75853-49-5Relevant articles and documents
Biotechnological Production of Methyl-Branched Aldehydes
Fraatz, Marco Alexander,Goldmann, Michael,Geissler, Torsten,Gross, Egon,Backes, Michael,Hilmer, Jens-Michael,Ley, Jakob,Rost, Johanna,Francke, Alexander,Zorn, Holger
, p. 2387 - 2392 (2018)
A number of methyl-branched aldehydes impart interesting flavor impressions, and especially 12-methyltridecanal is a highly sought after flavoring compound for savory foods. Its smell is reminiscent of cooked meat and tallow. For the biotechnological production of 12-methyltridecanal, the literature was screened for fungi forming iso-fatty acids. Suitable organisms were identified and successfully grown in submerged cultures. The culture medium was optimized to increase the yields of branched fatty acids. A recombinant carboxylic acid reductase was used to reduce 12-methyltridecanoic acid to 12-methyltridecanal. The efficiency of whole-cell catalysis was compared to that of the purified enzyme preparation. After lipase-catalyzed hydrolysis of the fungal lipid extracts, the released fatty acids were converted to the corresponding aldehydes, including 12-methyltridecanal and 12-methyltetradecanal.
Biotechnological Production of Odor-Active Methyl-Branched Aldehydes by a Novel α-Dioxygenase from Crocosphaera subtropica
Albrecht, Florian,Buchhaupt, Markus,Fraatz, Marco A.,Geissler, Torsten,Hahne, Friederike,Hammer, Andreas K.,Jordan, Paulina,Ley, Jakob,Schrader, Jens,Zorn, Holger
, p. 10432 - 10440 (2020/10/26)
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 α-dioxygenase from Crocosphaera subtropica was heterologously expressed in Escherichia coli and applied for the biotechnological production of C12-C15 branched-chain fatty aldehydes. The enzyme has a sequence identity of less than 40% to well-investigated α-dioxygenase from rice. Contrary to the latter, it efficiently transformed short-chained fatty acids. The kinetic parameters of α-dioxygenase toward unbranched and iso-branched-chain substrates were studied by means of an oxygen-depletion assay. The transformation products (C12-C15 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 C14 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.
Synthesis of ent-BE-43547A 1 reveals a potent hypoxia-selective anticancer agent and uncovers the biosynthetic origin of the APD-CLD natural products
Villadsen, Nikolaj L.,Jacobsen, Kristian M.,Keiding, Ulrik B.,Weibel, Esben T.,Christiansen, Bj?rn,Vosegaard, Thomas,Bjerring, Morten,Jensen, Frank,Johannsen, Mogens,T?rring, Thomas,Poulsen, Thomas B.
, p. 264 - 272 (2017/03/09)
Tumour hypoxia is speculated to be a key driver of therapeutic resistance and metastatic dissemination. Consequently, the discovery of new potent agents that selectively target the hypoxic cell population may reveal new and untapped antitumour mechanisms. Here we demonstrate that the BE-43547 subclass of the APD-CLD (amidopentadienoate-containing cyclolipodepsipeptides) natural products possesses highly hypoxia-selective growth-inhibitory activity against pancreatic cancer cells. To enable this discovery, we have developed the first synthesis of the BE-43547-macrocyclic scaffold in 16 steps (longest linear sequence), which also allowed access to the full panel of relative stereoisomers and ultimately to the assignment of stereochemical configuration. Discrepancies between the spectroscopic signatures of the synthetic compounds with that originally reported for the BE-43547 members stimulated us to re-isolate the natural product from a BE-43547-producing microorganism during which we elucidated the biosynthetic gene clusters for the BE-43547 family as well as for all other known APD-CLDs. Our studies underline the exciting possibilities for the further development of the anticancer activities of these natural products.
