Rapid chemoenzymatic route to glutamate transporter inhibitor l -TFB-TBOA and related amino acids

Haigen Fu, Sabry H H Younes, Mohammad Saifuddin, Pieter G Tepper, Jielin Zhang, Erik Keller, André Heeres, Wiktor Szymanski, Gerrit J Poelarends

Onderzoeksoutput: ArticleAcademicpeer review

Uittreksel

The complex amino acid (l-threo)-3-[3-[4-(trifluoromethyl)benzoylamino]benzyloxy]aspartate (l-TFB-TBOA) and its derivatives are privileged compounds for studying the roles of excitatory amino acid transporters (EAATs) in regulation of glutamatergic neurotransmission, animal behavior, and in the pathogenesis of neurological diseases. The wide-spread use of l-TFB-TBOA stems from its high potency of EAAT inhibition and the lack of off-target binding to glutamate receptors. However, one of the main challenges in the evaluation of l-TFB-TBOA and its derivatives is the laborious synthesis of these compounds in stereoisomerically pure form. Here, we report an efficient and step-economic chemoenzymatic route that gives access to enantio- and diastereopure l-TFB-TBOA and its derivatives at multigram scale.
Originele taal-2English
Pagina's (van-tot)2341-2344
Aantal pagina's4
TijdschriftOrganic & biomolecular chemistry
Volume15
Nummer van het tijdschrift11
DOI's
StatusPublished - 2017

Vingerafdruk

Amino Acid Transport System X-AG
transporter
glutamates
inhibitors
amino acids
routes
Amino Acid Transport Systems
Amino Acids
Excitatory Amino Acids
Derivatives
aspartates
pathogenesis
stems
Animal Behavior
animals
economics
Glutamate Receptors
Aspartic Acid
Synaptic Transmission
Animals

Citeer dit

Fu, H., Younes, S. H. H., Saifuddin, M., Tepper, P. G., Zhang, J., Keller, E., ... Poelarends, G. J. (2017). Rapid chemoenzymatic route to glutamate transporter inhibitor l -TFB-TBOA and related amino acids. Organic & biomolecular chemistry, 15(11), 2341-2344. https://doi.org/10.1039/c7ob00305f, https://doi.org/10.1039/C7OB00305F
Fu, Haigen ; Younes, Sabry H H ; Saifuddin, Mohammad ; Tepper, Pieter G ; Zhang, Jielin ; Keller, Erik ; Heeres, André ; Szymanski, Wiktor ; Poelarends, Gerrit J. / Rapid chemoenzymatic route to glutamate transporter inhibitor l -TFB-TBOA and related amino acids. In: Organic & biomolecular chemistry. 2017 ; Vol. 15, Nr. 11. blz. 2341-2344.
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abstract = "The complex amino acid (l-threo)-3-[3-[4-(trifluoromethyl)benzoylamino]benzyloxy]aspartate (l-TFB-TBOA) and its derivatives are privileged compounds for studying the roles of excitatory amino acid transporters (EAATs) in regulation of glutamatergic neurotransmission, animal behavior, and in the pathogenesis of neurological diseases. The wide-spread use of l-TFB-TBOA stems from its high potency of EAAT inhibition and the lack of off-target binding to glutamate receptors. However, one of the main challenges in the evaluation of l-TFB-TBOA and its derivatives is the laborious synthesis of these compounds in stereoisomerically pure form. Here, we report an efficient and step-economic chemoenzymatic route that gives access to enantio- and diastereopure l-TFB-TBOA and its derivatives at multigram scale.",
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Fu, H, Younes, SHH, Saifuddin, M, Tepper, PG, Zhang, J, Keller, E, Heeres, A, Szymanski, W & Poelarends, GJ 2017, 'Rapid chemoenzymatic route to glutamate transporter inhibitor l -TFB-TBOA and related amino acids', Organic & biomolecular chemistry, vol. 15, nr. 11, blz. 2341-2344. https://doi.org/10.1039/c7ob00305f, https://doi.org/10.1039/C7OB00305F

Rapid chemoenzymatic route to glutamate transporter inhibitor l -TFB-TBOA and related amino acids. / Fu, Haigen; Younes, Sabry H H; Saifuddin, Mohammad; Tepper, Pieter G; Zhang, Jielin; Keller, Erik; Heeres, André; Szymanski, Wiktor; Poelarends, Gerrit J.

In: Organic & biomolecular chemistry, Vol. 15, Nr. 11, 2017, blz. 2341-2344.

Onderzoeksoutput: ArticleAcademicpeer review

TY - JOUR

T1 - Rapid chemoenzymatic route to glutamate transporter inhibitor l -TFB-TBOA and related amino acids

AU - Fu, Haigen

AU - Younes, Sabry H H

AU - Saifuddin, Mohammad

AU - Tepper, Pieter G

AU - Zhang, Jielin

AU - Keller, Erik

AU - Heeres, André

AU - Szymanski, Wiktor

AU - Poelarends, Gerrit J

PY - 2017

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N2 - The complex amino acid (l-threo)-3-[3-[4-(trifluoromethyl)benzoylamino]benzyloxy]aspartate (l-TFB-TBOA) and its derivatives are privileged compounds for studying the roles of excitatory amino acid transporters (EAATs) in regulation of glutamatergic neurotransmission, animal behavior, and in the pathogenesis of neurological diseases. The wide-spread use of l-TFB-TBOA stems from its high potency of EAAT inhibition and the lack of off-target binding to glutamate receptors. However, one of the main challenges in the evaluation of l-TFB-TBOA and its derivatives is the laborious synthesis of these compounds in stereoisomerically pure form. Here, we report an efficient and step-economic chemoenzymatic route that gives access to enantio- and diastereopure l-TFB-TBOA and its derivatives at multigram scale.

AB - The complex amino acid (l-threo)-3-[3-[4-(trifluoromethyl)benzoylamino]benzyloxy]aspartate (l-TFB-TBOA) and its derivatives are privileged compounds for studying the roles of excitatory amino acid transporters (EAATs) in regulation of glutamatergic neurotransmission, animal behavior, and in the pathogenesis of neurological diseases. The wide-spread use of l-TFB-TBOA stems from its high potency of EAAT inhibition and the lack of off-target binding to glutamate receptors. However, one of the main challenges in the evaluation of l-TFB-TBOA and its derivatives is the laborious synthesis of these compounds in stereoisomerically pure form. Here, we report an efficient and step-economic chemoenzymatic route that gives access to enantio- and diastereopure l-TFB-TBOA and its derivatives at multigram scale.

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KW - amino acids

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