Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 10, Pages 1618-1624Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201501066
Keywords
alcohol dehydrogenases; atom economy; biocatalysis; cofactor recycling; transaminases
Categories
Funding
- MICINN [CTQ2013-44153-P]
- Principado de Asturias [FC-15-GRUPIN14-002]
- Principado de Asturias
Ask authors/readers for more resources
Both cis- and trans-but-2-ene-1,4-diamines have been prepared and efficiently applied as sacrificial cosubstrates in enzymatic transamination reactions. The best results were obtained with the cis-diamine. The thermodynamic equilibrium of the stereoselective transamination process is shifted to the amine formation due to tautomerization of 5H-pyrrole into 1H-pyrrole, achieving high conversions (78-99%) and enantiomeric excess (up to >99%) by using a small excess of the amine donor. Furthermore, when the reaction proceeded, a strong coloration was observed due to polymerization of 1H-pyrrole. A structurally related compound, cis-but-2-ene-1,4-diol, has been utilized as cosubstrate in different alcohol dehydrogenase (ADH)-mediated bioreductions. In this case, high conversions (91-99%) were observed due to a lactonization process. Both strategies are convenient from both synthetic and atom economy points of view in the production of valuable optically active products.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available