Cross aldol OPAL bioconjugation outcompetes intramolecular hemiaminal cyclisation of proline adjacent N-terminal α-oxo aldehydes at acidic pH-Reference-Cited by-同舟云学术

Cross aldol OPAL bioconjugation outcompetes intramolecular hemiaminal cyclisation of proline adjacent N-terminal α-oxo aldehydes at acidic pH

Published:2024 Issue:6 Volume:14 Page:3723-3729
ISSN:2046-2069
Container-title:RSC Advances
language:en
Short-container-title:RSC Adv.

Author:

Tufail Afzaal¹²,Akkad Saeed¹^ORCID,Hatton Natasha E.¹,Yates Nicholas D. J.¹,Spears Richard J.¹^ORCID,Keenan Tessa¹^ORCID,Parkin Alison¹^ORCID,Signoret Nathalie²,Fascione Martin A.¹^ORCID

Affiliation:

1. Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK

2. Hull York Medical School, University of York, YO10 5DD, UK

Abstract

Bioconjugation at N-terminal α-oxo aldehydes is challenging when proline is adjacent due to competing cyclisation. In this study we show aldol bioconjugations can outcompete this cyclisation at acidic pH in modifications of peptides and proteins.

Funder

UK Research and Innovation

Engineering and Physical Sciences Research Council

University of York

Publisher

Royal Society of Chemistry (RSC)

Link

http://pubs.rsc.org/en/content/articlepdf/2024/RA/D3RA08776J

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