Description
t-Boc-N-Amido-PEG2-amine is a PEG linker containing an amino group and Boc-protected amino group. The hydrophilic PEG spacer increases solubility in aqueous media. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The Boc group can be deprotected under mild acidic conditions to form the free amine.
Chemical Properties
Light yellow oil
Uses
Linker reagent for the prep. of a broad variety of linked tags, monomers for polymerisation, ionophores etc., e.g. biotinylation reagents.
reaction suitability
reagent type: cross-linking reagent
Synthesis
General procedure: A dichloromethane solution (10 mL/mmol) of 1,8-diamino-3,6-dioxaoctane (1 eq.) was treated with di-tert-butyl dicarbonate (0.15 eq.) at 0 °C, kept at 0 °C for 5 hours, and then the reaction was continued at room temperature for 18 hours. Upon completion of the reaction, the organic phase was washed with water until all unreacted 1,8-diamino-3,6-dioxaoctane was removed by extraction. The organic phase was dried over anhydrous magnesium sulfate and recovered quantitatively to give the Boc-protected product tert-butyl 2-(2-(2-aminoethoxy)ethoxy)ethylcarbamate, which was concentrated under vacuum. The product characterization data were as follows:11a: 1H NMR (300 MHz, CDCl3): δ 1.45 (s, 9H), 1.80 (br m, 2H, NH2), 3.25 (m, 2H), 3.38 (m, 2H), 3.50-3.70 (m, 8H), 5.10 (br s, 1H, NHCO2).11b: 1H NMR ( 300 MHz, CDCl3): δ 1.42 (s, 9H), 1.75 (br m, 2H, NH2), 2.84 (t, 2H, J = 5.3 Hz), 3.29 (m, 2H), 3.51 (m, 4H), 3.58 (sharp m, 8H), 5.30 (br s, 1H, NHCO2).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4208 - 4212
[2] Tetrahedron, 2012, vol. 68, # 52, p. 10818 - 10826
[3] Journal of Medicinal Chemistry, 1994, vol. 37, # 17, p. 2678 - 2685
[4] Journal of the American Chemical Society, 2013, vol. 135, # 34, p. 12684 - 12689
[5] Tetrahedron, 2017, vol. 73, # 33, p. 4972 - 4978
