In the light of recent progress in RNA biology, the need for molecules that bind to RNA and thus may be suited to manipulating RNA-mediated processes is steadily increasing. We present a very short and efficient synthetic route to alkynemodified neamine and 2-deoxystreptamine derivatives on a half-gram scale. These derivatives are suitable for constructing a library of potential divalent RNA binders by cop-
C3-Symmetric trimesic acid scaffolds, functionalized with bromoacetyl, aminooxyacetyl and azidoacetyl moieties, respectively, were synthesized and compared regarding their utility for the trivalent presentation of peptides using three different chemoselective ligation reactions, i.e. thioether and oxime formation, as well as the "click" reaction. The latter ligation method was then used to covalently stabilize the trimer of foldon, a 27 amino acid trimerization domain of bacteriophage T4 fibritin, by linking the three foldon monomers to the triazido-functionalized trimesic acid scaffold. This reaction dramatically enhanced the thermal stability of the trimer, while maintaining the correct fold, as demonstrated by CD spectroscopy and X-ray crystal structure analysis, respectively, of the foldon-scaffold conjugates.
The 2-chlorotrityl chloride (2-CTC) resin is one of the most frequently used and most versatile resins for the largescale manufacture of peptides. As a part of our efforts in greening solid-phase peptide synthesis, here, we disclose an efficient procedure for the loading of the first amino acid onto the 2-CTC resin using the green solvent N-butylpyrrolidinone. By applying a design of experiment models, key critical process parameters such as amino acid equivalents and water content were identified. The results obtained suggest that the conditions found can be generalized and applied to any Fmoc-amino acid. Moreover, they serve as a starting point for the optimization of green resin loading.
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