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- Title
P450<sub>Jα</sub>: A New, Robust and α‐Selective Fatty Acid Hydroxylase Displaying Unexpected 1‐Alkene Formation.
- Authors
Armbruster, Julia; Steinmassl, Mathilde; Müller Bogotá, Christina A.; Berg, Gabriele; Nidetzky, Bernd; Dennig, Alexander
- Abstract
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.
- Subjects
FATTY acids; LAURIC acid; OLEIC acid; HYDROXY acids; HYDROXYLATION; BIOSURFACTANTS
- Publication
Chemistry - A European Journal, 2020, Vol 26, Issue 68, p15910
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201905511