188416-16-2Relevant articles and documents
Enantioselective transesterification of (±)-6-benzyloxy-2,5,7,8- tetramethyl-3,4-dihydro-2H-1-benzopyran-2-ylmethanol catalyzed by the Amano PS lipase in the ionic liquid [bmim]PF6
Shafikov,Spivak, A. Yu.,Odinokov
, p. 2129 - 2132 (2010)
(S)-(-)-6-Benzyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2- ylmethanol, a synthon for the design of natural α-tocopherol, was obtained by kinetically selective acetylation of the corresponding racemic alcohol in the presence of the Amano PS lipase from Burkholderia cepacia in the ionic liquid 1-butyl-3-methylimidazolinium hexafluorophosphate ([bmim]PF6).
CHINONE-, HYDROCHINOME- AND NAPHTHOCHINONE-ANALOGUES OF VATIQUIONE FOR TREATMENT OF MITOCHONDRIAL DISORDER DISEASES
-
, (2021/04/10)
The disclosure provides therapeutic compositions (i.e., therapeutic agents) and methods of preventing or treating Friedreich's ataxia in a mammalian subject, reducing risk factors, signs and/or symptoms associated with Friedreich's ataxia (e.g. Complex I deficiency), and/or reducing the likelihood or severity of Friedreich's ataxia. The disclosure further provides novel intermediates for the production of said therapeutic compositions and related reduced versions of said therapeutic compositions, which reduce forms may also be used as therapeutic agents (or prodrugs of the therapeutic agent(s)).
Screening of a virtual mirror-image library of natural products
Noguchi, Taro,Oishi, Shinya,Honda, Kaori,Kondoh, Yasumitsu,Saito, Tamio,Ohno, Hiroaki,Osada, Hiroyuki,Fujii, Nobutaka
, p. 7653 - 7656 (2016/07/06)
We established a facile access to an unexplored mirror-image library of chiral natural product derivatives using d-protein technology. In this process, two chemical syntheses of mirror-image substances including a target protein and hit compound(s) allow the lead discovery from a virtual mirror-image library without the synthesis of numerous mirror-image compounds.
A Simple 13C NMR Method for the Discrimination of Complex Mixtures of Stereoisomers: All Eight Stereoisomers of α-Tocopherol Resolved
Lankhorst, Peter P.,Netscher, Thomas,Duchateau, Alexander L. L.
, p. 850 - 855 (2015/11/03)
A simple one-dimensional 13C NMR method is presented to discriminate between stereoisomers of organic compounds with more than one chiral center. By means of this method it is possible to discriminate between all eight stereoisomers of α-tocopherol. To achieve this the chiral solvating agent (S)-(+)-1-(9-anthryl)-2,2,2-trifluoroethanol and the compound of interest were dissolved in high concentrations in chloroform-d, and the nuclear magnetic resonance (NMR) spectrum was recorded at a low temperature. The individual stereoisomers of α-tocopherol were assigned by spikes of the reference compounds. The method was also applied to six other representative examples.
Synthesis and screening of novel vitamin e derivatives for anticancer functions
Chen, Wenbin,Park, Sook Kyung,Yu, Weiping,Xiong, Ailian,Sanders, Bob G.,Kline, Kimberly
, p. 72 - 83 (2013/02/23)
α-TEA, RRR-α-tocopherol ether linked acetic acid, exhibits potent anticancer actions in vitro and in vivo; whereas, the parent molecule has no anticancer activity. In this study, we incorporated fluorine at the chroman head and/or ether linkage between the chroman head and phytyl tail of α-TEA as well as RRR-α-tocopherol to synthesize 6 vitamin E derivatives, and evaluated the anticancer actions in vitro for ability to induce cell death by apoptosis of human MCF-7 and MDA-MB-231 breast cancer cell lines and mouse mammary cancer cell line 66cl-4GFP. All derivatives, with the exception of compound 12, exhibited anticancer properties. The modified α-TEA ether-type phytyl group exhibited the highest pro-apoptotic activity in comparison with α-TEA as well as other vitamin E derivatives.
New possibilities in a synthesis of (2R,4'R,8'R)-α-tocopherol (natural vitamin E)
Spivak, Anna Yu,Shafikov, Ruslan V.,Odinokov, Victor N.
, p. 67 - 75 (2011/06/21)
New methods for the synthesis of homochiral C14 and C 15-terpenoids desired as building blocks for phytilic side chain of natural α-tocopherol have been developed. A natural phytone resulted from the proposed effective method of chlo
Chemoenzymatic synthesis of both enantiomers of α-tocotrienol
Chenevert, Robert,Courchesne, Gabriel,Pelchat, Nicholas
, p. 5389 - 5396 (2007/10/03)
The stereoselective acylation of the achiral chromanedimethanol derivative 1 by vinyl acetate in the presence of Candida antarctica lipase B gave the (S)-monoester 2 in high enantiomeric purity (ee ≥ 98%). Enzymatic hydrolysis of diesters of compound 1 failed to give (R)-monoester 2 in good yield and high ee. Thus, both enantiomers of α-tocotrienol were synthesized from the (S)-monoester 2.
Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative
Chênevert, Robert,Courchesne, Gabriel
, p. 7971 - 7973 (2007/10/03)
The stereoselective acylation of an achiral chromandimethanol derivative by vinyl acetate in the presence of Candida antarctica lipase in organic media gave the corresponding (S)-monoester in high enantiomeric purity (ee=98%). (S)-α-Tocotrienol was synthe
