.2HCl
Catalog No.:BCC2858
CAS No.:40127-11-5
- Erucifoline
Catalog No.:BCN2081
CAS No.:40158-95-0
Peptide bond-forming reagents HOAt and HATU are not mutagenic in the bacterial reverse mutation test.[Pubmed:26840011]
Environ Mol Mutagen. 2016 Apr;57(3):236-40.
The peptide bond-forming reagents 1-hydroxy-7-azabenzotriazole (HOAt, CAS 39968-33-7) and O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU, CAS 148893-10-1) either have structural alerts, unclassified features or are considered out of domain when evaluated for potential mutagenicity with in silico programs DEREK and CaseUltra. Since they are commonly used reagents in pharmaceutical drug syntheses, they may become drug substance or drug product impurities and would need to be either controlled to appropriately safe levels or tested for mutagenicity. Both reagents were tested in the bacterial reverse mutation (Ames) test at Covance, under GLP conditions, following the OECD test guideline and ICH S2(R1) recommendations and found to be negative. Our data show that HOAt and HATU-common pharmaceutical synthesis reagents-are not mutagenic, and can be treated as ordinary drug impurities.
Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.[Pubmed:19575348]
Chemistry. 2009 Sep 21;15(37):9394-403.
Oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate] has been tested as an additive for use in the carbodiimide approach for formation of peptide bonds. Its performance in relation to those of HOBt and HOAt, which have recently been reported to exhibit explosive properties, is reported. Oxyma displayed a remarkable capacity to inhibit racemization, together with impressive coupling efficiency in both automated and manual synthesis, superior to those of HOBt and at least comparable to those of HOAt, and surpassing the latter coupling agent in the more demanding peptide models. Stability assays showed that there was no risk of capping the resin under standard coupling conditions. Finally, calorimetry assays (DSC and ARC) showed decomposition profiles for benzotriazole-based additives that were consistent with their reported explosivities and suggested a lower risk of explosion in the case of Oxyma.
Reactions of monoaryl-substituted methylenecyclobutanes and methylenecyclopropanes with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu).[Pubmed:19222218]
J Org Chem. 2009 Mar 20;74(6):2516-20.
Monoaryl-substituted methylenecyclobutanes (MCBs) and methylenecyclopropanes (MCPs) react with 1-hydroxybenzotriazole (HOBt), 1-hydroxy-7-azabenzotriazole (HOAt), and 1-hydroxysuccinimide (HOSu) smoothly to produce the corresponding cyclobutylmethanone and cyclopropylmethanone derivatives 2, 4, and 5 via a cascade epoxidation and nucleophilic addition process or the corresponding epoxides 6 in moderate to good yields under mild conditions. A plausible mechanism has been proposed on the basis of the control experiments and the isolation of the reaction intermediates.