Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates

Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates

Herein, we report use of 2-azidoacrylates to perform site-specific dual functionalization of the cysteine residue of peptides and bovine serum albumin (BSA), a native protein containing one free cysteine residue. The sulfhydryl group of the cysteine residue could be conjugated with 2-azidoacrylates...

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Main Authors: Ariyasu, Shinya, Hayashi, Hirohito, Xing, Bengang, Chiba, Shunsuke
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Peptides and Proteins
Monomers
Online Access:https://hdl.handle.net/10356/154857
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1548572023-02-28T19:35:04Z Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates Ariyasu, Shinya Hayashi, Hirohito Xing, Bengang Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Peptides and Proteins Monomers Herein, we report use of 2-azidoacrylates to perform site-specific dual functionalization of the cysteine residue of peptides and bovine serum albumin (BSA), a native protein containing one free cysteine residue. The sulfhydryl group of the cysteine residue could be conjugated with 2-azidoacrylates bearing various functionalities, such as fluorescent dyes under physiological aqueous buffer conditions, to afford peptide and protein conjugates anchoring an azide moiety. Successive azide-alkyne cycloaddition enables installation of the second functionality, thus affording dual-functionalized peptide- and protein-based materials. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by Nanyang Technological University and Singapore Ministry of Education (Academic Research Fund Tier 2, MOE2013-T2-1-060 to S.C., and Academic Research Fund Tier 1, RG2/15 to S.C., as well as RG11/13 & RG35/15 to B.X.). 2022-01-17T01:29:33Z 2022-01-17T01:29:33Z 2017 Journal Article Ariyasu, S., Hayashi, H., Xing, B. & Chiba, S. (2017). Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates. Bioconjugate Chemistry, 28(4), 897-902. https://dx.doi.org/10.1021/acs.bioconjchem.7b00024 1043-1802 https://hdl.handle.net/10356/154857 10.1021/acs.bioconjchem.7b00024 28212596 2-s2.0-85018522476 4 28 897 902 en RG2/15 MOE2013-T2-1-060 RG11/13 RG35/15 Bioconjugate Chemistry This document is the Accepted Manuscript version of a Published Work that appeared in final form in Bioconjugate Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.bioconjchem.7b00024. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Peptides and Proteins
Monomers
spellingShingle Science::Chemistry
Peptides and Proteins
Monomers
Ariyasu, Shinya
Hayashi, Hirohito
Xing, Bengang
Chiba, Shunsuke
Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates
description Herein, we report use of 2-azidoacrylates to perform site-specific dual functionalization of the cysteine residue of peptides and bovine serum albumin (BSA), a native protein containing one free cysteine residue. The sulfhydryl group of the cysteine residue could be conjugated with 2-azidoacrylates bearing various functionalities, such as fluorescent dyes under physiological aqueous buffer conditions, to afford peptide and protein conjugates anchoring an azide moiety. Successive azide-alkyne cycloaddition enables installation of the second functionality, thus affording dual-functionalized peptide- and protein-based materials.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Ariyasu, Shinya
Hayashi, Hirohito
Xing, Bengang
Chiba, Shunsuke
format Article
author Ariyasu, Shinya
Hayashi, Hirohito
Xing, Bengang
Chiba, Shunsuke
author_sort Ariyasu, Shinya
title Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates
title_short Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates
title_full Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates
title_fullStr Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates
title_full_unstemmed Site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates
title_sort site-specific dual functionalization of cysteine residue in peptides and proteins with 2-azidoacrylates
publishDate 2022
url https://hdl.handle.net/10356/154857
_version_ 1759855501524336640

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