We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Stereoselective yeast-mediated reduction of trans-5-(1′-oxo-3′-methylbutyl)-3-methyldihydrofuran-2-one: production of chiral intermediates for the synthesis of β-secretase inhibitors.
- Authors
Gładkowski, Witold; Mituła, Paweł
- Abstract
Objective: To investigate the usefulness of yeast strains to the production of chiral hydroxylactones, important synthons in the synthesis of β-secretase inhibitors. Results: Strains Rhodotorula glutinis KCh 242, Rhodotorula rubra KCh 82, Rhodotorula marina KCh 77 and Saccharomyces cerevisiae KCh 464 reduced racemic trans-5-(1′-oxo-3′-methylbutyl)-3-methyldihydrofuran-2-one ( 4) according to the Prelog's rule to afford preferentially the stereoisomers with S configurations at C-1′. R. marina KCh 77 and R. glutinis KCh 242 exhibited selectivity towards 3 S, 5 R enantiomer of the substrate, whereas R. rubra KCh 82 and S. cerevisiae KCh 464 preferred the reduction of its antipode. The highest yield of 3 R,5 S,1′ S-hydroxylactone 3c (78 %) was obtained with R. rubra KCh 82. Conclusions: Different stereoisomers of trans-5-(1′-hydroxy-3′-methylbutyl)-3-methyldihydrofuran-2-one and its 5-substituted analogues are produced as important intermediates in the synthesis of drugs for the therapy of Alzheimer's disease.
- Subjects
STEREOSELECTIVE reactions; DIHYDROFURANS; CHIRALITY; SECRETASE inhibitors; INTERMEDIATES (Chemistry); BIOSYNTHESIS
- Publication
Biotechnology Letters, 2016, Vol 38, Issue 1, p103
- ISSN
0141-5492
- Publication type
Article
- DOI
10.1007/s10529-015-1954-6