Amino Acid and Dipeptide Functionalized Polyolefins

Abstract

N-protected amino acid and dipeptide branched, chiral polyolefins have been prepared using acyclic diene metathesis polycondensation chemistry. The polymerizations were performed in THF using Grubbs' second-generation catalyst. The polymers bearing CBz-protected amino acids and dipeptides are semicrystalline with melt transitions of up to 150 °C, whereas the polymers bearing BOC-protected amino acids and dipeptides are primarily amorphous with the exception of the di-BOC-protected lysine polymer, which is semicrystalline.

Bio-olefins via condensation metathesis chemistry

“…We have recently reported the polymerization of various protected amino acid/peptide branched dienes, yielding polyolefins, termed bio-olefins, as further examples of the functional group tolerance of the second generation Grubbs' catalyst 1a [33][34][35][36][37][38][39]. Further, the molecular weights obtained by ADMET polymerizations resemble those obtained by typical polycondensation reactions e.g.…”

“…The pre-monomers were synthesized as previously reported using straight-forward, high yielding reactions as shown in Fig. 3, [37,38].…”

“…To investigate the polymerizability of amino acid branched monomers, the smallest chiral amino acid (alanine) branched dienes were prepared first [33,37,38]. To our delight, all of the alanine branched polymers (9a-9f) were prepared in high molecular weight (Table 1).…”

Multifunctionalization of Dendrimers through Orthogonal Transformations

“…[67][68][69] Another important biological moiety is biotin because of its high-binding affinity for the protein streptavidin. This ligand-receptor interaction is widely used in biosensing, purification, and drug delivery.…”

Polyethylene Prodrugs Using Precisely Placed Pharmaceutical Agents

“…[23,24] This method has proven to be a useful synthetic technique in modeling structure-property relationships in linear low-density polyethylene (LLPE), [25][26][27] and in developing new functionalized materials such as bioolefins. [28][29][30][31][32] In this work three variables were investigated: the choice of drug (ibuprofen or naproxen), the frequency at which this pharmaceutical is attached, and the type of spacer and its linkage between the drug and polyethylene backbone.…”