Skeletal diversity from carbohydrates: use of mannose for the diversity-oriented synthesis of polyhydroxylated compounds.

The application of d-mannose as a multipurpose building block from the chiral pool enabled the diversity-oriented synthesis of an array of cyclic and bicyclic scaffolds with polyhydroxylated appendages with the aim to expand the skeletal diversity in the panorama of glycopeptidomimetic compounds.

[1]  C. Matassini,et al.  Double Reductive Amination and Selective Strecker Reaction of a D-Lyxaric Aldehyde: Synthesis of Diversely Functionalized 3,4,5-Trihydroxypiperidines , 2012 .

[2]  H. Kunz,et al.  Carbohydrate scaffolds for combinatorial syntheses that allow selective deprotection of all four positions independent of the sequence. , 2004, Angewandte Chemie.

[3]  J. Aubé,et al.  Probing Chemical Space with Alkaloid-Inspired Libraries , 2014, Nature chemistry.

[4]  T. Wrodnigg,et al.  Iminosugars and relatives as antiviral and potential anti-infective agents. , 2003, Current topics in medicinal chemistry.

[5]  Bernd Becker,et al.  Molecular diversity through sugar scaffolds. , 2003, Drug discovery today.

[6]  Chi-Huey Wong,et al.  Enzyme in der organischen Synthese: das Problem der molekularen Erkennung von Kohlenhydraten (Teil 2) , 1995 .

[7]  Alessandro Pedretti,et al.  VEGA: a versatile program to convert, handle and visualize molecular structure on Windows-based PCs. , 2002, Journal of molecular graphics & modelling.

[8]  Tudor I. Oprea,et al.  Chemography: the Art of Navigating in Chemical Space , 2000 .

[9]  K. Yasuda,et al.  New polyhydroxylated pyrrolidine, piperidine, and pyrrolizidine alkaloids from Scilla sibirica. , 2002, Journal of natural products.

[10]  A. Watson,et al.  Polyhydroxylated alkaloids -- natural occurrence and therapeutic applications. , 2001, Phytochemistry.

[11]  Stuart L Schreiber,et al.  A planning strategy for diversity-oriented synthesis. , 2004, Angewandte Chemie.

[12]  N. Asano Naturally occurring iminosugars and related compounds: structure, distribution, and biological activity. , 2003, Current topics in medicinal chemistry.

[13]  P. Arya,et al.  Advances in solution- and solid-phase synthesis toward the generation of natural product-like libraries. , 2009, Chemical reviews.

[14]  Sorel Muresan,et al.  ChemGPS-NP: tuned for navigation in biologically relevant chemical space. , 2006, Journal of natural products.

[15]  Stefan Wetzel,et al.  Charting, navigating, and populating natural product chemical space for drug discovery. , 2012, Journal of medicinal chemistry.

[16]  R. Hsung,et al.  An unusual stereoselectivity in the anomeric substitution with carbamates promoted by HNTf2. , 2007, Organic & biomolecular chemistry.

[17]  L. Yadav,et al.  Diversity oriented synthesis of fused-ring 1,3-oxazines from carbohydrates as biorenewable feedstocks , 2008 .

[18]  D. Cavalieri,et al.  Chemical genetics approach to drug discovery by diversity-oriented synthesis (DOS) of peptidomimetics , 2011 .

[19]  P. Compain,et al.  Design, synthesis and biological evaluation of iminosugar-based glycosyltransferase inhibitors. , 2003, Current topics in medicinal chemistry.

[20]  G. Fleet,et al.  Amino-sugar glycosidase inhibitors: versatile tools for glycobiologists. , 1992, Glycobiology.

[21]  A. Trabocchi,et al.  Synthesis of Glycidol‐ and Sugar‐Derived Bicyclic β‐ and γ/δ‐Amino Acids for Peptidomimetic Design , 2005 .

[22]  Gregory P. Tochtrop,et al.  Molecular library synthesis using complex substrates: expanding the framework of triterpenoids. , 2013, The Journal of organic chemistry.

[23]  T. Okamoto,et al.  Iminosugar-producing Thai medicinal plants. , 2005, Journal of natural products.

[24]  Matthew A Cooper,et al.  Drug-likeness and increased hydrophobicity of commercially available compound libraries for drug screening. , 2012, Current topics in medicinal chemistry.

[25]  A. Trabocchi,et al.  Enantiospecific synthesis of 3-aza-6,8-dioxa-bicyclo[3.2.1]octane carboxylic acids from erythrose , 2003 .

[26]  A. Trabocchi,et al.  Diversity-oriented synthesis of morpholine-containing molecular scaffolds. , 2009, Chemistry.

[27]  M. Sankar,et al.  Diversity‐Oriented Synthesis of Useful Chiral Building Blocks from D‐Mannitol , 2011 .

[28]  S. Schreiber,et al.  Pathway development and pilot library realization in diversity-oriented synthesis: exploring Ferrier and Pauson-Khand reactions on a glycal template. , 2002, Chemistry & biology.

[29]  R. Molyneux,et al.  Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application , 2000 .

[30]  J. Porco,et al.  An approach to skeletal diversity using functional group pairing of multifunctional scaffolds. , 2007, Organic letters.

[31]  S. Schreiber,et al.  Target-oriented and diversity-oriented organic synthesis in drug discovery. , 2000, Science.

[32]  Andrea Trabocchi,et al.  Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology , 2013 .

[33]  Lakshmi B. Akella,et al.  Diversity-Oriented Synthesis Approach to Macrocycles via Oxidative Ring Expansion , 2012, Nature chemical biology.

[34]  N. Asano Glycosidase inhibitors: update and perspectives on practical use. , 2003, Glycobiology.

[35]  S. Ley,et al.  Rotamers or diastereomers? An overlooked NMR solution. , 2012, The Journal of organic chemistry.

[36]  C. Dobson Chemical space and biology , 2004, Nature.

[37]  T. Pathak,et al.  Diversity‐Oriented Synthesis of Enantiopure Furofurans from Carbohydrates: An Expedient Approach with Built‐in Michael Acceptor, Masked Aldehyde and Leaving Group in a Single Sugar Derivative , 2013 .

[38]  P. S. Kumar,et al.  A diversity oriented one-pot synthesis of novel iminosugar C-glycosides. , 2014, Chemical communications.

[39]  A. M. Boldi,et al.  Libraries from natural product-like scaffolds. , 2004, Current opinion in chemical biology.

[40]  Vipin Kumar,et al.  A glycal approach towards an efficient and stereodivergent synthesis of polyhydroxypyrrolidines , 2006 .

[41]  David R Spring,et al.  Diversity-oriented synthesis; a challenge for synthetic chemists. , 2003, Organic & biomolecular chemistry.

[42]  S. Ghosh,et al.  Sugar amino acid based scaffolds--novel peptidomimetics and their potential in combinatorial synthesis. , 2002, Combinatorial chemistry & high throughput screening.

[43]  Derek S. Tan,et al.  Diversity-oriented synthesis: exploring the intersections between chemistry and biology , 2005, Nature chemical biology.

[44]  Thierry Kogej,et al.  ChemGPS-NPWeb: chemical space navigation online , 2009, J. Comput. Aided Mol. Des..

[45]  D. Cavalieri,et al.  A Systems Biology Approach to Dissection of the Effects of Small Bicyclic Peptidomimetics on a Panel of Saccharomyces cerevisiae Mutants* , 2010, The Journal of Biological Chemistry.

[46]  Rohan A Davis,et al.  Guiding principles for natural product drug discovery. , 2012, Future medicinal chemistry.

[47]  R. Hicklin,et al.  A ring-distortion strategy to construct stereochemically complex and structurally diverse compounds from natural products. , 2013, Nature chemistry.

[48]  D. Cavalieri,et al.  Chemical genetics approach to identify new small molecule modulators of cell growth by phenotypic screening of Saccharomyces cerevisiae strains with a library of morpholine-derived compounds. , 2010, Organic & biomolecular chemistry.

[49]  Jürgen Bajorath,et al.  Cell-based partitioning. , 2004, Methods in molecular biology.

[50]  Derek S. Tan,et al.  Expanding the range of 'druggable' targets with natural product-based libraries: an academic perspective. , 2010, Current opinion in chemical biology.

[51]  A. Trabocchi,et al.  Skeletal diversity by sequential one-pot and stepwise routes using morpholine ester scaffolds , 2010 .

[52]  J. MacMillan,et al.  Hunanamycin A, an antibiotic from a marine-derived Bacillus hunanensis. , 2013, Organic letters.

[53]  Wolfgang H. B. Sauer,et al.  Molecular Shape Diversity of Combinatorial Libraries: A Prerequisite for Broad Bioactivity , 2003, J. Chem. Inf. Comput. Sci..

[54]  M. Gil,et al.  Chemistry of Epoxysulfones: A New Route to Polyhydroxylated Pyrrolidines , 2005 .

[55]  Gemma L Thomas,et al.  Natural product-like synthetic libraries. , 2011, Current opinion in chemical biology.

[56]  M. Sofia Carbohydrate-based combinatorial libraries , 1997, Molecular Diversity.