Copper-Free Click Chemistry

At Glen Research, our goal was to offer a copper-free click phosphoramidite reagent with the following properties:

  • Simple to use
  • Stable in solution on the synthesizer
  • Stable to ammonium hydroxide and AMA<
  • Excellent click performance in 17 hours or less at room temperature

From the variety of cyclooctyne-based copper-free click reagents so far described, we have chosen to offer compounds based on a dibenzo-cyclooctyne (DBCO) structure. We are offering 5'-DBCO-TEG Phosphoramidite for preparing oligos with a 5'-DBCO modification and DBCO-dT-CE Phosphoramidite for inserting a DBCO group at any position within the oligonucleotide. DBCO-sulfo-NHS Ester is also offered for post-synthesis conjugation reactions. DBCO-modified oligos may be conjugated with azides in organic solvents, such as DMSO, or aqeous buffers. Depending on the azide used, the reaction will go to completion in 4-17 hours at room temperature. Simple desalting on a Glen Gel-Pak™ leads to a product with virtually quantitative conjugation efficiency.

Note: We now recommend that synthesis of oligos containing DBCO-dT be completed using 0.5 M CSO in anhydrous acetonitrile (40-4632-xx). Acceptable results can be achieved with iodine oxidation if DBCO-dT is subjected to no more than 8-10 cycles.

4 Product Results
 
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  • DBCO-dT-CE Phosphoramidite
    DBCO-dT-CE Phosphoramidite (10-1539)
    Catalog #: 10-1539
    Formal Name:

    5'-Dimethoxytrityl-5-[(6-oxo-6-(dibenzo[b,f]azacyclooct-4-yn-1-yl)-capramido-N-hex-6-yl)-3-acrylimido]-2'-deoxyUridine,3'-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite

  • 5'-DBCO-TEG Phosphoramidite
    5'-DBCO-TEG Phosphoramidite (10-1941)
    Catalog #: 10-1941
    Formal Name:

    10-(6-oxo-6-(dibenzo[b,f]azacyclooct-4-yn-1-yl)-capramido-N-ethyl)-O-triethyleneglycol-1-[(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite

  • DBCO-sulfo-NHS Ester
    DBCO-sulfo-NHS Ester (50-1941)
    Catalog #: 50-1941
    Formal Name:

    6-oxo-6-(dibenzo[b,f]azacyclooct-4-yn-1-yl)-caproic acid sulfo-N-hydroxysuccinimide ester, sodium salt

  • DBCO-Serinol Phosphoramidite
    DBCO-Serinol Phosphoramidite (10-1998)
    Catalog #: 10-1998
    Formal Name:

    3-Dimethoxytrityloxy-2-(6-oxo-6-(dibenzo[b,f]azacyclooct-4-yn-1-yl)-capramido)propyl-1-O-(2-cyanoethyl)-(N,N-diisopropyl)-phosphoramidite

 
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