Synthesis of new optically pure tetrabromobenzotriazole derivatives via lipase-catalyzed transesterification

Adam M. Wawro , Monika Wielechowska , Maria Bretner

Abstract

An efficient and convenient approach to synthesis of new, enantiopure hydroxyalkyl derivatives of 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt) has been developed. Prochiral ketones synthesized through alkylation of TBBt were reduced to racemic secondary alcohols, which were separated by kinetic resolution carried out by lipase-catalyzed transesterification. After optimization of solvent, lipase and acyl donor group, the highest enantioselectivity factor (E \> 200) and optical purity of the products (\>99\%) was achieved with lipase Amano AK from Pseudomonas fluorescens in tert-butyl methyl ether.
Author Adam M. Wawro (FC / IBC / DDTB)
Adam M. Wawro,,
- Department Of Drug Technology And Biotechnology
, Monika Wielechowska (FC / IBC / DDTB)
Monika Wielechowska,,
- Department Of Drug Technology And Biotechnology
, Maria Bretner (FC / IBC / DDTB)
Maria Bretner,,
- Department Of Drug Technology And Biotechnology
Journal seriesJournal of Molecular Catalysis B-Enzymatic, ISSN 1381-1177
Issue year2013
Vol87
Pages44-50
Publication size in sheets0.5
Keywords in EnglishEnzymatic transesterification, Inhibitors of casein kinase CK2, Lipase, Tetrabromobenzotriazole derivatives
ASJC Classification1508 Process Chemistry and Technology; 1303 Biochemistry; 1502 Bioengineering; 1503 Catalysis
DOIDOI:10.1016/j.molcatb.2012.10.013
URL http://www.sciencedirect.com/science/article/pii/S1381117712002810
Languageen angielski
File
Journal of Molecular Catalysis B.pdf 628.5 KB
Score (nominal)30
Score sourcejournalList
ScoreMinisterial score = 30.0, 17-08-2020, ArticleFromJournal
Ministerial score (2013-2016) = 30.0, 17-08-2020, ArticleFromJournal
Publication indicators Scopus Citations = 7; WoS Citations = 5; GS Citations = 3.0; Scopus SNIP (Source Normalised Impact per Paper): 2013 = 1.378; WoS Impact Factor: 2013 = 2.745 (2) - 2013=2.786 (5)
Citation count*3 (2015-10-29)
Cite
Share Share

Get link to the record


* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.
Back
Confirmation
Are you sure?