An 'easy-on, easy-off' protecting group for the enzymatic resolution of (±)-1-phenylethylamine in an aqueous medium

被引:18
作者
Guranda, DT
Khimiuk, AI
van Langen, LM
van Rantwijk, F
Sheldon, RA
Svedas, VK [1 ]
机构
[1] Moscow MV Lomonosov State Univ, Fac Bioengn & Bioinformat, Moscow 119992, Russia
[2] Moscow MV Lomonosov State Univ, Belozersky Inst Physiochem Biol, Moscow 119992, Russia
[3] Delft Univ Technol, Lab Biocatalysis & Organ Chem, NL-2628 BL Delft, Netherlands
基金
俄罗斯基础研究基金会;
关键词
D O I
10.1016/j.tetasy.2004.06.051
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new approach has been developed for the biocatalytic resolution of (+/-)-1-phenylethylamine in 100% aqueous medium based on two integrated enzymatic steps: protection and deprotection of the reactive amine enantiomer catalyzed by the same enzyme-penicillin acylase from Alcaligenes faecalis. An 'easy-on, easy-off' protecting group has been introduced using (R)-phenyl-glycine amide as the acyl donor. (R)-Phenylglycyl-substituted (R)-1-phenylethylamine was poorly soluble and precipitated at enzymatic acylation in an alkaline medium (pH 10-11), driving the synthesis towards high yields. Conversely at pH <7.5, its solubility was continuously increasing, which rendered the subsequent deacylation by the same enzyme highly efficient. In contrast to the resolutions, which employ one biocatalytic step, the new approach made it possible to exploit two sequential enantioselective enzymatic reactions implementing a double enantioselectivity control. Effective enzymatic resolution of (+/-)-1-phenylethylamine in an aqueous medium was performed with (R)-phenyl-glycine amide as an acyl donor using the suggested approach. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2901 / 2906
页数:6
相关论文
共 22 条
  • [1] Kinetic resolution of 1,1′-binaphthylamines via lipase-catalyzed amidation
    Aoyagi, N
    Izumi, T
    [J]. TETRAHEDRON LETTERS, 2002, 43 (32) : 5529 - 5531
  • [2] PEN-G ACYLASE CATALYZED RESOLUTION OF PHENYLACETATE ESTERS OF SECONDARY ALCOHOLS
    BALDARO, E
    DARRIGO, P
    PEDROCCHIFANTONI, G
    ROSELL, CM
    SERVI, S
    TAGLIANI, A
    TERRENI, M
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (05) : 1031 - 1034
  • [3] Optically active amines via lipase-catalyzed methoxyacetylation
    Balkenhohl, F
    Ditrich, K
    Hauer, B
    Ladner, W
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1997, 339 (04): : 381 - 384
  • [4] IMMOBILIZED PENICILLINACYLASE - APPLICATION TO THE SYNTHESIS OF THE DIPEPTIDE ASPARTAME
    FUGANTI, C
    GRASSELLI, P
    CASATI, P
    [J]. TETRAHEDRON LETTERS, 1986, 27 (27) : 3191 - 3194
  • [5] SUBSTRATE-SPECIFICITY AND ENANTIOSELECTIVITY OF PENICILLINACYLASE CATALYZED-HYDROLYSIS OF PHENACETYL ESTERS OF SYNTHETICALLY USEFUL CARBINOLS
    FUGANTI, C
    GRASSELLI, P
    SERVI, S
    LAZZARINI, A
    CASATI, P
    [J]. TETRAHEDRON, 1988, 44 (09) : 2575 - 2582
  • [6] CAL-B-catalyzed resolution of some pharmacologically interesting β-substituted isopropylamines
    González-Sabín, J
    Gotor, V
    Rebolledo, F
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (12) : 1315 - 1320
  • [7] Highly efficient and enantioselective enzymatic acylation of amines in aqueous medium
    Guranda, DT
    van Langen, LM
    van Rantwijk, F
    Sheldon, RA
    Svedas, VK
    [J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (11) : 1645 - 1650
  • [8] ENZYMATIC RESOLUTION OF RACEMIC AMINES IN A CONTINUOUS REACTOR IN ORGANIC-SOLVENTS
    GUTMAN, AL
    MEYER, E
    KALERIN, E
    POLYAK, F
    STERLING, J
    [J]. BIOTECHNOLOGY AND BIOENGINEERING, 1992, 40 (07) : 760 - 767
  • [9] KINETIC RESOLUTION OF P-HYDROXYPHENYL ACETAMIDES BY HYDROLYSIS WITH PEN-G ACYLASE
    GUY, A
    DUMANT, A
    SZIRAKY, P
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) : 1041 - 1044
  • [10] Biotechnological application of Pseudomonas aeruginosa lipase: Efficient kinetic resolution of amines and alcohols
    Jaeger, KE
    Liebeton, K
    Zonta, A
    Schimossek, K
    Reetz, MT
    [J]. APPLIED MICROBIOLOGY AND BIOTECHNOLOGY, 1996, 46 (02) : 99 - 105