An Efficient Chemoenzymatic Approach to (<i>S</i>)-γ-Fluoroleucine Ethyl Ester

Limanto, John; Shafiee, Ali; Devine, Paul N.; Upadhyay, Veena; Desmond, Richard; Foster, Bruce R.; Gauthier, Donald R.; Reamer, Robert A.; Volante, R. P.

doi:10.1021/jo047918j

Cited by 41 publications

(26 citation statements)

References 15 publications

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“…Lipases may also be useful in obtaining optically pure amino acids by catalyzing the enantioselective opening of stereochemically labile racemic precursors, such as azalactones (Limanto et al, 2005;Truppo and Hughes, 2011;Truppo et al, 2008) and oxazolones (Bevinakatti et al, 1990;Brown et al, 2000;Crich et al, 1993;Gu et al, 1992). Truppo and Hughes recently described a method to prepare the enantiopure ester of (S)-γ-fluoroleucine, an intermediate in the synthesis of the drug odanacatibe, from continuous enzymatic alcoholysis of its respective azalactone using CAL-B immobilized in polymethacrylate resin (Truppo and Hughes, 2011).…”

Section: Dynamic Kinetic Resolution Of Amino Acids and Derivativesmentioning

confidence: 99%

Lipases: Valuable catalysts for dynamic kinetic resolutions

Miranda

Souza

2015

Biotechnology Advances

187

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Section: Dynamic Kinetic Resolution Of Amino Acids and Derivativesmentioning

confidence: 99%

Lipases: Valuable catalysts for dynamic kinetic resolutions

Miranda

Souza

2015

Biotechnology Advances

187

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“…The high cost of the bis-lactim ether precursor and the low-yielding diastereoselective alkylation step prompted Limanto and co-workers to develop a more practical and efficient route for the preparation of this amino acid. [23] After the failure of synthetic attempts based on asymmetric alkylation of N-diphenylmethyleneglycine ethyl ester (17, Scheme 3) with the fluorine-containing electrophiles 18, Limanto et al developed an efficient chemoenzymatic approach to (S)-γ-fluoroleucine ethyl ester. Their strategy once more started from diphenylmethyleneglycine ethyl ester (17) Okuda's group recently reported the synthesis of (3R)-3-fluoro-l-Phe (31, Scheme 4) from (1R,2R)-2-amino-1-phenylpropane-1,3-diol (26) as starting material.…”

Section: Monofluorinated α-Amino Acidsmentioning

confidence: 99%

Recent Advances in the Synthesis of Fluorinated Amino Acids

2011

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Introduction of fluorine atoms or fluorine‐containing groups into amino acids has attracted much attention from bioorganic and medicinal chemists because the resulting fluorinated amino acids have found wide application as potential enzyme inhibitors and antitumor (antibacterial) agents. Additionally, it is well known that replacement of naturally occurring amino acid(s) in some peptide chains with their fluorinated counterparts can significantly increase specific protein–ligand or protein–protein interactions, leading to increases in the proteolytic and thermal stabilities of peptide compounds and, as a result, promote their therapeutic properties. This microreview summarizes important advances in the synthesis of fluorinated amino acids since 2005. The contents are simply divided into three groups on the basis of amino acid types: fluorinated α‐amino acids (F‐αAAs), fluorinated β‐amino acids (F‐βAAs), and fluorinated cyclic amino acids (F‐CAAs).

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“…129 The desired racemic azalactone, efficiently produced in a high-yielding, two-pot, four-step process underwent Novozym 435-catalysed ethanolysis in EtOH/TBME in the presence of 20 mol % of triethylamine to furnish ethyl N-Bz-(S)-g-fluoroleucinate in 80 % isolated yield and 95 % ee (Scheme 1.41). 130 Unfortunately, benzoyl deprotection of the resultant product could not be effected without significant formation of the desfluoro compound. By instead using the 2-(3-butenyl)-oxazolone, the amino acid derivative was produced in comparable yields, but moderate enantioselectivity (78 % ee).…”

Section: Dynamic Kinetic Resolutionmentioning

confidence: 99%