1,1,1-Trifluoroethyl-PEG2-azide - CAS 1835759-68-6

1,1,1-Trifluoroethyl-PEG2-azide is a crosslinker containing an azide group and a trifluroethyl group. The azide group can participate in Click Chemistry reactions with reagents such as alkynes, DBCO and BCN. The hydrophilic PEG spacer increases solubility in aqueous media. The trifluoroethyl group is used to react with lysine and other primary amine groups in proteins, antibodies, and other molecules and surfaces.

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Molecular Formula
C6H10F3N3O2
Molecular Weight
213.16

1,1,1-Trifluoroethyl-PEG2-azide

    • Specification
      • Purity
        ≥95%
        Solubility
        Soluble in DMSO
        Appearance
        Pale Yellow Oily Matter
        Storage
        Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
        Shipping
        Room temperature in continental US; may vary elsewhere.
        IUPAC Name
        2-[2-(2-azidoethoxy)ethoxy]-1,1,1-trifluoroethane
        Synonyms
        Ethane, 2-[2-(2-azidoethoxy)ethoxy]-1,1,1-trifluoro-; Ethane, 1-(2-azidoethoxy)-2-(2,2,2-trifluoroethoxy)-; HUN59686; HUN-59686; HUN 59686
    • Properties
      • InChI Key
        HSRLFQUDMWNYCB-UHFFFAOYSA-N
        InChI
        InChI=1S/C6H10F3N3O2/c7-6(8,9)5-14-4-3-13-2-1-11-12-10/h1-5H2
        Canonical SMILES
        C(COCCOCC(F)(F)F)N=[N+]=[N-]
    • Reference Reading
      • 1. Electrophilic Activation of [1.1.1]Propellane for the Synthesis of Nitrogen-Substituted Bicyclo[1.1.1]pentanes
        Sarah Livesley, Alistair J Sterling, Craig M Robertson, William R F Goundry, James A Morris, Fernanda Duarte, Christophe Aïssa Angew Chem Int Ed Engl. 2022 Jan 10;61(2):e202111291. doi: 10.1002/anie.202111291.Epub 2021 Nov 26.
        Strategies commonly used for the synthesis of functionalised bicyclo[1.1.1]pentanes (BCP) rely on the reaction of [1.1.1]propellane with anionic or radical intermediates. In contrast, electrophilic activation has remained a considerable challenge due to the facile decomposition of BCP cations, which has severely limited the applications of this strategy. Herein, we report the electrophilic activation of [1.1.1]propellane in a halogen bond complex, which enables its reaction with electron-neutral nucleophiles such as anilines and azoles to give nitrogen-substituted BCPs that are prominent motifs in drug discovery. A detailed computational analysis indicates that the key halogen bonding interaction promotes nucleophilic attack without sacrificing cage stabilisation. Overall, our work rehabilitates electrophilic activation of [1.1.1]propellane as a valuable strategy for accessing functionalised BCPs.
        2. Skeletal muscle CaV1.1 channelopathies
        Bernhard E Flucher Pflugers Arch. 2020 Jul;472(7):739-754. doi: 10.1007/s00424-020-02368-3.Epub 2020 Mar 28.
        CaV1.1 is specifically expressed in skeletal muscle where it functions as voltage sensor of skeletal muscle excitation-contraction (EC) coupling independently of its functions as L-type calcium channel. Consequently, all known CaV1.1-related diseases are muscle diseases and the molecular and cellular disease mechanisms relate to the dual functions of CaV1.1 in this tissue. To date, four types of muscle diseases are known that can be linked to mutations in the CACNA1S gene or to splicing defects. These are hypo- and normokalemic periodic paralysis, malignant hyperthermia susceptibility, CaV1.1-related myopathies, and myotonic dystrophy type 1. In addition, the CaV1.1 function in EC coupling is perturbed in Native American myopathy, arising from mutations in the CaV1.1-associated protein STAC3. Here, we first address general considerations concerning the possible roles of CaV1.1 in disease and then discuss the state of the art regarding the pathophysiology of the CaV1.1-related skeletal muscle diseases with an emphasis on molecular disease mechanisms.
        3. Tellurophene-Containing Core-Modified Pentaphyrin(2.1.1.1.1)s
        Md Ashif Ali, Kandala Laxman, Kamakshya Nath Panda, Mangalampalli Ravikanth J Org Chem. 2022 Mar 4;87(5):2480-2488. doi: 10.1021/acs.joc.1c02384.Epub 2022 Jan 26.
        Various core-modified tellurophene-containing pentaphyrin(2.1.1.1.1)s were synthesized via (3 + 2) condensation of 16-telluratripyrrane with different heterodiols under mild acid catalyzed conditions in 5-12% yields. The formation of pentaphyrin (2.1.1.1.1) with a N2O2Te core was not successful due to its inherent instability. The new pentaphyrins were characterized and studied by HR-MS, 1D and 2D NMR, X-ray crystallography for one of the pentaphyrins, absorption and DFT/TD-DFT techniques. The NMR studies indicated their nonaromatic nature. The X-ray structure obtained for pentaphyrin(2.1.1.1.1) with N4Te core revealed that the macrocycle exists in a highly distorted nonplanar structure. The DFT studies showed that the macrocycles are nonaromatic and exists in highly distorted nonplanar geometry. Furthermore, as the core heterocyclic groups at ethene moiety were changed from pyrrole to furan to thiophene to benzene, the macrocycles tended toward more planar structures. The absorption spectra of pentaphyrins showed one strong sharp band in the region of 450-540 nm along with a broad band in the region of 700-800 nm. The pentaphyrin(2.1.1.1.1) with N4Te core upon protonation showed distinct color change in solution and large bathochromic shifts in absorption bands with an absorption in the NIR region.
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