Clickable Tyrosine Binding Bifunctional Linkers for Preparation of DNA–Protein Conjugates

Bauer, Dennis M.; Ahmed, Ishtiaq; Vigovskaya, Antonina; Fruk, Ljiljana

doi:10.1021/bc4001799

Cited by 49 publications

(60 citation statements)

References 39 publications

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“…TAD functionalization was also recently used to radiolabel tyrosine of natural proteins using [18F]4‐(4‐fluorophenyl)‐1,2,4‐triazole‐3,5‐dione . In another example, Bauer et al prepared bifunctional TAD linkers and showed protein–DNA conjugation …”

Section: Introductionmentioning

confidence: 99%

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Hanay

Ritzen

Brougham

et al. 2017

Macromolecular Bioscience

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Highly efficient functionalization and cross-linking of polypeptides is achieved via tyrosine-triazolinedione (TAD) conjugation chemistry. The feasibility of the reaction is demonstrated by the reaction of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with tyrosine containing block copolymer poly(ethylene glycol)-Tyr as well as a statistical copolymer of tyrosine and lysine (poly(Lys -st-Tyr )) prepared form N-carboxyanhydride polymerization. Selective reaction of PTAD with the tyrosine units is obtained and verified by size exclusion chromatography and NMR spectroscopy. Moreover, two monofunctional and two difunctional TAD molecules are synthesized. It is found that their stability in the aqueous reaction media significantly varied. Under optimized reaction conditions selective functionalization and cross-linking, yielding polypeptide hydrogels, can be achieved. TAD-mediated conjugation can offer an interesting addition in the toolbox of selective (click-like) polypeptide conjugation methodologies as it does not require functional non-natural amino acids.

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Section: Introductionmentioning

confidence: 99%

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Hanay

Ritzen

Brougham

et al. 2017

Macromolecular Bioscience

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“…20,21 Intrigued by these results, we studied D1 modication with cyclic diazodicarboxamides 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD) in mixed organic/aqueous media (Scheme 3). 22 Therefore, it is expected to construct advanced biomaterials with tyrosine-conjugated biodynamer as the building block through the tyrosine-click reaction. of PTAD for 24 h. Aer purication by dialysis, 1 H NMR analysis revealed the presence of the signals of acylhydrazone proton (CH]NNH) and aromatic -OH, and the appearance of signals at d 11.3, 7.42, 7.25 ppm corresponding to the modied PTAD moiety (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…9 Tyrosine residues have unique reactivity because of the acidic proton of the phenol ring. [20][21][22] Intrigued by the possibility of using ideas from the protein modication through tyrosine, we sought to introduce tyrosine moiety into the polymer to create a facile bioconjugation strategy for the synthetic polymers through tyrosine. Under acidic conditions, an ene-like reaction occurs at a carbon atom on the aromatic ring.…”

Section: Introductionmentioning

confidence: 99%

Environmentally responsive amino acid-bioconjugated dynamic covalent copolymer as a versatile scaffold for conjugation

Wang

Liu

et al. 2015

RSC Adv.

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Biodynamers display the properties of biomolecules with the adaptive nature of dynamic covalent polymers and have great potential as "smart" materials. The bioconjugation of L-tyrosine hydrazide to the end of bisaldehyde-functionalized thermoresponsive copolymer chains via reversible acylhydrazone linkage generated a biodynamer with thermo/pH-responsive and adaptive features. Because of the introduction of amino acid end groups, the biodynamer had an isoelectric point (IEP) at pH 4.70 and possessed a pHdependent LCST. The properties of the biodynamer were tunable through chain exchange reactions with other hydrazine or hydrazide molecules. The biodynamer endowed biological recognition by exchange with biotin hydrazide. The complex formed by the biotinylated dynamer and streptavidin demonstrated pH-responsive features. Because of the versatile reactivity of the phenolic moiety, this biodynamer provided a reactive scaffold for further modification. The cyclic diazodicarboxamide was attached to the biodynamer through the tyrosine-click reaction. Protein bioconjugate with pH-responsive and adaptive features was prepared via HRP-catalyzed coupling reaction.

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“…This makes engineering a single, non‐perturbative reactive site in a protein of interest relatively straightforward . The use of diazocarboxamides for tyrosine‐phenol targeting has also been reported as an efficient means to conjugate DNA to proteins (Figure c); however, this approach has not been widely adopted, likely because it still requires the user to synthesize diazocarboxamide‐containing heterobifunctional linkers . Another promising strategy for targeting a single site in proteins is N‐terminal (α‐amine) protein labeling via 2‐pyridinecarboxyaldehydes as initially reported by the Francis lab .…”

Section: Bioorthogonal Chemistry For Dna Barcoding Of Proteins and Otmentioning

confidence: 99%

Nucleic Acid‐Barcoding Technologies: Converting DNA Sequencing into a Broad‐Spectrum Molecular Counter

Liszczak

Muir

2019

Angew Chem Int Ed

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The emergence of high-throughput DNA sequencing technologies sparked an immediate revolution in the field of genomics that has rippled into many branches of the life and physical sciences. The remarkable sensitivity, specificity, throughput, and multiplexing capacity that are inherent to massively parallel DNA sequencing have since motivated its use as a broad-spectrum molecular counter in small molecule and peptide-based inhibitor discovery, high-throughput biochemistry, protein and cellular detection and diagnostics, and even materials science. A key aspect of extrapolating DNA sequencing to 'non-traditional' applications is the underlying need to append nucleic acid barcodes to entities of interest. In this review, we describe the chemical and biochemical approaches that have enabled facile nucleic acid barcoding of proteinaceous and non-proteinaceous materials, and provide exciting examples of downstream technologies that have been made possible by DNA-encoded molecules. Considering that commercially available high-throughput sequencers were first released less than 15 years ago, we believe related applications will continue to mature for years to come, and close by proposing potential new frontiers to support this assertion.

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Clickable Tyrosine Binding Bifunctional Linkers for Preparation of DNA–Protein Conjugates

Cited by 49 publications

References 39 publications

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Exploring Tyrosine‐Triazolinedione (TAD) Reactions for the Selective Conjugation and Cross‐Linking of N‐Carboxyanhydride (NCA) Derived Synthetic Copolypeptides

Environmentally responsive amino acid-bioconjugated dynamic covalent copolymer as a versatile scaffold for conjugation

Nucleic Acid‐Barcoding Technologies: Converting DNA Sequencing into a Broad‐Spectrum Molecular Counter

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