A versatile polypeptoid platform based on N-allyl glycine

Polypeptoid polymers: Synthesis, characterization, and properties

“…[15][16][17][18][19][20] The relative cell viability was found to be dependent on the polymer composition and concentration. It was found that relative cell viability decreases with increasing polymer concentration for all polymers (Figure 13).…”

“…In recent years, the substrate scope for polymerization studies was further expanded to include a variety of R-NCA monomers bearing various N-substituents ( Figure 2). [5,6,[15][16][17][18][19][20][21][22] Luxenhofer et al demonstrated that the polymerizations of Me-NCAs using benzyl amine initiators were shown to proceed in a controlled manner without chain transfer or termination events, producing polysarcosines with narrow Poisson distribution (PDI < 1.1-1.3) and M n s that can be controlled by the initial monomer to initiator feed ratios. [56] The molecular distribution remains narrow (PDI 5 1.01-1.07) even after ten sequential polymerizations of Me-NCA monomers (DP < 100), attesting to the robustness of the living polymerization and suggesting the potential uses of the methods towards the synthesis of well-defined block copolypeptoids via sequential monomer addition.…”

“…reported the postpolymerization functionalization of poly(N-allyl glycine) (PNAlG) [17] and poly(N-propargyl glycine) (PNPgG) via radical thiol-ene chemistry to install different functional moieties (eg, monosaccharide or glycerol) (Scheme 9). [14] MS analysis indicates quantitative modification of PNAlG via thiol-ene addition chemistry.…”

“…The polypeptoid backbone containing tertiary amide linkages is highly polar and hydrophilic. The physicochemical properties of polypeptoids can be tailored by the N-substituent structures, enabling control over the hydrophilicity and lipophilicity balance (HLB), charge characteristics, [13,14] backbone conformation, [1][2][3][4][5][6][7][8][9][10][11][12] solubility, [15][16][17][18][19][20] thermal and crystallization properties of the polypeptoids. [21][22][23][24] Without extensive hydrogen bonding, polypeptoids are thermally processable similar to conventional thermoplastics, [20][21][22][23][24] whereas polypeptides undergo thermal degradation before they can be melt-processed due to the extensive hydrogen bonding interactions.…”

Peptoids for biomaterials science

“…49 Furthermore polyglycerated and polyglycosylated peptoids have been demonstrated by thiol-ene click addition to a NCA polymerized peptoid with allyl sidechains. 50 Peptoid macrocycles with alkyne-terminated sidechains have also been synthesized by both the submonomer protocol 51 and NCA polymerization. 52 Depending on the sequence, the macrocycles could crystallize and adopt two interconvertable conformations and reversibly sequester water.…”