Synthesis of Novel bis‐Triazolinedione Crosslinked Amphiphilic Polypept(o)ide Nanostructures

Abstract

Owing to their wide range of inherent functionality, hydrolytic stability, biodegradability, and low toxicity, polypeptide‐based materials have been increasingly exploited for controlled drug release applications. More recently, the incorporation of poly(α‐peptoid)s such as poly(sarcosine) into polypeptide‐based materials has been investigated owing to their potential as naturally derived “stealth polymers.” Here the synthesis of novel amphiphilic polypept(o)ide nanoparticles is described utilizing silica templates as a macroinitiator for the ring‐opening copolymerization of l‐tryptophan and d/l‐phenylalanine NCAs and subsequent chain extension with sarcosine NCA. These particles are subsequently crosslinked utilizing the TAD‐indole “click” chemistry and the silica templates are eroded via treatment with HF yielding core crosslinked amphiphilic polypept(o)ide nanostructures. This synthetic strategy offers a unique platform to yield naturally‐derived degradable core‐crosslinked nanostructures, which may have the potential to be utilized in the future as delivery vehicles for hydrophobic small molecules.

Route Development, Antiviral Studies, Field Evaluation and Toxicity of an Antiviral Plant Protectant Nk0238

“…Subsequently, Kricheldorf developed a method involving reactions of N-alkoxy amino acids with SOCl2, PBr3 and other halogenating agents [30] . In addition, phosgene (carbonyl chloride) [31] , diphosgene (trichloromethyl chloride) [32] , triphosgene (bis(trichloromethyl) carbonate) [33] , and di-tertbutyltricarbonate [34] act as cyclocarbonylation reagents for the synthesis of NCAs from unprotected amino acids. We hypothesized that if we selected an appropriate cyclocarbonylation agent, reaction with unprotected L-tryptophan would generate L-trp-NCA, which could then react with n-octylamine to give NK0238 (Fig.…”

Crosslinking of Electrospun Fibres from Unsaturated Polyesters by Bis-Triazolinediones (TAD)

“…As the double bond is preserved in the Alder–ene reaction, further functionalisation can be undertaken utilising the shifted double bond. TADs have been used to modify unsaturated polymers [32], prepare films [33], produce hydrogels [34,35] and produce crosslinked nanostructures [36]. In one example, a bis-functional TAD was applied to unsaturated fatty acids to produce crosslinked films from vegetable oils [37,38].…”