Dendritic physical gels: Structural parameters for gelation with peptide-core dendrimers

Woo Dong Jang, Takuzo Aida

Research output: Contribution to journalArticle

74 Citations (Scopus)

Abstract

Eleven different peptide-core dendritic macromolecules, each having a [G2] poly(benzyl ether) dendritic wedge (Den) at the peptide side chain, N-terminal, or C-terminal, were synthesized, and their potentials as macromolecular organic gelators were investigated in MeCN. Among these candidates, side-chain-dendronized Boc-Tyr(Den)-Ala and cyclo-(Tyr(Den)-Ala) and N-dendronized Den-Phe-Ala and Den-Phe-Ala-OMe (Figure 1) were found to form physical gels with critical concentrations for gelatiori of 1.0-2.2 mM, whereas C-dendronized Boc-Phe-Ala-ODen and Phe-Ala-ODen were unable to induce gelation. FE-SEM micrographs of the dry gels showed the presence of fibrous or ribbonlike self-assembled structures, which melted at 112-214°C (Tm), depending on the modes of hydrogen bonding and van der Waals interactions. Infrared spectroscopy and X-ray diffraction analysis of the dry gels indicated columnar molecular orderings with a rectangular packing geometry for Boc-Tyr(Den)-Ala and Den-Phe-Ala-OMe, while a lamellar geometry for Den-Phe-Ala. Circular dichroism analysis of the transparent gel with Boc-Tyr(Den)-Ala indicated a helically twisted geometry of hydrogen-bonded dipeptide arrays.

Original languageEnglish
Pages (from-to)8461-8469
Number of pages9
JournalMacromolecules
Volume36
Issue number22
DOIs
Publication statusPublished - 2003 Nov 4

Fingerprint

Dendrimers
Gelation
Peptides
Gels
Geometry
Dipeptides
Dichroism
Macromolecules
Ether
X ray diffraction analysis
Hydrogen
Infrared spectroscopy
Ethers
Hydrogen bonds
Scanning electron microscopy
tert-butoxycarbonyl-tyrosine

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

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title = "Dendritic physical gels: Structural parameters for gelation with peptide-core dendrimers",
abstract = "Eleven different peptide-core dendritic macromolecules, each having a [G2] poly(benzyl ether) dendritic wedge (Den) at the peptide side chain, N-terminal, or C-terminal, were synthesized, and their potentials as macromolecular organic gelators were investigated in MeCN. Among these candidates, side-chain-dendronized Boc-Tyr(Den)-Ala and cyclo-(Tyr(Den)-Ala) and N-dendronized Den-Phe-Ala and Den-Phe-Ala-OMe (Figure 1) were found to form physical gels with critical concentrations for gelatiori of 1.0-2.2 mM, whereas C-dendronized Boc-Phe-Ala-ODen and Phe-Ala-ODen were unable to induce gelation. FE-SEM micrographs of the dry gels showed the presence of fibrous or ribbonlike self-assembled structures, which melted at 112-214°C (Tm), depending on the modes of hydrogen bonding and van der Waals interactions. Infrared spectroscopy and X-ray diffraction analysis of the dry gels indicated columnar molecular orderings with a rectangular packing geometry for Boc-Tyr(Den)-Ala and Den-Phe-Ala-OMe, while a lamellar geometry for Den-Phe-Ala. Circular dichroism analysis of the transparent gel with Boc-Tyr(Den)-Ala indicated a helically twisted geometry of hydrogen-bonded dipeptide arrays.",
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Dendritic physical gels : Structural parameters for gelation with peptide-core dendrimers. / Jang, Woo Dong; Aida, Takuzo.

In: Macromolecules, Vol. 36, No. 22, 04.11.2003, p. 8461-8469.

Research output: Contribution to journalArticle

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AB - Eleven different peptide-core dendritic macromolecules, each having a [G2] poly(benzyl ether) dendritic wedge (Den) at the peptide side chain, N-terminal, or C-terminal, were synthesized, and their potentials as macromolecular organic gelators were investigated in MeCN. Among these candidates, side-chain-dendronized Boc-Tyr(Den)-Ala and cyclo-(Tyr(Den)-Ala) and N-dendronized Den-Phe-Ala and Den-Phe-Ala-OMe (Figure 1) were found to form physical gels with critical concentrations for gelatiori of 1.0-2.2 mM, whereas C-dendronized Boc-Phe-Ala-ODen and Phe-Ala-ODen were unable to induce gelation. FE-SEM micrographs of the dry gels showed the presence of fibrous or ribbonlike self-assembled structures, which melted at 112-214°C (Tm), depending on the modes of hydrogen bonding and van der Waals interactions. Infrared spectroscopy and X-ray diffraction analysis of the dry gels indicated columnar molecular orderings with a rectangular packing geometry for Boc-Tyr(Den)-Ala and Den-Phe-Ala-OMe, while a lamellar geometry for Den-Phe-Ala. Circular dichroism analysis of the transparent gel with Boc-Tyr(Den)-Ala indicated a helically twisted geometry of hydrogen-bonded dipeptide arrays.

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