95763-61-4Relevant articles and documents
Methyl-Shifted Farnesyldiphosphate Derivatives Are Substrates for Sesquiterpene Cyclases
Harms, Vanessa,Schr?der, Benjamin,Oberhauser, Clara,Tran, Cong Duc,Winkler, Sven,Dr?ger, Gerald,Kirschning, Andreas
supporting information, p. 4360 - 4365 (2020/06/08)
New sesquiterpene backbones are accessible after biotransformation of presilphiperfolan-8β-ol synthase (BcBOT2), a fungal sesquiterpene synthase, with non-natural farnesyldiphosphates in which methyl groups are shifted by one position toward the diphosphate terminus. One of the macrocycles formed, a new germacrene A derivative, undergoes a Cope rearrangement to iso-β-elemene. Three of the new terpenoids show olfactoric properties that range from an intense peppery note to a citrus, ozone-like, and fruity scent.
Gold nanoparticles decorated with mannose-6-phosphate analogues
Combemale, Stephanie,Assam-Evoung, Jean-Norbert,Houaidji, Sabrina,Bibi, Rashda,Barragan-Montero, Veronique
, p. 1120 - 1149 (2014/02/14)
Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) introduction of spacers on the mannose-6-phosphate analogues via Huisgen's cycloaddition, the Julia reaction, or the thiol-ene reaction under ultrasound activation. With the resulting compounds in hand, gold nanoparticles could be functionalized with various carbohydrate derivatives (glycoconjugates) and then tested for angiogenic activity. It was observed that the length and flexibility of the spacer separating the sugar analogue from the nanoparticle have little influence on the biological response. One particular nanoparticle system substantially inhibits blood vessel growth in contrast to activation by the corresponding monomeric glycoconjugate, thereby demonstrating the importance of multivalency in angiogenic activity.
Synthesis and antimicrobial evaluation of farnesyl diphosphate mimetics
Fairlamb, Ian J.S.,Dickinson, Julia M.,O'Connor, Rachael,Cohen, Louis H.,Van Thiel, Christa F.
, p. 80 - 97 (2007/10/03)
The synthesis and first antimicrobial evaluation of farnesyl diphosphate mimetics are described. Several analogues (10, 12, 13, and 20) are inhibitors of Candida albicans, Shizosaccharomyces pombe, and Saccharomyces cerevisiae. The activities of analogues 10, 12, and 13, which contain a ω-phenyl moiety and a diphosphate isostere, are not attributable to inhibition of sterol biosynthesis via squalene synthase. Two geranyl phenylsulphones (14 and 15) are potent inhibitors of Escherichia coli. Analogue 15 exhibits potent activity towards Salmonella typhimurium and Pseudomonas aeruginosa (MIC - 2μg/mL) and represents the first type of semi-synthetic terpenoid allylic sulphone active against these bacteria.
Selenium dioxide E-methyl oxidation of suitably protected geranyl derivatives - Synthesis of farnesyl mimics
Fairlamb, Ian J.S.,Dickinson, Julia M.,Pegg, Mathew
, p. 2205 - 2208 (2007/10/03)
Difunctional allylic terpenes are important synthetic building blocks. Functionalisation of protected geranyl derivatives by SeO2 provides a convenient route to such compounds. The effect of the geranyl protecting group on the oxidation of the
An Efficient Total Synthesis of (+/-)-Sinulariol-B
Yue, Xiangjun,Lan, Jiong,Li, Jing,Liu, Zuosheng,Lin, Yulin
, p. 133 - 140 (2007/10/03)
The first total synthesis of (+/-)-Sinulariol-B, a marine cembrandiol, was achieved in ten steps and ca. 10 percent overall yield from E-geraniol (8). The key steps were the coupling of sulfone 7 with allylic chloride 6 and the macrocyclization of precursor 5 by sulfone- and thioether-stabilized carbanionic alkylations, respectively.
The first total synthesis of (-)-sinulariol-B and three other cembranoids
Lan, Jiong,Li, Jing,Liu, Zuosheng,Li, Yulin,Chan, Albert S. C.
, p. 1877 - 1885 (2007/10/03)
The first total synthesis of (-)-sinulariol-B, a marine cembrandiol, was achieved from geraniol. Three other cembranoids were also synthesized from (- )-sinulariol-B.
Studies on macrocyclic diterpenoids (XIX) - Total synthesis of (RR/SS)-sinulariol-B
Yue,Li
, p. 671 - 674 (2007/10/02)
The first total synthesis of (RR/SS)-sinulariol-B (1) was achieved in ten steps and ~ 10% overall yield from E-geraniol (8). The key step was the macrocyclization of precursor 5 by thioether-stabilized carbanionic alkylations.
