- Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents
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Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles p
- Kim, Min Ju,Lee, Suk Ho,Park, So Ok,Kang, Hyunku,Lee, Jun Sung,Lee, Ki Nam,Jung, Myung Eun,Kim, Jeongmin,Lee, Jinhwa
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experimental part
p. 5468 - 5479
(2011/10/30)
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- Glycan array on aluminum oxide-coated glass slides through phosphonate chemistry
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A new type of glycan array covalently or noncovalently attached to aluminum oxide-coated glass (ACG) slides has been developed for studies of enzymatic reactions and protein binding. To prepare the noncovalent array, glycans with a polyfluorinated hydrocarbon (-C8F17) tail are spotted robotically onto the ACG slide surface containing a layer of polyfluorinated hydrocarbon terminated with phosphonate. After incubation and washing, the noncovalent array can be characterized by MS-TOF via ionization/desorption at a low laser energy without addition of matrix. A representive cellotetraose array was developed to study the activity and specificity of different cellulases and to differentiate the exo-and endoglucanase activities. To prepare the covalent array, glycans with a phosphonic acid tail were synthesized and spotted robotically onto the ACG slide surface. After incubation, the slides can be used directly for quantitative protein binding analysis. Compared to the preparation of glycan arrays on glass slides and other surfaces, this method of arraying using phosphonic acid reacting with ACG is more direct, convenient, and effective and represents a new platform for the high-throughput analysis of protein-glycan interactions.
- Chang, Shih-Huang,Han, Jeng-Liang,Tseng, Susan Y.,Lee, Hsin-Yu,Lin, Chin-Wei,Lin, Yu-Chen,Jeng, Wen-Yih,Wang, Andrew H.-J.,Wu, Chung-Yi,Wong, Chi-Huey
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supporting information; experimental part
p. 13371 - 13380
(2010/11/18)
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- On the synthesis of pyrinodemin A. Part 1: The location of the olefin
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The elucidation of the structure of the cytotoxic marine sponge alkaloid pyrinodemin A by synthesis is described. Based on the 13C NMR spectra of three double bond positional isomers and the natural product, it is concluded the C14′-C15′ isomer
- Romeril, Stuart P.,Lee, Victor,Baldwin, Jack E.,Claridge, Timothy D.W.
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p. 1127 - 1140
(2007/10/03)
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- Synthesis of a possible structure of pyrinodemin A
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An alternative possible structure of pyrinodemin A is synthesised. The 13C NMR of the synthetic product 3 is in better agreement with the literature data.
- Romeril, Stuart P.,Lee, Victor,Claridge, Timothy D.W.,Baldwin, Jack E.
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p. 327 - 329
(2007/10/03)
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- A short synthesis of 4-substituted 1-(hydroxyalkyl)-1H-pyrazolo[3,4-d]pyrimidines
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A simple and practical procedure was developed for the preparation of 4-substituted-1-(hydroxyalkyl)-1H-pyrazolo[3,4-d]pyrimidines. This was achieved by reacting nucleobase 3a or 3b with cesium carbonate or DBU in the presence of various alkyl iodides at 0°C in DMF. This procedure appears to be of general utility, proceeds in reasonable yield, and is applicable to different alkyl chain lengths including protected and unprotected alcohols. The synthetic utility of this approach is demonstrated by the facile synthesis of ST 689, a potent immunostimulatory drug.
- Zacharie, Boulos,Connolly, Timothy P.,Rej, Rabindra,Attardo, Giorgio,Penney, Christopher L.
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p. 2271 - 2278
(2007/10/03)
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- Structure determination of an endogenous sleep-inducing lipid, cis-9-octadecenamide (oleamide): A synthetic approach to the chemical analysis of trace quantities of a natural product
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The pursuit of endogenous sleep-inducing substances has been the focus of an extensive, complicated body of research. Several compounds, including Δ-sleep-inducing peptide and prostaglandin D2, have been suggested to play a role in sleep induction, and yet, the molecular mechanisms of this physiological process remain largely unknown. In recent efforts, the cerebrospinal fluid of sleep-deprived cats was analyzed in search of compounds that accumulated during sleep deprivation. An agent with the chemical formula C18H35NO was found to cycle with sleep-wake patterns, increasing in concentration with sleep deprivation and decreasing in amount upon recovery sleep. Since the material was generated in minute quantities and only under the special conditions of sleep deprivation, efforts to isolate sufficient material for adequate characterization, structure identification, and subsequent detailed evaluation of its properties proved unrealistic. With the trace amounts of the impure endogenous compound available, extensive MS studies on the agent were completed, revealing key structural features of the molecule including two degrees of unsaturation, a long alkyl chain, and a nitrogen substituent capable of fragmenting as ammonia. Additionally, HPLC traces suggested a weak UV absorbance for the unknown material. With this data in hand and encouraged by the relatively small size of the molecule, MW = 281, a synthetic approach toward the structural identification of the natural compound was initiated. Herein, we report the full details of the synthesis and comparative characterization of candidate structures for this endogenous agent that led to the unambiguous structural correlation with synthetic cis-9-octadecenamide.
- Cravatt, Benjamin F.,Lerner, Richard A.,Boger, Dale L.
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p. 580 - 590
(2007/10/03)
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- Synthesis and conformational analysis of 2,9-disubstituted 1-oxaquinolizidines
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The synthesis of (2S,9R,10S)-9-(5-((tert-butyldiphenylsilyl)oxy)pentyl)-2-(hydroxymethy l)-1-oxaquinolizidine (29a) from (S)-malic acid, 1,5-pentanediol, and trifluoroacetamide is reported. Conformational analysis using molecular mechanics calculations an
- Borjesson,Csoregh,Welch
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p. 2989 - 2999
(2007/10/02)
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- Triply Convergent, Stereospecific Alkene Formation via Peterson Olefination
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α-Iodo silanes 8 were prepared from α-hydroxy silanes and after halogen/metal exchange and treatment with copper(I)bromide-dimethyl sulfide were coupled with acid chlorides to yield α-silyl ketones 2.Cram controlled addition with a variety of nucleophiles followed by treatment with acid or base led to either the (E)- or (Z)-alkene in good overall yields from the iodide (47-67percent) and with excellent stereoselectivities (>95/95/5 isomeric purity.
- Barrett, Anthony G. M.,Flygare, John A.
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p. 638 - 642
(2007/10/02)
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