Chemoenzymatic Synthesis of a Novel Borneol‐Based Polyester. Issue 18 (24th August 2017)

• Record Type: Journal Article
• Authors: Roth, Steffen; Funk, Irina; Hofer, Michael; Sieber, Volker
• Is Part Of: ChemSusChem. Volume 10:Issue 18(2017)
• Page Start: 3574
• Page End: 3580
• Publication Date: 2017-08-24
• Subjects: biocatalysis -- biotransformations -- copolymerization -- polymers -- terpenoids; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.201701146
• Languages: English
• ISSNs: 1864-5631

Abstract

Abstract: Terpenes are a class of natural compounds that have recently moved into the focus as a bio‐based resource for chemical production, owing to their abundance, their mostly cyclic structures, and the presence of olefin or single hydroxy groups. To apply this raw material in new industrial fields, a second hydroxy group is inserted into borneol by cytochrome P450cam (CYP101) enzymes in a whole‐cell catalytic biotransformation with Pseudomonas putida KT2440. Next, a semi‐continuous batch system was developed to produce 5‐ exo ‐hydroxyborneol with a final concentration of 0.54 g L −1 . The bifunctional terpene was then used for the synthesis of a bio‐based polyester by a solvent‐free polycondensation reaction. The resulting polymer showed a glass transition temperature of around 70 °C and a molecular weight in the range of 2000–4000 g mol −1 ( M w ). These results show that whole‐cell catalytic biotransformation of terpenes could lead to bio‐based, higher‐functionalized monomers, which might be basic raw materials for different fields of application, such as biopolymers. Abstract : The borneol supremacy : A new monomer for terpene‐based biopolymers is produced by whole‐cell biotransformation. Pseudomonas putida KT2440 is used as a host for the hydroxylation of (−)‐borneol by P450cam enzymes. A semi‐continuous batch system was developed to yield 5‐ exo ‐hydroxyborneol in a final concentration of 0.54 g L −1 . The purified product is then used to create novel terpene‐based polyesters.