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Perfluorophenyl 2-(cyclooct-2-ynyloxy)acetate

  CAS No.: 886209-60-5   Cat No.: BADC-00426   Purity: ≥95% 4.5  

Perfluorophenyl 2-(cyclooct-2-ynyloxy)acetate is a cleavable ADC junction bridge for the synthesis of antibody drug conjugates (ADCs). It is a chemical compound used in click chemistry and bioconjugation applications. It features a cyclooctyne moiety, which is a reactive cyclic alkyne with a strained ring structure, making it highly reactive in strain-promoted alkyne-azide cycloaddition (SPAAC) reactions. The O-PFP (pentafluorophenyl) ester group is a reactive functional group that facilitates the attachment of this molecule to other biomolecules or surfaces. This compound is often used for labeling, imaging, or creating bioconjugates in chemical biology and drug development.

Perfluorophenyl 2-(cyclooct-2-ynyloxy)acetate

Structure of 886209-60-5

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Category
ADC Linker
Molecular Formula
C16H13F5O3
Molecular Weight
348.26
Shipping
Room temperature
Shipping
Store at -20 °C

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Synonyms
Perfluorophenyl 2-(cyclooct-2-yn-1-yloxy)acetate; Cyclooctyne-OPFP; Cyclooctyne-O-PFP ester; Acetic acid, 2-(2-cyclooctyn-1-yloxy)-, 2,3,4,5,6-pentafluorophenyl ester; 2,3,4,5,6-Pentafluorophenyl 2-(2-cyclooctyn-1-yloxy)acetate; Acetic acid, (2-cyclooctyn-1-yloxy)-, pentafluorophenyl ester; 2,3,4,5,6-pentafluorophenyl 2-(cyclooct-2-yn-1-yloxy)acetate
IUPAC Name
(2,3,4,5,6-pentafluorophenyl) 2-cyclooct-2-yn-1-yloxyacetate
Canonical SMILES
C1CCC#CC(CC1)OCC(=O)OC2=C(C(=C(C(=C2F)F)F)F)F
InChI
InChI=1S/C16H13F5O3/c17-11-12(18)14(20)16(15(21)13(11)19)24-10(22)8-23-9-6-4-2-1-3-5-7-9/h9H,1-4,6,8H2
InChIKey
FTKRNGMQMZGSDF-UHFFFAOYSA-N
Density
1.38±0.1 g/cm3
Solubility
Soluble in DMSO
Appearance
White to cream-white oily substance
Shipping
Room temperature
Storage
Store at -20 °C
Boiling Point
384.9±42.0 °C at 760 mmHg
1. Photoaffinity analogues of farnesyl pyrophosphate transferable by protein farnesyl transferase
Carol A Fierke, Richard J Isaacs, Katherine E Bowers, Kareem A H Chehade, Douglas A Andres, Jennifer S Pickett, H Peter Spielmann, Katarzyna Kiegiel J Am Chem Soc . 2002 Jul 17;124(28):8206-19. doi: 10.1021/ja0124717.
Farnesylation is a posttranslational lipid modification in which a 15-carbon farnesyl isoprenoid is linked via a thioether bond to specific cysteine residues of proteins in a reaction catalyzed by protein farnesyltransferase (FTase). We synthesized analogues (3-6) of farnesyl pyrophosphate (FPP) to probe the range of modifications possible to the FPP skeleton which allow for efficient transfer by FTase. Photoaffinity analogues of FPP (5, 6) were prepared by substituting perfluorophenyl azide functional groups for the omega-terminal isoprene of FPP. Substituted anilines replace the omega-terminal isoprene in analogues 3 and 4. Compounds 3-5 were prepared by reductive amination of the appropriate anilines with 8-oxo-geranyl acetate, followed by ester hydrolysis, chlorination, and pyrophosphorylation. Additional substitution of three methylenes for the beta-isoprene of FPP gave photoprobe 6 in nine steps. Preparation of the analogues required TiCl(4)-mediated imine formation prior to NaBH(OAc)(3) reduction for anilines with a pK(a) < 1. The azide moiety was not affected by Ph(3)PCl(2) conversion of allylic alcohols 13-16 into corresponding chlorides 17-20. Analogues 3-6 are efficiently transferred to target N-dansyl-GCVLS peptide substrate by mammalian FTase. Comparison of analogue structures and kinetics of transfer to those of FPP reveals that ring fluorination and para substituents have little effect on the affinity of the analogue pyrophosphate for FTase and its transfer efficiency. These results are also supported with models of the analogue binding modes in the active site of FTase. The transferable azide photoprobe 5 photoinactivates FTase. Transferable analogues 5 and 6 allow the formation of appropriately posttranslationally modified photoreactive peptide probes of isoprene function.
2. On the hydrolysis of diethyl 2-(perfluorophenyl)malonate
Ilya V Taydakov, Mikhail A Kiskin Beilstein J Org Chem . 2020 Jul 28;16:1863-1868. doi: 10.3762/bjoc.16.153.
Diethyl 2-(perfluorophenyl)malonate was synthesized in 47% isolated yield by the reaction of sodium diethyl malonate and hexafluorobenzene. The resulting compound was considered as a starting material for synthesizing 2-(perfluorophenyl)malonic acid by hydrolysis. It was found that the desired 2-(perfluorophenyl)malonic acid could not be obtained from this ester by hydrolysis, neither under basic nor under acidic conditions. Nevertheless, hydrolysis of the ester with a mixture of HBr and AcOH gave 2-(perfluorophenyl)acetic acid in a good preparative yield of 63%. A significant advantage of this new approach to 2-(perfluorophenyl)acetic acid is that handling toxic substances such as cyanides and perfluorinated benzyl halides is avoided.
3. Anion-binding catalysis by electron-deficient pyridinium cations
Somnath Das, Daniel Pekel, Albrecht Berkessel, Jörg-M Neudörfl Angew Chem Int Ed Engl . 2014 Oct 20;53(43):11660-4. doi: 10.1002/anie.201403778.
A new activation principle in organocatalysis is presented: halide binding through Coulombic interactions. This mode of catalysis was realized by using 3,5-di(carbomethoxy)pyridinium ions that carry an additional electron-withdrawing substituent on the nitrogen atom, for example, pentafluorobenzyl or cyanomethyl. For the N-pentafluorobenzyl derivative, Coulombic interaction with the pyridinium moiety is complemented in the solid state by anion-π interactions with the perfluorophenyl ring. Bromide and chloride are bound by these cations in a 1:1 stoichiometry. Catalysis of the C-C coupling between 1-chloroisochroman (and related electrophiles) with silyl ketene acetals occurs at -78 °C and at low catalyst loading (2 mol%).

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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