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

被引：9
|
作者：
Bálint, J
Kiss, V
Egri, G
Kálai, T
Demeter, A
Balog, M
Fogassy, E
Hideg, K
机构：
[1] Univ Pecs, Inst Organ & Med Chem, H-7602 Pecs, Hungary
[2] Tech Univ Budapest, Dept Organ Chem Technol, H-1521 Budapest, Hungary
[3] Gedeon Richter Chem Works Ltd, Spectroscop Res Div, H-1475 Budapest, Hungary
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 04期
基金：
匈牙利科学研究基金会;
关键词：
D O I：
10.1016/j.tetasy.2003.12.026
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
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 F-19 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. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：671 / 679
页数：9
相关论文
共 50 条
  • [21] Kinetic resolution of 2-chloro-1-(3,4-dichlorophenyl)ethanol by lipase-catalyzed transesterification
    Wang Ming-Hui
    Li Ya-Feng
    Liu Yong-Jun
    Zhang Shu-Sheng
    CHINESE JOURNAL OF CHEMISTRY, 2007, 25 (11) : 1700 - 1703
  • [22] Lipase-catalyzed kinetic resolution of 3-phenyloxazolidin-2-one derivatives: Cascade O- and N-alkoxycarbonylations
    Zhang, Yang
    Zhang, Yang
    Xie, Sheng
    Yan, Mingdi
    Ramstrom, Olof
    CATALYSIS COMMUNICATIONS, 2016, 82 : 11 - 15
  • [23] Lipase-Catalyzed Kinetic Resolution of (±)-1-(2-Furyl) Ethanol in Nonaqueous Media
    Devendran, Saravanan
    Yadav, Ganapati D.
    CHIRALITY, 2014, 26 (06) : 286 - 292
  • [24] 1-alkylthio-3-aryloxypropan-2-ols: synthesis and enantiomer separation by lipase-catalyzed transesterification
    Wielechowska, M
    Plenkiewicz, J
    TETRAHEDRON-ASYMMETRY, 2003, 14 (20) : 3203 - 3210
  • [25] Chemoenzymatic synthesis of duloxetine and its enantiomer: Lipase-catalyzed resolution of 3-hydroxy-3-(2-thienyl) propanenitrile
    Kamal, A
    Khanna, GBR
    Ramu, R
    Krishnaji, T
    TETRAHEDRON LETTERS, 2003, 44 (25) : 4783 - 4787
  • [26] Pharmacokinetic study of acyl-protected hydroxylamine probe, 1-acetoxy-3-carbamoyl-2,2,5,5-tetramethylpyrrolidine, for in vivo measurements of reactive oxygen species
    Saito, K
    Takeshita, K
    Anzai, K
    Ozawa, T
    FREE RADICAL BIOLOGY AND MEDICINE, 2004, 36 (04) : 517 - 525
  • [27] First synthesis of (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) by lipase-catalyzed kinetic resolution
    Mase, N
    Nishi, T
    Takamori, Y
    Yoda, H
    Takabe, K
    TETRAHEDRON-ASYMMETRY, 1999, 10 (23) : 4469 - 4471
  • [28] Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (-)-disparlure
    Tsuboi, S
    Yamafuji, N
    Utaka, M
    TETRAHEDRON-ASYMMETRY, 1997, 8 (03) : 375 - 379
  • [29] Lipase-catalyzed kinetic resolution of the racemic mixtures of 1-aryloxy-3-nitrato- and 1-aryloxy-3-azido-2-propanols
    Pchelka, B
    Radomska, J
    Plenkiewicz, J
    SYNTHETIC COMMUNICATIONS, 1998, 28 (23) : 4355 - 4364
  • [30] NITROXYLS .6. SYNTHESIS AND REACTIONS OF 3-HYDROXYMETHYL-2,2,5,5-TETRAMETHYL-2,5-DIHYDROPYRROLE-1-OXYL AND 3-FORMYL DERIVATIVES
    HIDEG, K
    HANKOVSZKY, HO
    LEX, L
    KULCSAR, G
    SYNTHESIS-STUTTGART, 1980, (11): : 911 - 914
12345