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. Colloid Polymer Science Springer Journals

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

Loading next page...
Springer Berlin Heidelberg
Copyright © 2017 by Springer-Verlag Berlin Heidelberg
Chemistry; Polymer Sciences; Soft and Granular Matter, Complex Fluids and Microfluidics; Characterization and Evaluation of Materials; Physical Chemistry; Food Science; Nanotechnology and Microengineering
Publisher site
See Article on Publisher Site


You’re reading a free preview. Subscribe to read the entire article.

DeepDyve is your
personal research library

It’s your single place to instantly
discover and read the research
that matters to you.

Enjoy affordable access to
over 12 million articles from more than
10,000 peer-reviewed journals.

All for just $49/month

Explore the DeepDyve Library

Unlimited reading

Read as many articles as you need. Full articles with original layout, charts and figures. Read online, from anywhere.

Stay up to date

Keep up with your field with Personalized Recommendations and Follow Journals to get automatic updates.

Organize your research

It’s easy to organize your research with our built-in tools.

Your journals are on DeepDyve

Read from thousands of the leading scholarly journals from SpringerNature, Elsevier, Wiley-Blackwell, Oxford University Press and more.

All the latest content is available, no embargo periods.

See the journals in your area

Monthly Plan

  • Read unlimited articles
  • Personalized recommendations
  • No expiration
  • Print 20 pages per month
  • 20% off on PDF purchases
  • Organize your research
  • Get updates on your journals and topic searches


Start Free Trial

14-day Free Trial

Best Deal — 39% off

Annual Plan

  • All the features of the Professional Plan, but for 39% off!
  • Billed annually
  • No expiration
  • For the normal price of 10 articles elsewhere, you get one full year of unlimited access to articles.



billed annually
Start Free Trial

14-day Free Trial