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      Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH

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          Abstract

          We have discovered a simple and versatile reaction condition for oxime mediated bioconjugation reaction that could be adapted for both aldehyde and keto substrates. We found that saline accelerated the oxime kinetics in a concentration-dependent manner under physiological conditions. The reaction mechanism is validated by computational studies, and the versatility of the reaction is demonstrated by cell-surface labeling experiments. Saline offers an efficient and non-toxic catalytic option for performing the bioorthogonal-coupling reaction of biomolecules at the physiological pH. This saline mediated bioconjugation reaction represents the most biofriendly, mild and versatile approach for conjugating sensitive biomolecules and does not require any extensive purification step.

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          Most cited references18

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          Hydrolytic stability of hydrazones and oximes.

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            Nucleophilic catalysis of hydrazone formation and transimination: implications for dynamic covalent chemistry.

            Aniline accelerates hydrazone formation and transimination through nucleophilic catalysis. To demonstrate the method, unprotected peptides are reacted and then scrambled using a hydrazone reaction under conditions relevant for biological applications. The strong enhancement in the rate of hydrazone equilibration broadens the scope of this stable imine in the field of dynamic covalent chemistry.
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              High-efficiency labeling of sialylated glycoproteins on living cells.

              We describe a simple method for efficiently labeling cell-surface sialic acid-containing glycans on living animal cells. The method uses mild periodate oxidation to generate an aldehyde on sialic acids, followed by aniline-catalyzed oxime ligation with a suitable tag. Aniline catalysis dramatically accelerates oxime ligation, allowing use of low concentrations of aminooxy-biotin at neutral pH to label the majority of cell-surface sialylated glycoproteins while maintaining high cell viability.
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                Author and article information

                Contributors
                oommen.varghese@kemi.uu.se
                Journal
                Sci Rep
                Sci Rep
                Scientific Reports
                Nature Publishing Group UK (London )
                2045-2322
                1 February 2018
                1 February 2018
                2018
                : 8
                : 2193
                Affiliations
                [1 ]ISNI 0000 0004 1936 9457, GRID grid.8993.b, Polymer Chemistry Division, Department of Chemistry, Ångström Laboratory, , Uppsala University, Box 538, ; 751 21 Uppsala, Sweden
                [2 ]ISNI 0000 0000 9327 9856, GRID grid.6986.1, Bioengineering and Nanomedicine Lab, Faculty of Biomedical Sciences and Engineering, , Tampere University of Technology, and BioMediTech Institute, ; Tampere, 33720 Finland
                [3 ]ISNI 0000 0004 1936 9457, GRID grid.8993.b, Condensed Matter Theory, Materials Theory Division, Department of Physics and Astronomy, , Ångström Laboratory, Uppsala University, Box 516, ; 751 21 Uppsala, Sweden
                Author information
                http://orcid.org/0000-0002-7256-0758
                http://orcid.org/0000-0003-2768-0133
                http://orcid.org/0000-0002-8242-8005
                http://orcid.org/0000-0001-8872-9928
                Article
                20735
                10.1038/s41598-018-20735-0
                5794741
                29391582
                bf9e8733-985e-421e-8a2b-2f9ffdcc0312
                © The Author(s) 2018

                Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.

                History
                : 29 August 2017
                : 23 January 2018
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