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. 2010 Jun 1;15(6):3998-4010.
doi: 10.3390/molecules15063998.

Direct enzymatic route for the preparation of novel enantiomerically enriched hydroxylated beta-amino ester stereoisomers

Eniko Forró  1 , László Schönstein, Loránd Kiss, Alberto Vega-Peñaloza, Eusebio Juaristi, Ferenc Fülöp
Affiliations

Direct enzymatic route for the preparation of novel enantiomerically enriched hydroxylated beta-amino ester stereoisomers

Eniko Forró et al. Molecules. .

Abstract

Enantiomerically enriched hydroxy-substituted beta-amino esters have been synthesized through CAL-B-catalyzed enantioselective hydrolysis in organic media. Moderate to good enantiomeric excess values (ee > or = 52%) were obtained when the CAL-B-catalyzed reactions were performed in t-BuOMe, at 60 degrees C with 0.5 equiv. of added H(2)O as nucleophile.

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Figures

Scheme 1
Scheme 1
Synthesis of (1R*,2S*,5S*)-(±)-4, (1S*,2S*,5S*)-(±)-5 and (1S*,2S*,5S*)-(±)-6.
Scheme 2
Scheme 2
Synthesis of (1S*,2S*,5R*)-(±)-10.
Scheme 3
Scheme 3
Enzymatic hydrolysis of (1S*,2R*,5R*)-(±)-4, (1S*,2S*,5S*)-(±)-5, (1S*,2S*,5S*)-(±)-6 and (1S*,2S*,5R*)-(±)-10.
Figure 1
Figure 1
S-selective hydrolysis of ethyl cis-(2-aminocyclohex-3-ene)-1-carboxylate [28].
Figure 2
Figure 2
S-selective hydrolysis of (1S*,2R*,5R*)-(±)-4.
Figure 3
Figure 3
R-selective hydrolysis of (1S*,2S*,5S*)-(±)-5, (1S*,2S*,5S*)-(±)-6 and (1S*,2S*,5R*)-(±)-10.
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References

    1. Fülöp F. The chemistry of 2-aminocycloalkanecarboxylic acids. Chem. Rev. 2001;101:2181–2204. - PubMed
    1. Kiss L., Forró E., Fülöp F. In: Amino Acids,Peptides and Proteins in Organic Chemistry. Hughes A.B., editor. Vol. 1. Wiley-VCH; Weinheim, Germany: 2009. pp. 367–409.
    1. Zegarac M., Mestrovic E., Hulita N.K., Filic D., Dumic M., Grunenberg A., Keil B., Ceric H. Solid state forms of (-)-(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid. WO 2005100302 A1. PCT Int. Appl. :2005.
    1. Hameršak Z., Roje M., Avdagić A. Quinine-mediated parallel kinetic resolution of racemic cyclic anhydride: Stereoselective synthesis, relative and absolute configuration of novel alicyclic β-amino acids. Tetrahedron Asymmetr. 2007;18:635–644. doi: 10.1016/j.tetasy.2007.02.019. - DOI
    1. Steer D.L., Lew R.A., Perlmutter P., Smith A.I., Aguilar M.I. β-Amino Acids. Versatile peptidomimetics. Curr. Med. Chem. 2002;9:811–822. doi: 10.2174/0929867024606759. - DOI - PubMed

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