Poly(isoprenecarboxylates) from Glucose via Anhydromevalonolactone

Abstract

A short and efficient synthesis of a series of isoprenecarboxylic acid esters (ICAEs) and their corresponding polymers is presented. The base-catalyzed eliminative ring-opening of anhydromevalonolactone (3) provides isoprenecarboxylic acid (6-H), which was further transformed to the ICAEs. Reversible addition-fragmentation chain-transfer (RAFT) polymerization was used to synthesize high molecular weight (>100 kg mol−1) poly(isoprenecarboxylates) with dispersities (Đ) of ca. 1.5. The glass transition temperatures (Tg) and entanglement molecular weights (Me) of the poly(isoprenecarboxylates) were determined and showed similar trends to the Tg and Me values for analogous poly(acrylate esters). These new glucose-derived materials could provide a sustainable alternative to poly(acrylates).

New antimicrobial compounds produced by Seltsamia galinsogisoli sp. nov., isolated from Galinsoga parviflora as potential inhibitors of FtsZ

“…It also showed four methylene protons at δ H 4.05 (2H, m, H-8), 2.66 (2H, m, H-9), 1.95 (m, 1H, H-15a) and 1.75 (m, 1H, H-15b), five methine protons at 5.85 (1H, s, H-2), 4.83 (1H, m, H-5), 3.6 (1H, m, H-7), 3.6 (1H, m, H-7), 2.92 (1H, brs, H-16); The 13 C NMR spectra (Table 2) indicated the presence of two carbonyl carbons ( δ C 174.3 and 193.0), a pair of olefinic carbons ( δ C 174.3 and 193.0), five methyl carbons ( δ C 22.2*2, 20.7, 13.4 and 8.2), one oxygenated methylene proton carbon ( δ C 58.9), three methylene carbons ( δ C 46.4, 32.4 and 23.5). The 1 H and 13 C NMR spectra of 2 were similar to those of 4-methyl-5,6-dihydro-2H-pyran-2-one except for the absence of two side chains 25,26 . The planar structure of 2 (Fig.…”

Superabsorbent Poly(isoprenecarboxylate) Hydrogels from Glucose

“…The ratio of these competing additions was assessed by 1 H NMR analysis (D 2 O) of the resulting linear poly(ICA-H/Na); the value of 1.0:1.5 was the same as that observed in poly(ICA-R). 23 However, the rate of the polymerization slowed as the percentage of sodium carboxylates in the feed was increased. This phenomenon is also reported for (meth)acrylic acid and sodium (meth)acrylate copolymerizations.…”

“…Recently, we prepared isoprenecarboxylic acid (ICA-H, Figure 1) from anhydromevalonolactone, which can be efficiently obtained from glucose via mevalonate. 23 We proceeded to synthesize and radically polymerize the corresponding isoprenecarboxylate esters (ICA-R) to poly-(isoprenecarboxylic acid esters) [poly(ICA-R)]. We observed that these behave similarly to poly(acrylates) in terms of entanglement molecular weights and glass transition temperatures.…”

Engineering acetyl-CoA supply and ERG9 repression to enhance mevalonate production in Saccharomyces cerevisiae

“…However, fewer studies have focused on the production of mevalonate, a key precursor to isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), the basic building blocks for all isoprenoids and steroids. As a metabolite that can be readily secreted, mevalonate is a promising product itself for the sustainable production of various polymers derived from mevalonolactone, β-methyl-δ-valerolactone, and anhydromevalonolactone (Ball-Jones et al., 2010 ; Dugar & Friedberger, 2015 ; Xiong et al., 2014 ).…”