17173-14-7Relevant articles and documents
Selective ?-1 oxidation of fatty acids by CYP147G1 from Mycobacterium marinum
Child, Stella A.,Rossi, Vanessa P.,Bell, Stephen G.
, p. 408 - 417 (2019)
Background: Cyp147G1 is one of 47 cytochrome P450 encoding genes in Mycobacterium marinum M, a pathogenic bacterium with a high degree of sequence similarity to Mycobacterium tuberculosis and Mycobacterium ulcerans. Cyp147G1 is one of only two of these cyp genes which are closely associated with a complete electron transfer system. Methods: The substrate range of the enzyme was tested in vitro and the activity of CYP147G1 was reconstituted in vivo by co-producing the P450 with the ferredoxin and ferredoxin reductase. Results: Substrates of CYP147G1 include fatty acids ranging from octanoic to hexadecanoic acid. CYP147G1 catalysed the selective hydroxylation of linear and ω-2 methyl branched fatty acids at the ω-1 position (≥ 98%). Oxidation of ω-1 methyl branched fatty acids generated the ω and ω-1 hydroxylation products in almost equal proportions, indicating altered position of hydrogen abstraction. Conclusions: This selectivity of fatty acid hydroxylation inferred that linear species must bind in the active site of the enzyme with the terminal methyl group sequestered so that abstraction at the C–H bonds of the ω-1 position is favoured. With branched substrates, one of the methyl groups must be close to the compound I oxygen atom and enable hydroxylation at the terminal methyl group to compete with the reaction at the ω-1C–H bond. General significance: Hydroxy fatty acids are widely used for industrial, food and medical purposes. CYP147G1 demonstrates high regioselectivity for hydroxylation at a sub-terminal position on a broad range of linear fatty acids, not seen in other CYP enzymes.
Stereospecific synthesis of 23-hydroxyundecylprodiginines and analogues and conversion to antimalarial premarineosins via a Rieske oxygenase catalyzed bicyclization
Kancharla, Papireddy,Lu, Wanli,Salem, Shaimaa M.,Kelly, Jane Xu,Reynolds, Kevin A.
, p. 11674 - 11689 (2014)
Facile and highly efficient synthetic routes for the synthesis of (S)- and (R)-23-hydroxyundecylprodiginines ((23S)-2, and (23R)-2), 23-ketoundecylprodiginine (3), and deuterium-labeled 23-hydroxyundecylprodiginine ([23-d]-2) have been developed. We demon
Regio- and Enantio-selective Chemo-enzymatic C?H-Lactonization of Decanoic Acid to (S)-δ-Decalactone
Manning, Jack,Tavanti, Michele,Porter, Joanne L.,Kress, Nico,De Visser, Sam P.,Turner, Nicholas J.,Flitsch, Sabine L.
, p. 5668 - 5671 (2019/03/29)
The conversion of saturated fatty acids to high value chiral hydroxy-acids and lactones poses a number of synthetic challenges: the activation of unreactive C?H bonds and the need for regio- and stereoselectivity. Here the first example of a wild-type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio- and regioselective C5 hydroxylation of decanoic acid 1 to (S)-5-hydroxydecanoic acid 2 is reported. Subsequent lactonization yields (S)-δ-decalactone 3, a high value fragrance compound, with greater than 90 % ee. Docking studies provide a rationale for the high regio- and enantioselectivity of the reaction.
Characterization of CYP154F1 from Thermobifida fusca YX and Extension of Its Substrate Spectrum by Site-Directed Mutagenesis
Rühlmann, Ansgar,Groth, Georg,Urlacher, Vlada B.
, p. 478 - 485 (2018/02/06)
Previous studies on cytochrome P450 monooxygenases (CYP) from family 154 reported their substrate promiscuity and high activity. Hence, herein, the uncharacterized family member CYP154F1 is described. Screening of more than 100 organic compounds revealed
Chain terminators, the use thereof for nucleic acid sequencing and synthesis and a method of their preparation
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, (2008/06/13)
The invention relates to compounds of general structure (I) or salts thereof, wherein B is a nucleobase, X and Z independently are oxygen or sulphur, Y is hydrogen or hydroxy, which optionally may be protected, R1 is hydrocarbyl, which optionally is substituted with a functional group, R2 is hydrogen or hydrocarbyl, which optionally is substituted with a functional group, A is an electron withdrawing or electron donating group capable of moderating the acetal stability of compound (I), L1 and L2 are hydrocarbon linkers, which may be the same or different, L2, when present, being either (i) connected to L1 via the group A, or (ii) directly connected to L1, the group A then being connected to one of linkers L1 and L2, F is a dye label, Q is a coupling group for F, and l, m and n independently are 0 or 1, with the proviso that l is 1 when m is 1, and l is 1 and m is 1 when n is 1. The compounds of formula (I) are useful as deactivatable chain extension terminators. The invention also relates to the use of the compounds (I) in nucleic acid synthesis and nucleic acid sequencing as well as to a method of preparing compounds of Formula (I).
Strategies of Synthesis based on Cyclohexadienes: Part 3. A Novel Route to Macrolide Aromatic Polyketides
Birch, Arthur J.,Mani, Neelakandha S.,Rao, G. S. R. Subba
, p. 1423 - 1427 (2007/10/02)
A novel route to macrolide aromatic polyketides, having an alkyl-β-resorcylate skeleton has been developed.A formal synthesis of (+/-)-curvularin (1), and (+/-)-lasiodiplodin (3) involving the preparation of the seco acid (31) and the acyclic precursor (34) using a one pot Alder-Rickert reaction from 1,3-dimethoxycyclohexa-1,3-diene (7) and the long-chain acetylenic dienophiles (10) and (11) is reported.
A Chemoenzymatic Route to (-)-Pyrenophorin
Ngooi, T.K.,Scilimati, A.,Guo, Zhi-wei,Sih, Charles J.
, p. 911 - 914 (2007/10/02)
The key penultimate intermediate, (+)-7(S)-hydroxy-4,4-(ethylenedioxy)oct-2-enoic acid (6a), for the synthesis of (-)-pyrenophorin has been prepared by using a chemoenzymatic approach.
