Kinetic resolution of 1-oxyl-3-hydroxymethyl-2,2,5,5-tetramethylpyrrolidine derivatives by lipase-catalyzed enantiomer selective acylation

Graphic Three chiral stable free radicals containing a hydroxymethyl group have been resolved by biocatalysis. By recrystallization and/or re-esterification each molecule was produced in very high enantiomeric purity. The resolved 1-oxyl-3-hydroxymethyl-2,2,5,5-tetramethylpyrrolidine alcohols were c...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron: asymmetry Vol. 15; no. 4; pp. 671 - 679
Main Authors Bálint, József, Kiss, Violetta, Egri, Gabriella, Kálai, Tamás, Demeter, Ádám, Balog, Mária, Fogassy, Elemér, Hideg, Kálmán
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.02.2004
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
SIDE-CHAIN STRUCTURE
NITROXIDE
MOTION
SPIN-LABEL REAGENTS
ABSOLUTE-CONFIGURATION
PROTEINS
Online AccessGet full text

Cover

More Information
Summary:Graphic Three chiral stable free radicals containing a hydroxymethyl group have been resolved by biocatalysis. By recrystallization and/or re-esterification each molecule was produced in very high enantiomeric purity. The resolved 1-oxyl-3-hydroxymethyl-2,2,5,5-tetramethylpyrrolidine alcohols were converted to methanethiosulfonate spin labels, 1-oxyl-3-methanesulfonylthiomethyl-2,2,5,5-tetramethylpyrrolidines. Enantiomeric purities have been determined by the 19F NMR method of the respective Mosher esters. Absolute configurations were assigned by comparing the chemical shifts of the Mosher esters and also by comparing the specific rotations obtained with the same enzyme preparations.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2003.12.026