Synthesis and gelation capability of mono- and disubstituted cyclo(L-Glu-L-Glu) derivatives with tyramine, tyrosine and phenylalanine

Synthesis and gelation capability of mono- and disubstituted cyclo(L-Glu-L-Glu) derivatives with... A series of mono- and disubstituted glutamic cyclic dipeptide derivatives (cyclo(L-Glu-Glu)s) with tyramine, tyrosine, and phenylalanine (3–12) were synthesized and investigated as organo- and hydrogelators. Unexpectedly, both tyramine mono- and disubstituted cyclo(L-Glu-Glu)s showed no gelation toward all the selected organic solvents, phosphate-buffered saline (PBS), and water. However, those t-butyloxy (OtBu) protecting tyrosine and phenylalanine mono- and disubstituted cyclo(L-Glu-Glu)s in general presented a diversified gelation capability. Interestingly, the OtBu protecting tyrosine monosubstituted 10 enabled to gel PBS and water featuring a minimum gel concentration (MGC) of 1.0 and 2 wt% at room temperature, respectively. Furthermore, its hydrogelation in PBS can sustain to 44 °C at a concentration of 3 wt% under ultrasonication. After the deproction of OtBu groups, the phenylalanine monosubstituted 8 and tyrosine disubstituted 11 are only capable of gelling acetone showing a MGC of 2.0 and 3.0 wt%. A variety of self-assembled fibrous 3D networks were visible in the resulting organo- and hydrogels by TEM and SEM observations. Rheological measurements demonstrated the viscoelastic characteristics of all the gels. FTIR and fluorescence analyses also revealed that the intermolecular hydrogen bonding and π–π stacking interactions jointly play as major driving forces to promote those tyrosine and phenylalanine monosubstituted cyclo(L-Glu-Glu)s to self-assemble into intermeshing 3D network structures immobilizing a vast amount of organic solvent molecules. It was noted that a careful balance between the hydrophilicity and hydrophobicity as well as the hydrogen bonding interactions in 10 make a great contribution to the hydrogelation process. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Colloid Polymer Science Springer Journals

Synthesis and gelation capability of mono- and disubstituted cyclo(L-Glu-L-Glu) derivatives with tyramine, tyrosine and phenylalanine

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Publisher
Springer Berlin Heidelberg
Copyright
Copyright © 2017 by Springer-Verlag Berlin Heidelberg
Subject
Chemistry; Polymer Sciences; Soft and Granular Matter, Complex Fluids and Microfluidics; Characterization and Evaluation of Materials; Physical Chemistry; Food Science; Nanotechnology and Microengineering
ISSN
0303-402X
eISSN
1435-1536
D.O.I.
10.1007/s00396-017-4120-y
Publisher site
See Article on Publisher Site

Abstract

A series of mono- and disubstituted glutamic cyclic dipeptide derivatives (cyclo(L-Glu-Glu)s) with tyramine, tyrosine, and phenylalanine (3–12) were synthesized and investigated as organo- and hydrogelators. Unexpectedly, both tyramine mono- and disubstituted cyclo(L-Glu-Glu)s showed no gelation toward all the selected organic solvents, phosphate-buffered saline (PBS), and water. However, those t-butyloxy (OtBu) protecting tyrosine and phenylalanine mono- and disubstituted cyclo(L-Glu-Glu)s in general presented a diversified gelation capability. Interestingly, the OtBu protecting tyrosine monosubstituted 10 enabled to gel PBS and water featuring a minimum gel concentration (MGC) of 1.0 and 2 wt% at room temperature, respectively. Furthermore, its hydrogelation in PBS can sustain to 44 °C at a concentration of 3 wt% under ultrasonication. After the deproction of OtBu groups, the phenylalanine monosubstituted 8 and tyrosine disubstituted 11 are only capable of gelling acetone showing a MGC of 2.0 and 3.0 wt%. A variety of self-assembled fibrous 3D networks were visible in the resulting organo- and hydrogels by TEM and SEM observations. Rheological measurements demonstrated the viscoelastic characteristics of all the gels. FTIR and fluorescence analyses also revealed that the intermolecular hydrogen bonding and π–π stacking interactions jointly play as major driving forces to promote those tyrosine and phenylalanine monosubstituted cyclo(L-Glu-Glu)s to self-assemble into intermeshing 3D network structures immobilizing a vast amount of organic solvent molecules. It was noted that a careful balance between the hydrophilicity and hydrophobicity as well as the hydrogen bonding interactions in 10 make a great contribution to the hydrogelation process.

Journal

Colloid Polymer ScienceSpringer Journals

Published: Jun 27, 2017

References

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