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Pentapeptide Based Organogels: The Role of Adjacently Located Phenylalanine Residues in Gel Formation

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Title Pentapeptide Based Organogels: The Role of Adjacently Located Phenylalanine Residues in Gel Formation
 
Creator Banerjee, Arijit
Palui, Goutam
Banerjee, Arindam
 
Subject Chemistry
 
Description A terminally protected self-assembling pentapeptide Boc-Leu(1)-Val(2)-Phe(3)-Phe(4)-Ala(5)-OMe 1
bearing sequence similarity with Ab17–21 (the fragment 17–21 of the amyloid b-peptide Ab42) forms
thermoreversible transparent gels in various organic solvents including benzene, toluene, m-xylene and
1,2-dichlorobenzene. A series of its variants have been synthesized in order to study the role of
adjacently located phenylalanine residues and the protecting groups for gelation in different organic
solvents. Replacement of any of the Phe residues of the Phe-Phe segment with any other hydrophobic
a-amino acid residue drastically changes the gel forming properties indicating that both Phe residues
have an important role in gel formation. These gels are characterised using field emission scaning
electron microscopy (FE-SEM), transmission electron microscopy (TEM), FT-IR and wide angle
X-ray scattering (WAXS) studies. WAXS studies of the peptide 1–benzene gel indicate that p–p
interaction is responsible for gel formation and it reveals the necessity of the Phe residues in gel
formation. Transmission electron microscopy (TEM) of the gels reveals a nanofibrillar morphology,
which is obtained from the self-assembled gelators in the gel phase. These gels bind with a physiological
dye, Congo red, and show a green birefringence under cross polarizers, which is a characteristic feature
of amyloid fibrils.
 
Date 2008
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/184/1/SOFT_MATTER%2C_4_(7)%2C1430%2D1437%2C2008_[151].pdf
Banerjee, Arijit and Palui, Goutam and Banerjee, Arindam (2008) Pentapeptide Based Organogels: The Role of Adjacently Located Phenylalanine Residues in Gel Formation. Soft Matter, 4 (7). pp. 1430-1437.
 
Relation http://dx.doi.org/10.1039/b802205b
http://www.eprints.iicb.res.in/184/