Synthesis of enantiopure l-(5-phenylfuran-2-yl)alanines by a sequential multienzyme process

László Csaba Bencze, Balázs Komjáti, Laura Ancuţa Pop, Csaba Paizs, Florin Dan Irimie, József Nagy, L. Poppe, Monica Ioana Toşa

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The enantioselective synthesis of unnatural amino acids is an attractive goal. Increasing attention has been given in recent years to the development of dynamic kinetic resolution processes, providing the desired enantiomer in almost quantitative yields and with high enantiopurity. Herein we describe an efficient sequential multi-enzyme process for the preparation of enantiopure 5-phenylfuran-2-ylalanines l-4a-d, starting from racemic 2-acetamido-3-(5-phenylfuran-2-yl)propanoic acids rac-1a-d. The first step, the CaL-B-mediated dynamic kinetic resolution of the racemic oxazolones provided the N- and C-protected l-amino acids l-2a-d (81-92% ee) with 100% theoretical yield. The protecting groups were removed in excellent yields by a second (mild non-stereoselective PLE mediated hydrolysis of the ester) and a third (Acylase I catalyzed stereoselective hydrolysis of the amide) enzymatic step, thus increasing the enantiomeric excess of the target compounds over 99%.

Original languageEnglish
Article number59353
Pages (from-to)1095-1101
Number of pages7
JournalTetrahedron Asymmetry
Volume26
Issue number18-19
DOIs
Publication statusPublished - Oct 15 2015

Fingerprint

alanine
Alanine
Amino acids
Hydrolysis
Oxazolone
Amino Acids
Kinetics
amino acids
Enantiomers
hydrolysis
Propionates
synthesis
Amides
Esters
Enzymes
enantiomers
kinetics
amides
Acids
enzymes

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Bencze, L. C., Komjáti, B., Pop, L. A., Paizs, C., Irimie, F. D., Nagy, J., ... Toşa, M. I. (2015). Synthesis of enantiopure l-(5-phenylfuran-2-yl)alanines by a sequential multienzyme process. Tetrahedron Asymmetry, 26(18-19), 1095-1101. [59353]. https://doi.org/10.1016/j.tetasy.2015.08.004

Synthesis of enantiopure l-(5-phenylfuran-2-yl)alanines by a sequential multienzyme process. / Bencze, László Csaba; Komjáti, Balázs; Pop, Laura Ancuţa; Paizs, Csaba; Irimie, Florin Dan; Nagy, József; Poppe, L.; Toşa, Monica Ioana.

In: Tetrahedron Asymmetry, Vol. 26, No. 18-19, 59353, 15.10.2015, p. 1095-1101.

Research output: Contribution to journalArticle

Bencze, LC, Komjáti, B, Pop, LA, Paizs, C, Irimie, FD, Nagy, J, Poppe, L & Toşa, MI 2015, 'Synthesis of enantiopure l-(5-phenylfuran-2-yl)alanines by a sequential multienzyme process', Tetrahedron Asymmetry, vol. 26, no. 18-19, 59353, pp. 1095-1101. https://doi.org/10.1016/j.tetasy.2015.08.004
Bencze LC, Komjáti B, Pop LA, Paizs C, Irimie FD, Nagy J et al. Synthesis of enantiopure l-(5-phenylfuran-2-yl)alanines by a sequential multienzyme process. Tetrahedron Asymmetry. 2015 Oct 15;26(18-19):1095-1101. 59353. https://doi.org/10.1016/j.tetasy.2015.08.004
Bencze, László Csaba ; Komjáti, Balázs ; Pop, Laura Ancuţa ; Paizs, Csaba ; Irimie, Florin Dan ; Nagy, József ; Poppe, L. ; Toşa, Monica Ioana. / Synthesis of enantiopure l-(5-phenylfuran-2-yl)alanines by a sequential multienzyme process. In: Tetrahedron Asymmetry. 2015 ; Vol. 26, No. 18-19. pp. 1095-1101.
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