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Chemoenzymatic Synthesis of a Novel Borneol‐Based Polyester
Author(s) -
Roth Steffen,
Funk Irina,
Hofer Michael,
Sieber Volker
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201701146
Subject(s) - polyester , borneol , chemistry , catalysis , organic chemistry , biotransformation , raw material , terpene , pseudomonas putida , biocatalysis , chemical engineering , enzyme , reaction mechanism , medicine , alternative medicine , pathology , engineering , traditional chinese medicine
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.