Deamidation of pseudopeptidic molecular hydrogelators and its application to controlled release
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comunitat-uji-handle3:10234/107363
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Title
Deamidation of pseudopeptidic molecular hydrogelators and its application to controlled releaseAuthor (s)
Tutor/Supervisor; University.Department
Miravet Celades, Juan Felipe; Angulo Pachón, César Augusto; Universitat Jaume I. Departament de Química Inorgànica i OrgànicaDate
2017Publisher
Universitat Jaume IAbstract
Hypothesis: The incorporation of a succinic acid-derived moiety in amino acid derivatives would favor an
intramolecular catalysis of a deamidation reaction. Such reaction would permit controlled disassembly of
mol ... [+]
Hypothesis: The incorporation of a succinic acid-derived moiety in amino acid derivatives would favor an
intramolecular catalysis of a deamidation reaction. Such reaction would permit controlled disassembly of
molecular hydrogelators and the use of the hydrogels for controlled release of actives.
Experimental: Low molecular weight hydrogelators containing a succinic acid-derived moiety were prepared
by conventional organic synthesis procedures. Hydrogels were examined by electron microscopy
and 1
H NMR studies were carried out to evaluate the solubility in water of the hydrogelators and the
deamidation reaction. Liberation of Rose Bengal entrapped in the hydrogels was monitored by UV–Vis
spectroscopy.
Findings: Molecular hydrogels formed by pseudopeptidic derivatives of L-valine suffer a thermal deamidation
reaction, leading to partial disassembly. The succinic acid-derived moiety present in the gelators is
responsible of intramolecular catalysis of a deamidation reaction. Such neighboring group effect is reminiscent
of biochemical processes such as protein deamidation and self-excision of inteins. It has been
found that the thermodynamic equilibrium of the deamidation reaction is regulated by the efficiency
of hydrogelation. As a proof of concept, the thermally promoted deamidation is applied to controlled
release of Rose Bengal. [-]
Subject
Description
Treball Final de Màster Universitari en Química Aplicada i Farmacològica. Codi: SIM138. Curs acadèmic: 2016/2017
Type
info:eu-repo/semantics/masterThesisRights
Licencia CC-BY-NC-SA
info:eu-repo/semantics/openAccess
info:eu-repo/semantics/openAccess
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