Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation

This work deals with an important strategy of carrying out chemical reactions in biological systems through “orthogonal handles” where two functional groups react with each other selectively without reacting with other potentially reactive functional groups. We have reported the first synthesis of u...

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Main Author: Abbas, Ata
Other Authors: Loh Teck Peng
Format: Theses and Dissertations
Language:English
Published: 2016
Subjects:
Online Access:http://hdl.handle.net/10356/66198
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-661982023-02-28T23:49:00Z Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation Abbas, Ata Loh Teck Peng Xing Bengang School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis This work deals with an important strategy of carrying out chemical reactions in biological systems through “orthogonal handles” where two functional groups react with each other selectively without reacting with other potentially reactive functional groups. We have reported the first synthesis of unsubstituted N-allenamides and their reaction with cysteine thiol in aqueous solution as a means to target cysteine residues in totally unprotected peptides and proteins. Reaction is mild, fast, selective and irreversible, giving products which are stable in human serum. We have demonstrated the application of this strategy in selective labelling of proteins using fluorescent dyes, preparing folate-dye conjugates for imaging of FR positive cancer cell lines and surface modification of silica nanoparticles. We are currently trying to exploit this strategy in preparing some useful conjugates with monoclonal antibodies and some future works are also in pipeline. Doctor of Philosophy (SPMS) 2016-03-15T06:07:31Z 2016-03-15T06:07:31Z 2016 Thesis http://hdl.handle.net/10356/66198 en 151 p. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
spellingShingle DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Abbas, Ata
Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation
description This work deals with an important strategy of carrying out chemical reactions in biological systems through “orthogonal handles” where two functional groups react with each other selectively without reacting with other potentially reactive functional groups. We have reported the first synthesis of unsubstituted N-allenamides and their reaction with cysteine thiol in aqueous solution as a means to target cysteine residues in totally unprotected peptides and proteins. Reaction is mild, fast, selective and irreversible, giving products which are stable in human serum. We have demonstrated the application of this strategy in selective labelling of proteins using fluorescent dyes, preparing folate-dye conjugates for imaging of FR positive cancer cell lines and surface modification of silica nanoparticles. We are currently trying to exploit this strategy in preparing some useful conjugates with monoclonal antibodies and some future works are also in pipeline.
author2 Loh Teck Peng
author_facet Loh Teck Peng
Abbas, Ata
format Theses and Dissertations
author Abbas, Ata
author_sort Abbas, Ata
title Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation
title_short Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation
title_full Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation
title_fullStr Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation
title_full_unstemmed Allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation
title_sort allenamides : synthesis and applications as orthogonal handle for protein modification and bioconjugation
publishDate 2016
url http://hdl.handle.net/10356/66198
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