388091-45-0Relevant articles and documents
Dienophile-Modified Mannosamine Derivatives for Metabolic Labeling of Sialic Acids: A Comparative Study
Dold, Jeremias E. G. A.,Pfotzer, Jessica,Sp?te, Anne-Katrin,Wittmann, Valentin
, p. 1242 - 1250 (2017)
Sialic acids play an important role in numerous cell adhesion processes, and sialylation levels are known to be altered under certain pathogenic conditions, such as cancer. Metabolic glycoengineering with mannosamine derivatives is a convenient way to introduce non-natural chemical reporter groups into sialylated glycoconjugates, offering the opportunity to label sialic acids by using bioorthogonal ligation chemistry. The labeling intensity depends not only on the rate of the ligation reaction but also on the extent to which the natural sialic acids are replaced by the modified ones; that is, the incorporation efficiency. Here, we present a comparative study of eight mannosamine derivatives featuring terminal alkenes as chemical reporter groups that can be labeled by an inverse-electron-demand Diels–Alder (DAinv) reaction. The derivatives differed in chain length as well as the type of linkage (carbamates, amides, and a urea) that connects the terminal alkene to the sugar. As a general trend, increasing chain lengths resulted in higher DAinv reactivity and, at the same time, reduced incorporation efficiency. Carbamates were better accepted than amides with the same chain length; nevertheless, the latter resulted in more intense cell-surface staining, visible by live-cell fluorescence microscopy. A urea derivative was also shown to be accepted.
Rapid isolation of novel FK506 binding proteins from multiple organisms using gDNA and cDNA T7 phage display
Piggott, Andrew M.,Kriegel, Alison M.,Willows, Robert D.,Karuso, Peter
, p. 6841 - 6850 (2009)
Reverse chemical proteomics using T7 phage display is a powerful technique for identifying cellular receptors of biologically active small molecules. However, to date this method has generally been limited to cDNA libraries constructed from mRNA isolated from eukaryotes. In this paper, we describe the construction of the first prokaryotic T7 phage display libraries from randomly digested Pseudomonas stutzeri and Vibrio fischeri gDNA, as well as a plant cDNA library from Arabidopsis thaliana. We also describe the use of T7 phage display to identify novel proteins from environmental DNA samples using biotinylated FK506 as a model affinity probe.
Domino metathesis of 3,6-dihydro-1,2-oxazine: Access to isoxazolo[2,3-a]pyridin-7-ones
Calvet, Geraldine,Blanchard, Nicolas,Kouklovsky, Cyrille
, p. 1485 - 1488 (2007)
Equation presented Strained bicyclic 3,6-dihydro-1,2-oxazine is a reactive substrate in domino metathesis with an external alkene. This general transformation leads to isoxazolo[2,3-a]pyridin-7-one, a versatile scaffold combining chemical functions that c
Synthetic approaches to racemic porantheridine and 8-epihalosaline via a nitroso diels-alder cycloaddition/ring-rearrangement metathesis sequence
Sancibrao, Pierre,Karila, Delphine,Kouklovsky, Cyrille,Vincent, Guillaume
, p. 4333 - 4336 (2010)
The application of a sequence involving a nitroso Diels-Alder cycloaddition and a ring-rearrangement metathesis to the total synthesis of (±)-8-epihalosaline and the formal synthesis of (±)-porantheridine is described. The formation of the 2,6-trans-disubstituted piperidine backbone of porantheridine has been accomplished by addition of a Grignard reagent onto an N-benzylpiperidone followed by a highly diastereoselective reduction of the imminium intermediate in one pot.
MACROCYCLIC SPIROCARBAMATE DERIVATIVES AS FACTOR XIA INHIBITORS, PHARMACEUTICALLY ACCEPTABLE COMPOSITIONS AND THEIR USE
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Page/Page column 31, (2017/07/05)
The present invention provides a compound of Formula (I) and stereoisomers thereof, and pharmaceutically acceptable salts of said compounds and said stereoisomers, and pharmaceutical compositions thereof, and methods for using said compounds and compositi
Genetically encoded unstrained olefins for live cell labeling with tetrazine dyes
Lee, Yan-Jiun,Kurra, Yadagiri,Yang, Yanyan,Torres-Kolbus, Jessica,Deiters, Alexander,Liu, Wenshe R.
supporting information, p. 13085 - 13088 (2015/02/19)
A number of non-canonical amino acids (NCAAs) with unstrained olefins are genetically encoded using mutant pyrrolysyl-tRNA synthetase-tRNAPylCUA pairs. These NCAAs readily undergo inverse electron-demand Diels-Alder cycloadditions with tetrazine dyes, leading to selective labeling of proteins bearing these NCAAs in live cells. This journal is
Ring-rearrangement metathesis of nitroso Diels-Alder cycloadducts
Vincent, Guillaume,Kouklovsky, Cyrille
supporting information; experimental part, p. 2972 - 2980 (2011/04/24)
Strained nitroso Diels-Alder bicyclo[2.2.1] or [2.2.2] adducts functionalized with alkene side chains of diverse length undergo a ring-rearrangement metathesis process with external alkenes and Grubbs II or Hoveyda-Grubbs II ruthenium catalysts, under microwave irradiation or classical heating, to deliver cis-fused bicycles of various ring sizes, which contain a N-O bond. These scaffolds are of synthetic relevance for the generation of molecular diversity and to the total synthesis of alkaloids. The observation of unexpected reactions, such as epimerization or one-carbon homologation of the alkene side chain, is also reported.
Four-component reactions toward fused heterocyclic rings
Airiau, Etienne,Girard, Nicolas,Mann, Andre,Salvadori, Jessica,Taddei, Maurizio
supporting information; experimental part, p. 5314 - 5317 (2010/02/28)
A multicomponent reaction between H2, CO, an unsaturated carboxylic acid derivative, and binucleophiles has been discovered. This process represents a combination of diversity-oriented synthesis and multicomponent reactions including amidation and hydroformylation, followed by nucleophilic addition to an N-acyliminium ion allowing the generation of six new bonds. Using π-nucleophiles, the sequence turns into a multicomponent Pictet-Spengler reaction.
