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( A ) Previously developed sulfonyl‐based solid support strategy for the incorporation of amino modifiers ( S ‐CPG). In some implementations, S ‐CPG can also be conjugated to the solid support through a carbamate linkage. ( B ) This work focuses on the use of CPR II CPG to incorporate amino modifiers via initial activation with N , N ′‐disuccinimidyl carbonate (DSC), generating R ‐CPG. A trifunctional ligand (protected <t>1,3‐diamino‐2‐propanol)</t> enables anchoring to the solid support, followed by selective conjugation at the amine and subsequent strand elongation from the hydroxyl group.
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( A ) Previously developed sulfonyl‐based solid support strategy for the incorporation of amino modifiers ( S ‐CPG). In some implementations, S ‐CPG can also be conjugated to the solid support through a carbamate linkage. ( B ) This work focuses on the use of CPR II CPG to incorporate amino modifiers via initial activation with N , N ′‐disuccinimidyl carbonate (DSC), generating R ‐CPG. A trifunctional ligand (protected 1,3‐diamino‐2‐propanol) enables anchoring to the solid support, followed by selective conjugation at the amine and subsequent strand elongation from the hydroxyl group.

Journal: Current Protocols

Article Title: A Facile Strategy for 3′‐Terminal Functionalization of DNA and RNA via On‐Column Conjugation with Integration into Tandem Oligonucleotide Synthesis

doi: 10.1002/cpz1.70374

Figure Lengend Snippet: ( A ) Previously developed sulfonyl‐based solid support strategy for the incorporation of amino modifiers ( S ‐CPG). In some implementations, S ‐CPG can also be conjugated to the solid support through a carbamate linkage. ( B ) This work focuses on the use of CPR II CPG to incorporate amino modifiers via initial activation with N , N ′‐disuccinimidyl carbonate (DSC), generating R ‐CPG. A trifunctional ligand (protected 1,3‐diamino‐2‐propanol) enables anchoring to the solid support, followed by selective conjugation at the amine and subsequent strand elongation from the hydroxyl group.

Article Snippet: Argon gas 1,3‐Diamino‐2‐propanol (Fisher Scientific, cat. no. AAA1961809) 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU; Combi‐Blocks, cat. no. QA‐1443) 4‐Methoxytrityl chloride (MMTr‐Cl; Tokyo Chemical Industry, cat. no. M0790) Dichloromethane (DCM; ACS grade, Sigma‐Aldrich, cat. no. 34856) Methanol (MeOH; HPLC grade, Sigma‐Aldrich, cat. no. 34860) Silica gel (60 Å, 230‐400 mesh; Fisher Chemical, S82525) Deuterated DMSO (DMSO‐d 6 ; Sigma‐Aldrich, cat. no. 151874‐10 × 0.75ML) 2,5‐Dioxopyrrolidin‐1‐yl 2‐(prop‐2‐yn‐1‐yloxy)acetate (NHS‐ester propargyl; Combi‐Blocks, cat. no. JP‐4311) 200 mM HEPES buffer, pH 8 4 × 35‐cm (diameter × height) flash chromatography column 300‐MHz nuclear magnetic resonance (NMR) instrument (other instruments may be used)

Techniques: Activation Assay, Conjugation Assay

Synthesis of protected 1,3‐diamino‐2‐propanol ( A ) for on‐column coupling and subsequent conjugation using NHS‐ester chemistry, illustrated here with propargyl ( B ).

Journal: Current Protocols

Article Title: A Facile Strategy for 3′‐Terminal Functionalization of DNA and RNA via On‐Column Conjugation with Integration into Tandem Oligonucleotide Synthesis

doi: 10.1002/cpz1.70374

Figure Lengend Snippet: Synthesis of protected 1,3‐diamino‐2‐propanol ( A ) for on‐column coupling and subsequent conjugation using NHS‐ester chemistry, illustrated here with propargyl ( B ).

Article Snippet: Argon gas 1,3‐Diamino‐2‐propanol (Fisher Scientific, cat. no. AAA1961809) 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU; Combi‐Blocks, cat. no. QA‐1443) 4‐Methoxytrityl chloride (MMTr‐Cl; Tokyo Chemical Industry, cat. no. M0790) Dichloromethane (DCM; ACS grade, Sigma‐Aldrich, cat. no. 34856) Methanol (MeOH; HPLC grade, Sigma‐Aldrich, cat. no. 34860) Silica gel (60 Å, 230‐400 mesh; Fisher Chemical, S82525) Deuterated DMSO (DMSO‐d 6 ; Sigma‐Aldrich, cat. no. 151874‐10 × 0.75ML) 2,5‐Dioxopyrrolidin‐1‐yl 2‐(prop‐2‐yn‐1‐yloxy)acetate (NHS‐ester propargyl; Combi‐Blocks, cat. no. JP‐4311) 200 mM HEPES buffer, pH 8 4 × 35‐cm (diameter × height) flash chromatography column 300‐MHz nuclear magnetic resonance (NMR) instrument (other instruments may be used)

Techniques: Conjugation Assay