Kyle A Totaro

Publications13
h-index7
Citations129
Highly Influential Citations2
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Systematic Investigation of EDC/sNHS-Mediated Bioconjugation Reactions for Carboxylated Peptide Substrates.
TLDR
Performing bioconjugations on a model affibody protein show that the trends established with model peptides hold for more complex systems, and it is found that biocon jugations are more efficient with high concentrations of amine nucleophile but not sNHS.
Fully automated fast-flow synthesis of antisense phosphorodiamidate morpholino oligomers
TLDR
A fully automated flow-based oligonucleotide synthesizer that reduces coupling times by up to 22-fold compared to previously reported methods and could find broad application not only in designing new SARS-CoV-2 and DMD antisense therapeutics, but also for rapid development of PMO candidates to treat new and emerging diseases.
Rational Design of Selective and Bioactive Inhibitors of the Mycobacterium tuberculosis Proteasome.
TLDR
Selective inhibitors of the Mtb 20S were designed and synthesized on the bases of both its unique substrate preferences and the structures of substrate-mimicking covalent inhibitors of eukaryotic proteasomes called syringolins and do not inhibit the growth of human cell lines in vitro and thus may be starting points for tuberculosis drug development.
Amide-forming chemical ligation via O-acyl hydroxamic acids
TLDR
It is demonstrated that hydroxamic acids—incorporated into the side chain of asparagine or aspartic acid—can be leveraged analogously to form native peptide bonds via an O,N-acyl shift under neutral aqueous conditions.
Efficient and regiospecific syntheses of peptides with piperazic and dehydropiperazic acids via a multicomponent reaction.
TLDR
The reaction's induced intramolecularity can enable the regiospecific formation of products with N2-acyl piperazic acid, which counters the intrinsic and troublesome propensity for p Piperazic acids to react at N1 in acylations.
Use of a Multicomponent Reaction for Chemoselective Derivatization of Multiple Classes of Metabolites
We demonstrate that the Ugi reaction enables chemoselective derivatization of biological amines, carboxylic acids, aldehydes, or ketones with a chromophore under one set of reaction conditions, even…
Macrocyclization of Unprotected Peptide Isocyanates.
TLDR
A chemistry for the facile two-component macrocyclization of unprotected peptide isocyanates of cyclic NYAD-1 analogues was synthesized using the described method and displayed a range of biological activities.
Substrate-guided optimization of the syringolins yields potent proteasome inhibitors with activity against leukemia cell lines.
Automated Fast-Flow Synthesis of Antisense Phosphorodiamidate Morpholino Oligomers
TLDR
A fully automated flow-based oligonucleotide synthesizer that reduces coupling times by 22-fold compared to previously reported batch methods and can be used for on-demand production of a broad range of personalized therapeutic polymers.
A New Ligand for SmI 2
This paper reports the synthesis of a 3-hydroxyprop yl analog of HMPA. This ligand will be coordinated to SmI 2, and kinetic studies are performed. This is worthy of study because the protonation…
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