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

J 2016

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

GROSS, J.; Zbyněk PROKOP; D. JANSSEN; Kurt FABER; M. HALL et al.

Základní údaje

Originální název

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

Autoři

GROSS, J.; Zbyněk PROKOP; D. JANSSEN; Kurt FABER a M. HALL

Vydání

CHEMBIOCHEM, WILEY-V C H VERLAG GMBH, 2016, 1439-4227

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10600 1.6 Biological sciences

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 2.847

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/16:00088568

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

biocatalysis; enantioselectivity; haloalkane dehalogenase; hydrolysis; LinB; regioselectivity

Štítky

AKR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 8. 4. 2020 14:01, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by haloalkane dehalogenase LinB fromSphingobium japonicum UT26 proceeds in a sequential fashion via 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. Due to complex competition between all eight possible pathways, intermediate haloalcohols could be formed with moderate to good ee values [(S)-4-bromobutan-2-ol in up to 87% ee]. Similarly, (S)-1,3-butanediol was formed in max. ee 35% before full hydrolysis furnished the racemic diol product.

Návaznosti

ED2.1.00/19.0382, projekt VaV

Název: CETOCOEN UPgrade

GA16-07965S, projekt VaV

Název: Řízená evoluce dynamických elementů v enzymech s využitím mikrofluidních čipů

Investor: Grantová agentura ČR, Řízená evoluce dynamických elementů v enzymech s využitím mikrofluidních čipů

LO1214, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Centrum pro výzkum toxických látek v prostředí

Citovat

GROSS, J.; Zbyněk PROKOP; D. JANSSEN; Kurt FABER a M. HALL. Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB. CHEMBIOCHEM. WILEY-V C H VERLAG GMBH, 2016, roč. 17, č. 15, s. 1437-1441. ISSN 1439-4227. Dostupné z: https://doi.org/10.1002/cbic.201600227.

@article{1368405,
   author = {Gross, J. and Prokop, Zbyněk and Janssen, D. and Faber, Kurt and Hall, M.},
   article_number = {15},
   doi = {https://doi.org/10.1002/cbic.201600227},
   keywords = {biocatalysis; enantioselectivity; haloalkane dehalogenase; hydrolysis; LinB; regioselectivity},
   language = {eng},
   issn = {1439-4227},
   journal = {CHEMBIOCHEM},
   title = {Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB},
   url = {http://dx.doi.org/10.1002/cbic.201600227},
   volume = {17},
   year = {2016}
}

TY  - JOUR
ID  - 1368405
AU  - Gross, J. - Prokop, Zbyněk - Janssen, D. - Faber, Kurt - Hall, M.
PY  - 2016
TI  - Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB
JF  - CHEMBIOCHEM
VL  - 17
IS  - 15
SP  - 1437-1441
EP  - 1437-1441
PB  - WILEY-V C H VERLAG GMBH
SN  - 14394227
KW  - biocatalysis
KW  - enantioselectivity
KW  - haloalkane dehalogenase
KW  - hydrolysis
KW  - LinB
KW  - regioselectivity
UR  - http://dx.doi.org/10.1002/cbic.201600227
L2  - http://dx.doi.org/10.1002/cbic.201600227
N2  - The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by haloalkane dehalogenase LinB fromSphingobium japonicum UT26 proceeds in a sequential fashion via 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. Due to complex competition between all eight possible pathways, intermediate haloalcohols could be formed with moderate to good ee values [(S)-4-bromobutan-2-ol in up to 87% ee]. Similarly, (S)-1,3-butanediol was formed in max. ee 35% before full hydrolysis furnished the racemic diol product.
ER  -

GROSS, J.; Zbyněk PROKOP; D. JANSSEN; Kurt FABER a M. HALL. Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB. \textit{CHEMBIOCHEM}. WILEY-V C H VERLAG GMBH, 2016, roč.~17, č.~15, s.~1437-1441. ISSN~1439-4227. Dostupné z: https://doi.org/10.1002/cbic.201600227.

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