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12805

Sigma-Aldrich

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

≥97.0% (TLC), for peptide synthesis

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Synonym(s):
PyBOP®
Linear Formula:
C18H28N6OP · PF6
CAS Number:
128625-52-5
Molecular Weight:
520.39
Beilstein:
3584612
MDL number:
MFCD00077411
UNSPSC Code:
12352101
PubChem Substance ID:
329749882
NACRES:
NA.22

grade

purum

Quality Level

200

Assay

≥97.0% (TLC)

form

solid

reaction suitability

reaction type: Coupling Reactions

mp

~150 °C
154-156 °C (dec.) (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

F[P-](F)(F)(F)(F)F.C1CCN(C1)[P+](On2nnc3ccccc23)(N4CCCC4)N5CCCC5

InChI

1S/C18H28N6OP.F6P/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;1-7(2,3,4,5)6/h1-2,9-10H,3-8,11-16H2;/q+1;-1

InChI key

VIAFLMPQBHAMLI-UHFFFAOYSA-N

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General description

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) is an activator of carboxyl group commonly used in peptide synthesis. It also participates in the carboxylic acid esterification. It shows characteristics similar to benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and can be utilized as an alternative to BOP in peptide bond formation.

Application

(Benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP) may be used in the following studies:
  • As coupling reagent in the preparation strategies for peptide-oligonucleotide conjugates.
  • Synthesis of structured pure triacylglycerol (TAG) regioisomers.
  • As coupling reagent in the synthesis of a 3,5-pyrazolidinedione on soluble polyethylene glycol (PEG) polymer support.
  • Synthesis of herceptin- nanoparticles.
Analogue of the BOP coupling reagent which does not form carcinogenic HMPA as by-product.

Legal Information

PyBOP is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H317,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Laëtitia Fauconnot et al.
Chemistry and physics of lipids, 139(2), 125-136 (2006-01-13)
The chemical synthesis of pure triacylglycerol (TAG) regioisomers, that contain long chain polyunsaturated fatty acids, such as arachidonic acid (AA) or docosahexaenoic acid (DHA), and saturated fatty acids, such as lauric acid (La) or palmitic acid (P), at defined positions
Expanding on the purification methodology of polyethylene glycol (PEG) bound molecules: The synthesis of 3, 5-pyrazolidinediones.
Zhao X-Y, et al.
Tetrahedron Letters, 39(46), 8433-8436 (1998)
PyBOP: A new peptide coupling reagent devoid of toxic by-product.
Coste J, et al.
Tetrahedron Letters, 31(2), 205-208 (1990)
Joshua D Carter et al.
Journal of nucleic acids, 2011, 926595-926595 (2011-10-19)
This work describes preparation strategies for peptide-oligonucleotide conjugates that combine the self-assembling behavior of DNA oligonucleotides with the molecular recognition capabilities of peptides. The syntheses include a solution-phase fragment coupling reaction and a solid-phase fragment coupling strategy where the oligonucleotide
Ting-Jung Chen et al.
Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry, 14(2), 253-260 (2008-11-01)
A novel magnetic resonance imaging (MRI) contrast agent containing Herceptin is reported. The surfaces of superparamagnetic iron oxide nanoparticles were modified with dextran and conjugated with Herceptin (Herceptin-nanoparticles) to improve their dispersion, magnetization, and targeting of the specific receptors on
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