85228-79-1Relevant articles and documents
The preparation of side chain functionalized analogues of coenzyme Q for protein conjugation studies
Daines, Alison M.,Abell, Andrew D.
, p. 2371 - 2375 (2007/10/03)
The synthesis of two analogues of CoQ (10 and 13) suitable for conjugation to a peptide or protein, and hence the development of an ELISA immunoassay, is presented. These analogues were synthesized from the protected quinone, 1-bromo-2-methyl-3,4,5,6-tetramethoxybenzene (1), itself prepared from commercially available CoQ-0 (3). Model coupling studies of one of the analogues (10) to N-acetyl-L-lysine methyl ester and a lysine containing dipeptide (N-acetylglycine-L-lysine methyl ester) were also undertaken as a first step to monoclonial antibody production.
Highly S(N)2'-, (E)-, and antiselective alkylation of allylic phosphates. Facile synthesis of coenzyme Q10
Yanagisawa,Nomura,Noritake,Yamamoto
, p. 1130 - 1136 (2007/10/02)
Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high S(N)2' selectivity. Phosphate leaving groups were highly transstereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-S(N)2' selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.
Quinones. Part 2. General Synthetic Routes to Quinone Derivatives with Modified Polyprenyl Side Chains and the Inhibitory Effects of these Quinones on the Generation of the Slow Reacting Substance of Anaphylaxis (SRS-A)
Terao, Shinji,Shiraishi, Mitsuru,Kato, Kaneyoshi,Ohkawa, Shigenori,Ashida, Yasuko,Maki, Yoshitaka
, p. 2909 - 2920 (2007/10/02)
General synthetic routes to quinone acids (8), quinone amides (9), quinone alcohols (10), and quinone methylketones (11) with polyprenyl side chains, in which allylic alcohols (3) are employed as the key intermediates, are described.The Claisen rearrangements and the Carrol reactions of the allylic alcohols (3) with ethyl orthoacetate and diketen produced the ethyl esters (4) and the methylketones (5), respectively.Quinone products (8), (10), and (11) were recovered by oxidative demethylation of hydroquinone dimethyl ethers (4), (5), and (7) or by acid hydrolysis of hydroquinone bis(methoxymethyl) ethers (4) and (5) followed by ferric chloride oxidation.Amidation of quinone acids (8) led to the formation of quinone amides (9).Inhibitory effects of these quinone derivatives on the generation of the slow reacting substance of anaphylaxis (SRS-A) in the lungs of sensitised guinea pigs are evaluated.
