Details
| Original language | English |
|---|---|
| Pages (from-to) | 2442-2445 |
| Number of pages | 4 |
| Journal | CHEMCATCHEM |
| Volume | 7 |
| Issue number | 16 |
| Early online date | 14 Jul 2015 |
| Publication status | Published - 14 Aug 2015 |
| Externally published | Yes |
Abstract
A bi-enzymatic cascade consisting of a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase (ADH) was designed in a convergent fashion to utilise two molar equivalents of cyclohexanone (CHO) and one equivalent of 1,6-hexanediol as a 'double-smart cosubstrate' to produce ε-caprolactone (ECL) with water as sole by-product. The convergent enzymatic cascade reaction reported herein, is performed at ambient conditions in water, is self-sufficient with respect to cofactor, and incorporates all starting materials into the desired product, ECL. Among different enzymes explored, the reaction catalysed by cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 coupled with ADH from Thermoanaerobacter ethanolicus showed the best results, reaching 91 % conversion of CHO after 24 h with a product titre of 2 g L-1. Scale-up of the coupled system (50 mL) performed better than the small-scale reactions and >99 % conversion of CHO and ECL concentration of 20 mM were achieved within 18 h.
Keywords
- alcohol dehydrogenases, Baeyer-Villiger reaction, caprolactone, monooxygenases, multi-enzymatic cascades, smart cosubstrate
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
- Chemistry(all)
- Inorganic Chemistry
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In: CHEMCATCHEM, Vol. 7, No. 16, 14.08.2015, p. 2442-2445.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - A Bi-enzymatic Convergent Cascade for ε-Caprolactone Synthesis Employing 1,6-Hexanediol as a 'Double-Smart Cosubstrate'
AU - Bornadel, Amin
AU - Hatti-Kaul, Rajni
AU - Hollmann, Frank
AU - Kara, Selin
PY - 2015/8/14
Y1 - 2015/8/14
N2 - A bi-enzymatic cascade consisting of a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase (ADH) was designed in a convergent fashion to utilise two molar equivalents of cyclohexanone (CHO) and one equivalent of 1,6-hexanediol as a 'double-smart cosubstrate' to produce ε-caprolactone (ECL) with water as sole by-product. The convergent enzymatic cascade reaction reported herein, is performed at ambient conditions in water, is self-sufficient with respect to cofactor, and incorporates all starting materials into the desired product, ECL. Among different enzymes explored, the reaction catalysed by cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 coupled with ADH from Thermoanaerobacter ethanolicus showed the best results, reaching 91 % conversion of CHO after 24 h with a product titre of 2 g L-1. Scale-up of the coupled system (50 mL) performed better than the small-scale reactions and >99 % conversion of CHO and ECL concentration of 20 mM were achieved within 18 h.
AB - A bi-enzymatic cascade consisting of a Baeyer-Villiger monooxygenase and an alcohol dehydrogenase (ADH) was designed in a convergent fashion to utilise two molar equivalents of cyclohexanone (CHO) and one equivalent of 1,6-hexanediol as a 'double-smart cosubstrate' to produce ε-caprolactone (ECL) with water as sole by-product. The convergent enzymatic cascade reaction reported herein, is performed at ambient conditions in water, is self-sufficient with respect to cofactor, and incorporates all starting materials into the desired product, ECL. Among different enzymes explored, the reaction catalysed by cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 coupled with ADH from Thermoanaerobacter ethanolicus showed the best results, reaching 91 % conversion of CHO after 24 h with a product titre of 2 g L-1. Scale-up of the coupled system (50 mL) performed better than the small-scale reactions and >99 % conversion of CHO and ECL concentration of 20 mM were achieved within 18 h.
KW - alcohol dehydrogenases
KW - Baeyer-Villiger reaction
KW - caprolactone
KW - monooxygenases
KW - multi-enzymatic cascades
KW - smart cosubstrate
UR - http://www.scopus.com/inward/record.url?scp=84939149187&partnerID=8YFLogxK
U2 - 10.1002/cctc.201500511
DO - 10.1002/cctc.201500511
M3 - Article
AN - SCOPUS:84939149187
VL - 7
SP - 2442
EP - 2445
JO - CHEMCATCHEM
JF - CHEMCATCHEM
SN - 1867-3880
IS - 16
ER -