- P450Jα: A New, Robust and α-Selective Fatty Acid Hydroxylase Displaying Unexpected 1-Alkene Formation
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Oxyfunctionalization of fatty acids (FAs) is a key step in the design of novel synthetic pathways for biobased/biodegradable polymers, surfactants and fuels. Here, we show the isolation and characterization of a robust FA α-hydroxylase (P450Jα) which catalyses the selective conversion of a broad range of FAs (C6:0-C16:0) and oleic acid (C18:1) with H2O2 as oxidant. Under optimized reaction conditions P450Jα yields α-hydroxy acids all with >95 % regioselectivity, high specific activity (up to 15.2 U mg?1) and efficient coupling of oxidant to product (up to 85 %). Lauric acid (C12:0) turned out to be an excellent substrate with respect to productivity (TON=394 min?1). On preparative scale, conversion of C12:0 reached 83 % (0.9 g L?1) when supplementing H2O2 in fed-batch mode. Under similar conditions P450Jα allowed further the first biocatalytic α-hydroxylation of oleic acid (88 % conversion on 100 mL scale) at high selectivity and in good yields (1.1 g L?1; 79 % isolated yield). Unexpectedly, P450Jα displayed also 1-alkene formation from shorter chain FAs (≤C10:0) showing that oxidative decarboxylation is more widely distributed across this enzyme family than reported previously.
- Armbruster, Julia,Steinmassl, Mathilde,Müller Bogotá, Christina A.,Berg, Gabriele,Nidetzky, Bernd,Dennig, Alexander
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p. 15910 - 15921
(2020/10/29)
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- Synthesis of intermediates in the preparation of ACAT inhibitors
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This invention relates to novel processes for synthesizing intermediates in the preparation of N-aryl and N-heteroarylamide inhibitors of the enzyme acyl coenzyme A: cholesterol acyltransferase (ACAT), and to novel intermediates used in such processes.
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- An Efficient Synthesis of (S)-2-Hexylthiodecanoic Acid
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A short synthesis of (S)-2-hexylthiodecanoic acid from racemic 2-hydroxydecanoic acid is described.This material is useful as a sidechain for ACAT inhibitors.
- Kelly, Sarah E.,LaCour, Thomas G.
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p. 715 - 718
(2007/10/02)
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- Asymmetric α-Acetoxylation of Carboxylic Esters
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Using the readily accessible chiral auxiliaries 1-3 the sulfonamide-shielded O-silylated esters 5 underwent ?-face-selective α-acetoxylation on successive treatment with Pb(OAc)4 and NEt3*HF to give after recrystallization α-acetoxy ester 6 in 55-66percen
- Oppolzer, Wolfgang,Dudfield, Philip
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p. 216 - 219
(2007/10/02)
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- Synthesis of Both the Enantiomers of 4-Dodecanolide, a Defensive Secretion of Rove Beetles
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The enantiomers of 4-dodecanolide, a defensive secretion of rove beetles, were synthesized from (S)- and (R)-2-aminodecanoic acid obtained by the enzymic resolution of the corresponding chloroacetyl derivative.
- Sugai, Takeshi,Mori, Kenji
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p. 2497 - 2500
(2007/10/02)
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