An additional fluorenylmethoxycarbonyl (Fmoc) moiety in di-Fmoc-functionalized L-lysine induces pH-controlled ambidextrous gelation with significant advantages

Soft Matter
Samala Murali Mohan ReddyAsit Baran Mandal

Abstract

In recent years, several fluorenylmethoxycarbonyl (Fmoc)-functionalized amino acids and peptides have been used to construct hydrogels, which find a wide range of applications. Although several hydrogels have been prepared from mono Fmoc-functionalized amino acids, herein, we demonstrate the importance of an additional Fmoc-moiety in the hydrogelation of double Fmoc-functionalized L-lysine [Fmoc(Nα)-L-lysine(NεFmoc)-OH, (Fmoc-K(Fmoc))] as a low molecular weight gelator (LMWG). Unlike other Fmoc-functionalized amino acid gelators, Fmoc-K(Fmoc) exhibits pH-controlled ambidextrous gelation (hydrogelation at different pH values as well as organogelation), which is significant among the gelators. Distinct fibrous morphologies were observed for Fmoc-K(Fmoc) hydrogels formed at different pH values, which are different from organogels in which Fmoc-K(Fmoc) showed bundles of long fibers. In both hydrogels and organogels, the self-assembly of Fmoc-K(Fmoc) was driven by aromatic π-π stacking and hydrogen bonding interactions, as evidenced from spectroscopic analyses. Characterization of Fmoc-K(Fmoc) gels using several biophysical methods indicates that Fmoc-K(Fmoc) has several advantages and significant importance as a LMWG. The advantage...Continue Reading

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Citations

Mar 28, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Samala Murali Mohan ReddyGanesh Shanmugam
Jul 18, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Seyed Meysam Hashemnejad, Santanu Kundu
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Feb 20, 2020·Biomaterials Science·Avinash Yashwant GahaneAshwani Kumar Thakur
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Dec 7, 2018·Chemical Communications : Chem Comm·Santanu Panja, Dave J Adams
Feb 20, 2021·Angewandte Chemie·Santanu PanjaDave J Adams
Apr 17, 2021·Chemistry : a European Journal·Santanu Panja, Dave J Adams
Nov 15, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Samala Murali Mohan ReddyGanesh Shanmugam
May 5, 2017·ACS Omega·Seyed Meysam HashemnejadSantanu Kundu
Dec 16, 2020·ACS Biomaterials Science & Engineering·Neelam Chauhan, Yashveer Singh
Oct 28, 2020·Langmuir : the ACS Journal of Surfaces and Colloids·Koduvayur A RamyaAbhijit P Deshpande
Sep 2, 2021·Chemistry : a European Journal·Souvik MisraJayanta Nanda

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