ArticleACS central science2018
PEGylation and Dimerization of Expressed Proteins under Near Equimolar Conditions with Potassium 2-Pyridyl Acyltrifluoroborates.
Article in ACS central science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 74 citations in OpenAlex.
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- An organometallic swap strategy for bottlebrush polymer-protein conjugate synthesis.Chemical communications (Cambridge, England) · 2024Article
- On the origin of the low immunogenicity and biosafety of a neutral α-helical polypeptide as an alternative to polyethylene glycol.Bioactive materials · 2024Article
- Rapid Formation of Non-canonical Phospholipid Membranes by Chemoselective Amide-Forming Ligations with Hydroxylamines.Angewandte Chemie (International ed. in English) · 2024Article
- Chemical synthesis of the EPF-family of plant cysteine-rich proteins and late-stage dye attachment by chemoselective amide-forming ligations.RSC chemical biology · 2022Article
- OrganometallicBioconjugate chemistry · 2022Article
- Chemical and Enzymatic Methods for Post-Translational Protein-Protein Conjugation.Journal of the American Chemical Society · 2022Review
- π-Clamp-Mediated Homo- and Heterodimerization of Single-Domain Antibodies via Site-Specific Homobifunctional Conjugation.Journal of the American Chemical Society · 2022Article
- Site-Specific Cross-Linking of Galectin-1 Homodimers via Poly(ethylene glycol) Bismaleimide.Cellular and molecular bioengineering · 2021Article
- Acrylic boronate: a multifunctional C3 building block for catalytic synthesis of rare organoborons and chemoselective heterobifunctional ligations.Chemical science · 2021Article
- Nanohybrids as Protein-Polymer Conjugate Multimodal Therapeutics.Frontiers in medical technology · 2021Review
- Designed Artificial Protein Heterodimers With Coupled Functions Constructed Using Bio-Orthogonal Chemistry.Frontiers in chemistry · 2021Article
- Deciphering protein post-translational modifications using chemical biology tools.Nature reviews. Chemistry · 2020Review
- Review
- Reversible Click Chemistry for Ultrafast and Quantitative Formation of Protein-Polymer Nanoassembly and Intracellular Protein Delivery.ACS nano · 2019Article
- A modular and concise approach to MIDA acylboronatesChemical science · 2019Article
- Therapeutic Protein PEPylation: The Helix of Nonfouling Synthetic Polypeptides Minimizes Antidrug Antibody Generation.ACS central science · 2019Article
- Facile synthesis of α-aminoboronic acids from amines and potassium acyltrifluoroborates (KATs)Chemical science · 2018Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The covalent conjugation of large, functionalized molecules remains a frontier in synthetic chemistry, as it requires rapid, chemoselective reactions. The potassium acyltrifluoroborate (KAT)-hydroxylamine amide-forming ligation shows promise for conjugations of biomolecules under aqueous, acidic conditions, but the variants reported to date are not suited to ligations at micromolar concentrations. We now report that 2-pyridyl KATs display significantly enhanced ligation kinetics over their aryl counterparts. Following their facile, one-step incorporation onto the termini of polyethylene glycol (PEG) chains, we show that 2-pyridyl KATs can be applied to the construction of protein-polymer conjugates in excellent (>95%) yield. Four distinct expressed, folded proteins equipped with a hydroxylamine could be PEGylated with 2-20 kDa 2-pyridyl mPEG KATs in high yield and with near-equimolar amounts of coupling partners. Furthermore, the use of a bis 2-pyridyl PEG KAT enables the covalent homodimerization of proteins with good conversion. The 2-pyridyl KAT ligation offers an effective alternative to conventional protein-polymer conjugation by operating under aqueous acidic conditions well suited for the handling of folded proteins.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.