HOAt | CAS:39968-33-7 | coupling activator for ...

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coupling activator for racemization-free coupling in peptide synthesis CAS# 39968-33-7

2D Structure

Quality Control of HOAt

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Chemical Properties of HOAt

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

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Preparing Stock Solutions of HOAt

	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.

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Background on HOAt

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.

References on HOAt

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.

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