Tert-Butoxycarbonyl Protecting Group Location Induces Different Reactive Behaviors in the Five Possible Isoforms of Tri-Boc-Arginine

L-arginine is often used to decorate several scaffolds in order to obtain biomedical devices with increased efficiency and reduced toxicity, so nitrogen atoms need protection for example with BOC group. It has recently been reported that following three protocols which assured the achievement of the widely described (E)-αN,ωN,ω'N-Tri-BOC-arginine as pure isoform, additional four isoforms were obtained. As a rational consequence, further investigations about their reactivity were performed and in this work the results that showed as it is influenced by BOC location, isoforms structure and double bond position and geometry were reported. Only one isoform, i. e. rotamer E, shown appreciable reactivity highlighting that only the procedure which provides it is actually valid. From rotamer E, two new first generation arginine dendrons were prepared. These fragments, exploitable for decorating dendrimer, polymer or lipid scaffolds are very appealing for preparing synthetic arginine materials potentially suitable for biomedical application. Their spectral characterization as well as that of three other unreported isolated compounds were also provided