474404-92-7Relevant academic research and scientific papers
Unified total syntheses of the inositol polyphosphates: D-I-3,5,6P 3, D-I-3,4,5P3, D-I-3,4,6P3, and D-I-3,4,5,6P4 via catalytic enantioselective and site-selective phosphorylation
Morgan, Adam J.,Komiya, Shio,Xu, Yingju,Miller, Scott J.
, p. 6923 - 6931 (2006)
Synthetic routes to various inositol polyphosphates have been discovered utilizing catalytic enantioselective and site-selective phosphorylation reactions. The syntheses described herein exploit a common intermediate to gain efficient access to eight unique inositol polyphosphates.
Outer-Sphere Control for Divergent Multicatalysis with Common Catalytic Moieties
Shugrue, Christopher R.,Sculimbrene, Bianca R.,Jarvo, Elizabeth R.,Mercado, Brandon Q.,Miller, Scott J.
supporting information, p. 1664 - 1672 (2019/01/26)
We herein report two examples of one-pot, simultaneous reactions, mediated by multiple, orthogonal catalysts with the same catalytic motif. First, BINOL-derived chiral phosphoric acids (CPA) and phosphothreonine (pThr)-embedded peptides were found to be matched for two different steps in double reductions of bisquinolines. Next, two -methylhistidine (Pmh)-containing peptides catalyzed enantio- and chemoselective acylations and phosphorylations of multiple substrates in one pot. The selectivity exhibited by common reactive moieties is adjusted solely by the appended chiral scaffold through outer-sphere interactions.
Insights into the structural specificity of the cytotoxicity of 3-deoxyphosphatidylinositols
Wang, Yanling K.,Chen, Wei,Blair, Derek,Pu, Mingming,Xu, Yingju,Miller, Scott J.,Redfield, Alfred G.,Chiles, Thomas C.,Roberts, Mary F.
, p. 7746 - 7755 (2008/12/22)
D-3-Deoxyphosphatidylinositol (D-3-deoxy-PI) derivatives have cytotoxic activity against various human cancer cell lines. These phosphatidylinositols have a potentially wide array of targets in the phosphatidylinositol-3-kinase (PI3K)/Akt signaling networ
Catalyst-dependent syntheses of phosphatidylinositol-5-phosphate-DiC8 and its enantiomer
Kayser-Bricker, Katherine J.,Jordan, Peter A.,Miller, Scott J.
, p. 7015 - 7020 (2008/09/21)
Peptide-based catalysts have been applied to the enantioselective syntheses of the title compounds, with this being the first report of the synthesis of an ent-PI5P analogue. The key steps in the synthesis involve asymmetric phosphorylation catalysis. Add
Enantiodivergence in small-molecule catalysis of asymmetric phosphorylation: Concise total syntheses of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate
Sculimbrene, Bianca R.,Morgan, Adam J.,Miller, Scott J.
, p. 11653 - 11656 (2007/10/03)
Peptide-based catalysts have been found that catalyze the enantiodivergent phosphorylation of a meso myo-inositol-derived triol (1). The sequential screening of random peptide libraries, followed by the evaluation of a focused library, led to the identifi
