Cargando…

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

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 me...

Descripción completa

Detalles Bibliográficos
Autores principales: Wang, Shujiang, Nawale, Ganesh N., Kadekar, Sandeep, Oommen, Oommen P., Jena, Naresh K., Chakraborty, Sudip, Hilborn, Jöns, Varghese, Oommen P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5794741/
https://www.ncbi.nlm.nih.gov/pubmed/29391582
http://dx.doi.org/10.1038/s41598-018-20735-0
_version_ 1783297153823670272
author Wang, Shujiang
Nawale, Ganesh N.
Kadekar, Sandeep
Oommen, Oommen P.
Jena, Naresh K.
Chakraborty, Sudip
Hilborn, Jöns
Varghese, Oommen P.
author_facet Wang, Shujiang
Nawale, Ganesh N.
Kadekar, Sandeep
Oommen, Oommen P.
Jena, Naresh K.
Chakraborty, Sudip
Hilborn, Jöns
Varghese, Oommen P.
author_sort Wang, Shujiang
collection PubMed
description 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.
format Online
Article
Text
id pubmed-5794741
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-57947412018-02-12 Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH Wang, Shujiang Nawale, Ganesh N. Kadekar, Sandeep Oommen, Oommen P. Jena, Naresh K. Chakraborty, Sudip Hilborn, Jöns Varghese, Oommen P. Sci Rep Article 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. Nature Publishing Group UK 2018-02-01 /pmc/articles/PMC5794741/ /pubmed/29391582 http://dx.doi.org/10.1038/s41598-018-20735-0 Text en © 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/.
spellingShingle Article
Wang, Shujiang
Nawale, Ganesh N.
Kadekar, Sandeep
Oommen, Oommen P.
Jena, Naresh K.
Chakraborty, Sudip
Hilborn, Jöns
Varghese, Oommen P.
Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH
title Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH
title_full Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH
title_fullStr Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH
title_full_unstemmed Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH
title_short Saline Accelerates Oxime Reaction with Aldehyde and Keto Substrates at Physiological pH
title_sort saline accelerates oxime reaction with aldehyde and keto substrates at physiological ph
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5794741/
https://www.ncbi.nlm.nih.gov/pubmed/29391582
http://dx.doi.org/10.1038/s41598-018-20735-0
work_keys_str_mv AT wangshujiang salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph
AT nawaleganeshn salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph
AT kadekarsandeep salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph
AT oommenoommenp salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph
AT jenanareshk salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph
AT chakrabortysudip salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph
AT hilbornjons salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph
AT vargheseoommenp salineacceleratesoximereactionwithaldehydeandketosubstratesatphysiologicalph