Show/Hide Menu
Hide/Show Apps
Logout
Türkçe
Türkçe
Search
Search
Login
Login
OpenMETU
OpenMETU
About
About
Open Science Policy
Open Science Policy
Open Access Guideline
Open Access Guideline
Postgraduate Thesis Guideline
Postgraduate Thesis Guideline
Communities & Collections
Communities & Collections
Help
Help
Frequently Asked Questions
Frequently Asked Questions
Guides
Guides
Thesis submission
Thesis submission
MS without thesis term project submission
MS without thesis term project submission
Publication submission with DOI
Publication submission with DOI
Publication submission
Publication submission
Supporting Information
Supporting Information
General Information
General Information
Copyright, Embargo and License
Copyright, Embargo and License
Contact us
Contact us
Fungi mediated conversion of benzil to benzoin and hydrobenzoin
Date
2004-08-23
Author
Demir, AS
Hamamcı, Haluk
Ayhan, P
Duygu, AN
Igdir, AC
Capanoglu, D
Metadata
Show full item record
This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
.
Item Usage Stats
175
views
0
downloads
Cite This
An enzyme system of four fungi catalyses the reduction of benzil to benzoin, as well as benzoin to hydrobenzoin. Depending on the pH of the medium, both enantiomers of benzoin can be obtained in good yield and high ee starting from benzil via a reduction, as well as from rac-benzoin via a novel deracemization reaction. Starting from benzil, (R)-, (S)- and rac-benzoin only (R,R)-hydrobenzoin was obtained in high ee and chemical yield.
Subject Keywords
Ligand
,
Cleavage
,
Auxiliary
,
Convenient
,
Reduction
,
Aryl aldehydes
,
Hydroxy ketones
,
Kinetic resolution
,
Enantioselective synthesis
,
Asymmetric dihydroxylation
URI
https://hdl.handle.net/11511/30834
Journal
TETRAHEDRON-ASYMMETRY
DOI
https://doi.org/10.1016/j.tetasy.2004.07.010
Collections
Graduate School of Natural and Applied Sciences, Article
Suggestions
OpenMETU
Core
Fungi mediated enantioselective biohydrogenation of benzils to benzoins
Demirtaş, Umut; Demir, Ayhan Sıtkı; Department of Biotechnology (2008)
Benzoin is an important a-hydroxy ketone which can be used as chiral intermediate for the synthesis of several drugs. In this study, it was aimed to synthesize this compound by high stereoslectivity and yield by the use of fungal bioconversions. For this purpose, whole cells of four different Fusarium spp. (F. anguoides, F. roseum, F. solanii, F.bulbigenum) were used for reduction of readily available achiral compound benzil. The reaction conditions were optimized as glucose peptone broth consisting of 30g/...
Fungal deracemization of benzoin
Demir, AS; Hamamcı, Haluk; Sesenoglu, O; Neslihanoglu, R; Asikoglu, B; Capanoglu, D (2002-09-02)
An enzyme system of Rhizopus oryzae (ATCC 9363) catalyzes the inversion of the chirality of benzoin via a deracemization reaction and, depending on the pH of the medium, both enantiomers of benzoin are obtained in good yield and high ee starting from rac-benzoin.
Metabolic engineering of aromatic group amino acid pathway in Bacillus subtilis for L-phenylalanine production
Ozcelik, IS; Çalık, Pınar; Calik, G; Ozdamar, TH (Elsevier BV, 2004-11-01)
Metabolic control sites in the aromatic group amino acid pathway (AAAP) of Bacillus subtilis for L-Phenylalanine (Phe) overproduction were determined; and aiming pathway flux amplification, by cloning the flux controlling gene aroH to a multi-copy plasmid, the impact of single gene cloning on pathway flux distributions were investigated. The branch-point metabolites E4P and PEP+E4P supplied in vitro, enhanced Phe production and well defined perturbations were achieved on the AAAP reactions. The intracellula...
Chemoenzymatic synthesis of (1S,2R)-1-amino-2-indanol, a key intermediate of HIV protease inhibitor, indinavir
Demir, AS; Hamamcı, Haluk; Doganel, F; Ozgul, E (2000-04-21)
The synthesis of (1S,2R)-1-amino-2-indanol, a key component of HIV protease inhibitor is accomplished in four steps starting from indanone efficiently and with high levels of diastereo- and enantioselectivity. The starting material is converted into 2-acetoxy-1-indanone involving Manganese (III) acetate oxidation. The 2-acetoxyketone is hydrolyzed to 2-hydroxy-1-indanone enantioselectively using Rhizopus oryzae. Selective reduction of 2-hydroxyoxime derivative, derived from the 2-hydroxyketone, gives the am...
Microorganism mediated stereoselective bio-oxidation and bio-hydrogenation reactions and thiamine pyrophosphate dependent enzyme catalyzed enantioselective acyloin reactions
Sopacı, Şaziye Betül; Demir, Ayhan Sıtkı; Department of Biotechnology (2009)
In this study various microbial and enzymatic methods developed for enantioselective acyloin synthesis for preparation of some pharmaceutically important intermediates. By performing Aspergillus flavus (MAM 200120) mediated biotransformation, enantioselective bio-oxidation of meso-hydrobenzoin was achieved with a high ee value (76%). Racemic form of hydrobenzoin was also employed for the same bio-oxidation process and this bioconversion was resulted in accumulation of meso form (>90% yield) confirming the s...
Citation Formats
IEEE
ACM
APA
CHICAGO
MLA
BibTeX
A. Demir, H. Hamamcı, P. Ayhan, A. Duygu, A. Igdir, and D. Capanoglu, “Fungi mediated conversion of benzil to benzoin and hydrobenzoin,”
TETRAHEDRON-ASYMMETRY
, pp. 2579–2582, 2004, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/30834.