Optically pure β-substituted β-hydroxy aspartates as glutamate transporter blockers

Wehbe, Johny; Kassem, Tarek; Rolland, Valérie; Rolland, Marc; Tabcheh, Mohamad; Roumestant, M. L.; Martinez, Jean

doi:10.1039/b212538b

Cited by 10 publications

(1 citation statement)

References 14 publications

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“…Due to the practical limitations and inefficiencies of reported routes to selected diastereomers of the amino acid 4 , we designed a general strategy to provide all four diastereomers of 4 via a stereoselective dihydroxylation of a cis or trans olefin (cf. 15 ) .…”

mentioning

confidence: 99%

Absolute Configuration and Total Synthesis of a Novel Antimalarial Lipopeptide by the de Novo Preparation of Chiral Nonproteinogenic Amino Acids

et al. 2012

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The absolute configuration (via degradation and Marfey's derivatization studies) and the total synthesis of a novel antimalarial lipid-peptide isolated from Streptomyces sp. (IC(50) = 0.8 μM, Plasmodium falciparum 3D7) is disclosed. To this end, versatile stereocontrolled routes to nonproteinogenic amino acids (via catalytic Mannich, Sharpless methods) and enantiomeric trans fatty acids (via Evans alkylation, Kocienski-Julia olefination) have been developed.

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confidence: 99%

Absolute Configuration and Total Synthesis of a Novel Antimalarial Lipopeptide by the de Novo Preparation of Chiral Nonproteinogenic Amino Acids

et al. 2012

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Methyltrifluoropyruvate

Figueroa¹,

Hsung²,

Li³

et al. 2007

Encyclopedia of Reagents for Organic Synthesis

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Synthesis of Deuterium‐Labelled 3‐Hydroxy‐L‐arginine: Comparative Studies on Different Protecting‐Group Strategies

Lemke

Ducho

2015

Eur J Org Chem

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The β‐hydroxy‐α‐amino acid 3‐hydroxy‐L‐arginine is an important intermediate in biosynthetic pathways involving 2‐oxoglutarate (2‐OG) dependent FeII oxygenases. It also plays an essential role in post‐translational modifications of ribosomal proteins. For profound studies on arginine‐hydroxylating enzymes, synthetic reference compounds are of utmost importance. However, the synthesis of β‐hydroxy‐α‐amino acids is often not trivial. In particular, the preparation of a densely functionalized compound such as 3‐hydroxy‐L‐arginine poses a challenge in terms of a protecting‐group strategy. We have previously established a concise synthesis of 3‐hydroxy‐L‐arginine that is suitable for the preparation of both 3‐epimers of this β‐hydroxy‐α‐amino acid. However, we have since observed a remarkable isomerization reaction upon removal of the hydrogenolytically cleavable protecting groups, thus limiting the reliability of our previously described route. In this paper, we report a comparative study of protecting‐group strategies for this synthetic route, including a newly developed, more robust pathway to the target amino acid. The versatility of this improved route is demonstrated by the synthesis of the deuterium‐labelled derivatives (3R)‐ and (3S)‐3‐hydroxy‐[5‐2H]‐L‐arginine. These new isotope‐labelled arginine derivatives represent important tools for the elucidation of biosynthetic pathways, such as the formation of the arginine‐derived amino acid epicapreomycidine in the biosynthesis of muraymycin nucleoside antibiotics.

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Optically pure β-substituted β-hydroxy aspartates as glutamate transporter blockers

Cited by 10 publications

References 14 publications

Absolute Configuration and Total Synthesis of a Novel Antimalarial Lipopeptide by the de Novo Preparation of Chiral Nonproteinogenic Amino Acids

Absolute Configuration and Total Synthesis of a Novel Antimalarial Lipopeptide by the de Novo Preparation of Chiral Nonproteinogenic Amino Acids

Methyltrifluoropyruvate

Synthesis of Deuterium‐Labelled 3‐Hydroxy‐L‐arginine: Comparative Studies on Different Protecting‐Group Strategies

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