• Je něco špatně v tomto záznamu ?

Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB

J. Gross, Z. Prokop, D. Janssen, K. Faber, M. Hall,

. 2016 ; 17 (15) : 1437-41. [pub] 20160622

Jazyk angličtina Země Německo

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/bmc17023957

The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by the haloalkane dehalogenase LinB from Sphingobium japonicum UT26 proceeds in a sequential fashion: initial formation of intermediate haloalcohols followed by a second hydrolytic step to produce the final diol. Detailed investigation of the course of the reaction revealed favored nucleophilic displacement of the sec-halogen in the first hydrolytic event with pronounced R enantioselectivity. The second hydrolysis step proceeded with a regioselectivity switch at the primary position, with preference for the S enantiomer. Because of complex competition between all eight possible reactions, intermediate haloalcohols formed with moderate to good ee ((S)-4-bromobutan-2-ol: up to 87 %). Similarly, (S)-butane-1,3-diol was formed at a maximum ee of 35 % before full hydrolysis furnished the racemic diol product.

Citace poskytuje Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc17023957
003      
CZ-PrNML
005      
20170906130213.0
007      
ta
008      
170720s2016 gw f 000 0|eng||
009      
AR
024    7_
$a 10.1002/cbic.201600227 $2 doi
035    __
$a (PubMed)27223496
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a gw
100    1_
$a Gross, Johannes $u Department of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, Austria.
245    10
$a Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB / $c J. Gross, Z. Prokop, D. Janssen, K. Faber, M. Hall,
520    9_
$a The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by the haloalkane dehalogenase LinB from Sphingobium japonicum UT26 proceeds in a sequential fashion: initial formation of intermediate haloalcohols followed by a second hydrolytic step to produce the final diol. Detailed investigation of the course of the reaction revealed favored nucleophilic displacement of the sec-halogen in the first hydrolytic event with pronounced R enantioselectivity. The second hydrolysis step proceeded with a regioselectivity switch at the primary position, with preference for the S enantiomer. Because of complex competition between all eight possible reactions, intermediate haloalcohols formed with moderate to good ee ((S)-4-bromobutan-2-ol: up to 87 %). Similarly, (S)-butane-1,3-diol was formed at a maximum ee of 35 % before full hydrolysis furnished the racemic diol product.
650    _2
$a butylenglykoly $x chemická syntéza $7 D002072
650    _2
$a halogenace $7 D054879
650    _2
$a hydrolasy $x metabolismus $7 D006867
650    _2
$a hydrolýza $7 D006868
650    _2
$a Sphingomonadaceae $x enzymologie $7 D042301
650    _2
$a stereoizomerie $7 D013237
650    _2
$a substrátová specifita $7 D013379
655    _2
$a časopisecké články $7 D016428
700    1_
$a Prokop, Zbyněk $u Department Experimental Biology, Faculty of Science, Masaryk University, Kamenice 5A13, 625 00, Brno, Czech Republic.
700    1_
$a Janssen, Dick $u Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, NL.
700    1_
$a Faber, Kurt $u Department of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, Austria.
700    1_
$a Hall, Mélanie $u Department of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, Austria. melanie.hall@uni-graz.at.
773    0_
$w MED00006594 $t Chembiochem a European journal of chemical biology $x 1439-7633 $g Roč. 17, č. 15 (2016), s. 1437-41
856    41
$u https://pubmed.ncbi.nlm.nih.gov/27223496 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y a $z 0
990    __
$a 20170720 $b ABA008
991    __
$a 20170906130812 $b ABA008
999    __
$a ok $b bmc $g 1239638 $s 984870
BAS    __
$a 3
BAS    __
$a PreBMC
BMC    __
$a 2016 $b 17 $c 15 $d 1437-41 $e 20160622 $i 1439-7633 $m Chembiochem $n Chembiochem $x MED00006594
LZP    __
$a Pubmed-20170720

Najít záznam

Citační ukazatele

Možnosti archivace