Dataset Information

Synthesis and Characterization of Allyl Terpene Maleate Monomer.

ABSTRACT: Terpenes and their derivatives are sustainable, renewable chemicals that can be used as a complementary hydrocarbon. The exceptions are fossil-based feedstocks and lignin-based feedstocks. A simple method has been found to prepare allyl terpene maleate monomer by substitution reaction at lower reaction temperatures. Using terpenes from turpentine, maleic anhydride and allyl chloride as reactants, the synthesized monomer, terpene-diallyl maleate adduct, was prepared by D-A addition, hydrolysis, and substitution reaction. The resultant monomer was characterized for the first time. The synthesized product will be a versatile monomer and a very important intermediate, having broad application prospects. The synthesized monomer will replace similar aromatic compounds in certain applications because of its low-toxicity and sustainability. The synthesized monomer with two terminal olefin structures has great free radical polymerization potential, according to its physical and chemical properties and exploratory experimentation.

SUBMITTER: Gu Y

PROVIDER: S-EPMC6914792 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Similar Datasets

Project description:N-substituted glycine oligomers, or peptoids, have emerged as an important class of foldamers for the study of biomolecular interactions and for potential use as therapeutic agents. However, the design of peptoids with well-defined conformations a priori remains a formidable challenge. New approaches are required to address this problem, and the systematic study of the role of individual monomer units in the global peptoid folding process represents one strategy. Here, we report our efforts toward this approach through the design, synthesis, and characterization of peptoids containing nitroaromatic monomer units. This work required the synthesis of a new chiral amine building block, (S)-1-(2-nitrophenyl)ethanamine (s2ne), which could be readily installed into peptoids using standard solid-phase peptoid synthesis techniques. We designed a series of peptoid nonamers that allowed us to probe the effects of this relatively electron-deficient and sterically encumbered alpha-chiral side chain on peptoid structure, namely, the peptoid threaded loop and helix. Circular dichroism spectroscopy of the peptoids revealed that the nitroaromatic monomer has a significant effect on peptoid secondary structure. Specifically, the threaded loop structure was disrupted in a nonamer containing alternating N-(S)-1-phenylethylglycine (Nspe) and Ns2ne monomers, and the major conformation was helical instead. Indeed, placement of a single Ns2ne at the N-terminal position of (Nspe)(9) resulted in a destabilized form of the threaded loop structure relative to the homononamer (Nspe)(9). Conversely, we observed that incorporation of N-(S)-1-(4-nitrophenyl)ethylglycine (Nsnp, a p-nitro monomer) at the N-terminal position stabilized the threaded loop structure relative to (Nspe)(9). Additional experiments revealed that nitroaromatic side chains can influence peptoid nonamer folding by modulating the strength of key intramolecular hydrogen bonds in the peptoid threaded loop structure. Steric interactions were also implicated for the Ns2ne monomer. Overall, this study provides further evidence that aromatic side-chain structure, even if perturbed in a single monomer unit, can strongly influence local peptoid backbone conformation.

Dataset Information

Synthesis and Characterization of Allyl Terpene Maleate Monomer.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets