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. Author manuscript; available in PMC: 2011 Jul 21.

Published in final edited form as: Bioconjug Chem. 2010 Jul 21;21(7):1190–1205. doi: 10.1021/bc900569u

Scheme 5 — Coupling of P2Y₁ receptor antagonists to PAMAM dendrimers in a manner that preserves the interaction with the receptor. (A) Attempted use of the Sonogashira reaction to couple a 2-iodoadenine derivative to a terminal alkyne G3 dendrimer. Reagents and conditions: (i) HATU, 4-pentynoic acid, DIEA, DMF (ii) CuI, (Ph3P)₂PdCl₂,TEA, DMF, rt. (B) Attempted coupling of a 2-amine derivatized nucleotide to a terminal carboxylic acid G2.5 dendrimer. Reagents: (i) Compound 30, HATU, DIEA, DMSO. (C) Successful use of click chemistry to couple an alkyne-functionalized, protected nucleotide derivative to a terminal azido-bearing G4 dendrimer to yield dendrimer conjugate 53 (MRS2966). Reagents: (i) CuSO₄ aq., sodium ascorbate; (ii) TFA.

Scheme 5 — Coupling of P2Y₁ receptor antagonists to PAMAM dendrimers in a manner that preserves the interaction with the receptor. (A) Attempted use of the Sonogashira reaction to couple a 2-iodoadenine derivative to a terminal alkyne G3 dendrimer. Reagents and conditions: (i) HATU, 4-pentynoic acid, DIEA, DMF (ii) CuI, (Ph3P)₂PdCl₂,TEA, DMF, rt. (B) Attempted coupling of a 2-amine derivatized nucleotide to a terminal carboxylic acid G2.5 dendrimer. Reagents: (i) Compound 30, HATU, DIEA, DMSO. (C) Successful use of click chemistry to couple an alkyne-functionalized, protected nucleotide derivative to a terminal azido-bearing G4 dendrimer to yield dendrimer conjugate 53 (MRS2966). Reagents: (i) CuSO₄ aq., sodium ascorbate; (ii) TFA.