- Synthesis of a 2-indolylphosphonamide derivative with inhibitory activity against yersiniabactin biosynthesis
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We report the synthesis of an adenosyl-derived indolylphosphonamide analogue of salicyladenosylmonophosphate involved in the plague and tuberculosis siderophore biosyntheses. The compound proved to be a potent inhibitor of the Yersinia pestis salicylate a
- Bisseret, Philippe,Thielges, Sabine,Bourg, Stéphane,Miethke, Marcus,Marahiel, Mohamed A.,Eustache, Jacques
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- CHEMOSELECTIVE THIOL-CONJUGATION WITH ALKENE OR ALKYNE-PHOSPHONOTHIOLATES AND -PHOSPHONATES
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Disclosed are novel conjugates and processes for the preparation thereof. A process for the preparation of alkene-or alkyne-phosohonothiolates and -phosphonates comprises the step of: reacting a compound of formula (I) with a thiol-containing molecule of
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Page/Page column 83; 84
(2019/10/01)
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- Lipidomics characterization of biosynthetic and remodeling pathways of cardiolipins in genetically and nutritionally manipulated yeast cells
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Cardioipins (CLs) are unique tetra-acylated phospholipids of mitochondria and define the bioenergetics and regulatory functions of these organelles. An unresolved paradox is the high uniformity of CL molecular species (tetra-linoleoyl-CL) in the heart, liver, and skeletal muscles-in contrast to their high diversification in the brain. Here, we combined liquid chromatography-mass-spectrometry-based phospholipidomics with genetic and nutritional manipulations to explore CLs' biosynthetic vs postsynthetic remodeling processes in S. cerevisiae yeast cells. By applying the differential phospholipidomics analysis, we evaluated the contribution of Cld1 (CL-specific phospholipase A) and Taz1 (acyl-transferase) as the major regulatory mechanisms of the remodeling process. We further established that nutritional "pressure" by high levels of free fatty acids triggered a massive synthesis of homoacylated molecular species in all classes of phospholipids, resulting in the preponderance of the respective homoacylated CLs. We found that changes in molecular speciation of CLs induced by exogenous C18-fatty acids (C18:1 and C18:2) in wild-type (wt) cells did not occur in any of the remodeling mutant cells, including cld1Δ, taz1Δ, and cld1Δtaz1Δ. Interestingly, molecular speciation of CLs in wt and double mutant cells cld1Δtaz1Δ was markedly different. Given that the bioenergetics functions are preserved in the double mutant, this suggests that the accumulated MLCL-rather than the changed CL speciation-are the likely major contributors to the mitochondrial dysfunction in taz1Δ mutant cells (also characteristic of Barth syndrome). Biochemical studies of Cld1 specificity and computer modeling confirmed the hydrolytic selectivity of the enzyme toward C16-CL substrates and the preservation of C18:1-containing CL species.
- Tyurina, Yulia Y.,Lou, Wenjia,Qu, Feng,Tyurin, Vladimir A.,Mohammadyani, Dariush,Liu, Jenney,Huttemann, Maik,Frasso, Michael A.,Wip, Peter,Bayir, Hulya,Greenberg, MiriaM. L.,Kagan, Valerian E.
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p. 265 - 281
(2018/01/02)
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- Reactions of benzyl methyl substituted-benzyl phosphites with tert- butyl hypochlorite: 'Balanced TS' validating reactivity/selectivity principle
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Reactions of a series of several benzyl methyl substituted-benzyl phosphites with tert-butyl hypochlorite were investigated. The reactions produced phosphates, isobutene, alkyl chlorides, and benzyl chlorides via phosphonium chlorides as intermediates. Fu
- Kim, Sung Soo,Zhu, Yu,Oh, In Seok,Lim, Chang Gyeong
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p. 836 - 842
(2007/10/03)
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- Synthesis and structure of cellular mediators: Inositol polyphosphate diphosphates
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The first total syntheses of 1-O-[(phosphonooxy)hydroxyphosphinyl]-2,3,4,5,6-pentakis-O-phosphono-D myo-inositol (10) and its antipode (11) were achieved from enantiopure 2,3:5,6-di-O-cyclohexylidene-D-myo-inositol (6). The critical pyrophosphate function
- Falck,Reddy, K. Kishta,Ye, Jianhua,Saady, Mourad,Mioskowski, Charles,Shears, Stephen B.,Tan, Zheng,Safrany, Stephen
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p. 12172 - 12175
(2007/10/03)
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- Nucleoside 3'-N,N-dialkylphosphonamidates: Novel building blocks for oligonucleotide synthesis
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Nucleoside 3'-N,N-diisopropylphosphonamidates reacted with tris(2,4,6-tribromophenoxy)dichlorophosphorane (BDCP) to generate the corresponding aminophosphorochloridites without cleavage of the P-N bond. The reaction was applied to internucleotidic bond formation.
- Wada,Ishikawa,Hata
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p. 6363 - 6366
(2007/10/02)
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- AN INVESTIGATION OF SEVERAL DEOXYNUCLEOSIDE PHOSPHORAMIDITES USEFUL FOR SYNTHESIZING DEOXYOLIGONUCLEOTIDES
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Various deoxynucleoside N,N-dialkylaminomethoxyphosphines were examined for stability and reactivity in deoxyoligonucleotide synthesis.Of those examined, the N-morpholino and N,N-diisopropylamino derivatives most completely satisfied all criteria.
- McBride, L. J.,Caruthers, M. H.
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p. 245 - 248
(2007/10/02)
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