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Hexadecameric self-assembled dendrimers built from 2'-deoxyguanosine derivatives.

Betancourt JE, Rivera JM - Org. Lett. (2008)

Bottom Line: Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits.The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction.Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Puerto Rico, Río Piedras Campus, Río Piedras, Puerto Rico.

ABSTRACT
Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits. The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction. Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

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1H NMR spectra (500 MHz, CD3CN, 298 K, 0.5 equiv of KI) of (a) (mAGD2)16 and (b) (mAGD3)16.
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fig3: 1H NMR spectra (500 MHz, CD3CN, 298 K, 0.5 equiv of KI) of (a) (mAGD2)16 and (b) (mAGD3)16.

Mentions: Both derivatives mAGD2 and mAGD3 show sharp and well-defined signals in DMSO-d6, which is indicative of mostly noninteracting monomeric species and expected with such a highly competitive solvent. Similarly, in CD3CN all peaks are sharp and well-resolved with the exception of the N1H peaks, which are slightly exchange-broadened, indicating the formation of loosely bound aggregates (Supporting Information, Figures S1 and S2). For both compounds, addition of 0.0625 equiv of KI induces the appearance of a new set of peaks that are sharper and correspond to the formation of an octamer. Further addition of KI (0.125−0.5 equiv) leads in both cases to the appearance of a hexadecamer as evidenced by the splitting of every signal of the spectrum into pairs of peaks. For both mAGD2 and mAGD3, the difference in the chemical shift for the imino (N1H) protons of the inner and outer tetrads is about 1.6 ppm, reflecting the anisotropic shielding of the inner tetrads relative to the outer tetrads (Figure 3).


Hexadecameric self-assembled dendrimers built from 2'-deoxyguanosine derivatives.

Betancourt JE, Rivera JM - Org. Lett. (2008)

1H NMR spectra (500 MHz, CD3CN, 298 K, 0.5 equiv of KI) of (a) (mAGD2)16 and (b) (mAGD3)16.
© Copyright Policy - open-access - ccc-price
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC2654094&req=5

fig3: 1H NMR spectra (500 MHz, CD3CN, 298 K, 0.5 equiv of KI) of (a) (mAGD2)16 and (b) (mAGD3)16.
Mentions: Both derivatives mAGD2 and mAGD3 show sharp and well-defined signals in DMSO-d6, which is indicative of mostly noninteracting monomeric species and expected with such a highly competitive solvent. Similarly, in CD3CN all peaks are sharp and well-resolved with the exception of the N1H peaks, which are slightly exchange-broadened, indicating the formation of loosely bound aggregates (Supporting Information, Figures S1 and S2). For both compounds, addition of 0.0625 equiv of KI induces the appearance of a new set of peaks that are sharper and correspond to the formation of an octamer. Further addition of KI (0.125−0.5 equiv) leads in both cases to the appearance of a hexadecamer as evidenced by the splitting of every signal of the spectrum into pairs of peaks. For both mAGD2 and mAGD3, the difference in the chemical shift for the imino (N1H) protons of the inner and outer tetrads is about 1.6 ppm, reflecting the anisotropic shielding of the inner tetrads relative to the outer tetrads (Figure 3).

Bottom Line: Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits.The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction.Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, University of Puerto Rico, Río Piedras Campus, Río Piedras, Puerto Rico.

ABSTRACT
Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) subunits. The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction. Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.

Show MeSH