PyBOPpeptide coupling reagent CAS# 128625-52-5 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 128625-52-5 | SDF | Download SDF |
| PubChem ID | 2724700 | Appearance | Powder |
| Formula | C18H28F6N6OP2 | M.Wt | 520.4 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | >52mg/mL in DMSO | ||
| Chemical Name | benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphanium | ||
| SMILES | C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=CC=CC=C5N=N4 | ||
| Standard InChIKey | WGNZRLMOMHJUSP-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C18H28N6OP/c1-2-10-18-17(9-1)19-20-24(18)25-26(21-11-3-4-12-21,22-13-5-6-14-22)23-15-7-8-16-23/h1-2,9-10H,3-8,11-16H2/q+1 | ||
| 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. |
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| 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. |
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| 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. | ||
PyBOP Dilution Calculator
PyBOP Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9216 mL | 9.608 mL | 19.216 mL | 38.432 mL | 48.04 mL |
| 5 mM | 0.3843 mL | 1.9216 mL | 3.8432 mL | 7.6864 mL | 9.608 mL |
| 10 mM | 0.1922 mL | 0.9608 mL | 1.9216 mL | 3.8432 mL | 4.804 mL |
| 50 mM | 0.0384 mL | 0.1922 mL | 0.3843 mL | 0.7686 mL | 0.9608 mL |
| 100 mM | 0.0192 mL | 0.0961 mL | 0.1922 mL | 0.3843 mL | 0.4804 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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IC50: Not available.
PyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate), the analog of BOP where dimethylamino groups are replaced with pyrrolidino, is a peptide coupling reagent used in solid phase peptide synthesis. As the only analog of BOP which shows equivalent properties in peptide bond formation, PyBOP is widely used as a substitute for the BOP, with the aim of avoiding formation of hexamethylphosphoric triamide (HMPA) which is a carcinogenic side product. After being extensively reported with toxicity, HMPA has been recently included in the “Seveso list” of dangerous chemicals. Both in solution and in solid phase peptide synthesis, BOP performs as an excellent peptide coupling reagent. However, formation of HPMA couldn’t be avoided during the manufacture and utilization of BOP. [1]
In vitro: Under the same condition to that of BOP, coupling tests were conducted using PyBOP as coupling reagent. In the DCM molar solution containing N-protected amino acid, compounds were added as follow: coupling reagent, C-protected amino acid hydrochloride and DIEA. An immediate reaction could be then noticed by TLC monitoring, even in the case of hindered amino acids. Moreover, the magnitude of racemization seemed to be 50% lower than that obtained with BOP in the Young’s test, and exhibited superiority in the Anteunis’ test. [1]
In vivo: So far, no in vivo data has been reported.
Clinical trial: So far, no clinical trial has been conducted.
Reference:
[1]Coste J, Le-Nguyen D and Castro B. PyBOP@: A new peptide coupling reagent devoid of toxic by-product. Tetrahedron Lett. 1990 Mar; 31(2): 205-8.
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[Unusual amidation reaction of Asn-containing glycopeptide antibiotics using the coupling reagent PyBOP].[Pubmed:23964514]
Bioorg Khim. 2013 Mar-Apr;39(2):141-50.
The coupling reagent PyBOP is widely used for the synthesis of different peptides and their amides, particularly for carboxamides of glycopeptide antibiotics of vancomycin or teicoplanin groups. The amidation reaction of the peptide core of the glycopeptide antibiotic eremomycin (I) with highly reactive amines in the presence of PyBOP is usually not accompanied by the formation of side products. However, the amidation of I with bulky amines (e.g., decyl amine and adamantyl amine) in the presence of PyBOP and Et3N or di-(i-Pr)2EtN (pH - 8.5) yielded N-unsubstituted carboxamide of eremomycin (Ia) as an admixture. The reaction of (I) or vancomycin (II) with an excess of PyBOP and Et3N (pH - 8.5) without addition of an amine or ammonia gave a mixture of products which contained higher amounts of the corresponding N-unsubstituted carboxamides (-20%). The structures of the samples of Ia and vancomycin amide (IIa) were proved by 1H NMR and ESI MS methods and confirmed by comparing with the authentic samples.
