Optically Active β-Methyl-δ-Valerolactone: Biosynthesis and Polymerization

Chaoqun Zhang, Deborah K. Schneiderman, Tao Cai, Yi Shu Tai, Kevin Fox, Kechun Zhang

Research output: Contribution to journalArticlepeer-review

10 Scopus citations

Abstract

Chemo-enzymatic pathways were developed to prepare optically enriched (+)-β-methyl-δ-valerolactone and (-)-β-methyl-δ-valerolactone. Anhydromevalonolactone, synthesized by the acid-catalyzed dehydration of bioderived mevalonate, was transformed to (+)-β-methyl-δ-valerolactone with 76% ee and 69% conversion using the mutant enoate reductase, YqjM(C26D, I69T). With the same substrate but a different enoate reductase (OYE2), we obtained the other enantiomer ((-)-β-methyl-δ-valerolactone) with higher selectivity and yield (96% ee and a 92% conversion). The enzyme-docking program LibDock was used to help explain the origin of the divergent enatntioselectivity of the two reductases, and complementary in vitro experiments were used to determine the turnover number and Michaelis constant for each. Finally, the effect of the enantiopurity of the β-methyl-δ-valerolactone monomer on the properties of the corresponding polyester was investigated. Like atactic poly((±)-β-methyl-δ-valerolactone), the isotactic polymer was determined to be amorphous with a low softening temperature (-52 °C).

Original languageEnglish (US)
Pages (from-to)4396-4402
Number of pages7
JournalACS Sustainable Chemistry and Engineering
Volume4
Issue number8
DOIs
StatePublished - Aug 1 2016

Keywords

  • Biosynthesis
  • Chemo-enzymatic pathways
  • Enatntioselectivity
  • Isotactic polymer
  • Thermal properties

Fingerprint Dive into the research topics of 'Optically Active β-Methyl-δ-Valerolactone: Biosynthesis and Polymerization'. Together they form a unique fingerprint.

Cite this