Biotechnological Production of Odor-Active Methyl-Branched Aldehydes by a Novel α-Dioxygenase from Crocosphaera subtropica

被引:19
作者
Hammer, Andreas K. [1 ]
Albrecht, Florian [1 ]
Hahne, Friederike [1 ]
Jordan, Paulina [2 ]
Fraatz, Marco A. [1 ,3 ]
Ley, Jakob [4 ]
Geissler, Torsten [4 ]
Schrader, Jens [2 ]
Zorn, Holger [1 ,3 ]
Buchhaupt, Markus [2 ]
机构
[1] Justus Liebig Univ Giessen, Inst Food Chem & Food Biotechnol, Heinrich Buff Ring 17, D-35392 Giessen, Germany
[2] DECHEMA Res Inst, Ind Biotechnol, D-60486 Frankfurt, Germany
[3] Fraunhofer Inst Mol Biol & Appl Ecol, D-35394 Giessen, Germany
[4] Symrise AG, D-37603 Holzminden, Germany
关键词
methyl-branched aldehydes; flavoring substances; alpha-dioxygenase; Crocosphaera subtropica (former Cyanothece sp. ATCC 51142); odor threshold; FATTY-ACIDS; HIGHER-PLANTS; OXIDATION; IDENTIFICATION; OXYGENASE; ENZYME; BIOSYNTHESIS; PEROXIDASE; ANALOGS; GREEN;
D O I
10.1021/acs.jafc.0c02035
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
As a result of their pleasant odor qualities and low odor thresholds, iso- and anteiso-fatty aldehydes represent promising candidates for applications in flavoring preparations. A novel cyanobacterial alpha-dioxygenase from Crocosphaera subtropica was heterologously expressed in Escherichia coli and applied for the biotechnological production of C-12-C-15 branched-chain fatty aldehydes. The enzyme has a sequence identity of less than 40% to well-investigated alpha-dioxygenase from rice. Contrary to the latter, it efficiently transformed short-chained fatty acids. The kinetic parameters of alpha-dioxygenase toward unbranched and iso-branched-chain substrates were studied by means of an oxygen-depletion assay. The transformation products (C-12-C-15 iso- and anteiso-aldehydes) were extensively characterized, including their sensory properties. The aldehydes exhibited green-soapy, sweety odors with partial citrus-like, metallic, peppery, and savory-tallowy nuances. Moreover, the two C-14 isomers showed particularly low odor threshold values of 0.2 and 0.3 ng/L in air as determined by means of gas chromatography-olfactometry.
引用
收藏
页码:10432 / 10440
页数:9
相关论文
共 51 条
[1]   Enantioselective α-hydroperoxylation of long-chain fatty acids with crude enzyme of marine green alga Ulva pertusa [J].
Akakabe, Y ;
Matsui, K ;
Kajiwara, T .
TETRAHEDRON LETTERS, 1999, 40 (06) :1137-1140
[2]  
[Anonymous], 2013, EFSA Journal
[3]  
[Anonymous], 1993, P 3 INT HAARMANN REI
[4]   Optimization of protein purification and characterization using Thermofluor screens [J].
Boivin, Stephane ;
Kozak, Sandra ;
Meijers, Rob .
PROTEIN EXPRESSION AND PURIFICATION, 2013, 91 (02) :192-206
[5]  
Borge GIA, 1997, BBA-LIPID LIPID MET, V1344, P47
[6]  
Burdock G.A., 2010, Fenaroli's handbook of flavour ingredients, V6th, DOI DOI 10.1201/9781439847503
[7]   Characterization of the Key Aroma Compounds in Beef and Pork Vegetable Gravies a la Chef by Application of the Aroma Extract Dilution Analysis [J].
Christlbauer, Monika ;
Schieberle, Peter .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (19) :9114-9122
[8]   Carboxylic acid reductases (CARs): An industrial perspective [J].
Derrington, Sasha R. ;
Turner, Nicholas J. ;
France, Scott P. .
JOURNAL OF BIOTECHNOLOGY, 2019, 304 :78-88
[9]   Flavouring Group Evaluation 01, Revision 2 (FGE.01Rev2): Branched-chain aliphatic saturated aldehydes, carboxylic acids and related esters of primary alcohols and branched-chain carboxylic acids from chemical groups 1 and 2 [J].
EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids .
EFSA JOURNAL, 2010, 8 (11)
[10]   Biotechnological Production of Methyl-Branched Aldehydes [J].
Fraatz, Marco Alexander ;
Goldmann, Michael ;
Geissler, Torsten ;
Gross, Egon ;
Backes, Michael ;
Hilmer, Jens-Michael ;
Ley, Jakob ;
Rost, Johanna ;
Francke, Alexander ;
Zorn, Holger .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2018, 66 (10) :2387-2392