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Literature DB >> 25071927

Neoglycosylation and neoglycorandomization: Enabling tools for the discovery of novel glycosylated bioactive probes and early stage leads.

Abstract

This review focuses upon the development, scope, and utility of the highly versatile chemoselective alkoxyamine-based 'neoglycosylation' reaction first described by Peri and Dumy. The fundamentals of neoglycosylation and the subsequent development of a 'neoglycorandomization' platform to afford differentially-glycosylated libraries of plant-based natural products, microbial-based natural products, and small molecule-based drugs for drug discovery applications are discussed.

Entities: CellLine Chemical Disease Gene Species

Year: 2014 PMID： 25071927 PMCID： PMC4111257 DOI： 10.1039/C4MD00117F

Source DB: PubMed Journal: Medchemcomm ISSN： 2040-2503 Impact factor: 3.597

57 in total

1. Semisynthetic cyclopamine analogues as potent and orally bioavailable hedgehog pathway antagonists.

Authors: Martin R Tremblay; Marta Nevalainen; Somarajan J Nair; James R Porter; Alfredo C Castro; Mark L Behnke; Lin-Chen Yu; Margit Hagel; Kerry White; Kerrie Faia; Louis Grenier; Matthew J Campbell; Jill Cushing; Caroline N Woodward; Jennifer Hoyt; Michael A Foley; Margaret A Read; Jens R Sydor; Jeffrey K Tong; Vito J Palombella; Karen McGovern; Julian Adams
Journal: J Med Chem Date: 2008-10-09 Impact factor: 7.446

2. Synthesis and biological evaluation of novel lipid A antagonists.

Authors: Francesco Peri; Chiara Marinzi; Marek Barath; Francesca Granucci; Matteo Urbano; Francesco Nicotra
Journal: Bioorg Med Chem Date: 2005-10-03 Impact factor: 3.641

3. Recent advances and future challenges in glycan microarray technology.

Authors: José L de Paz; Peter H Seeberger
Journal: Methods Mol Biol Date: 2012

4. Esperamicins, a novel class of potent antitumor antibiotics. I. Physico-chemical data and partial structure.

Authors: M Konishi; H Ohkuma; K Saitoh; H Kawaguchi; J Golik; G Dubay; G Groenewold; B Krishnan; T W Doyle
Journal: J Antibiot (Tokyo) Date: 1985-11 Impact factor: 2.649

5. Warfarin glycosylation invokes a switch from anticoagulant to anticancer activity.

Authors: Pauline Peltier-Pain; Shannon C Timmons; Agnès Grandemange; Etienne Benoit; Jon S Thorson
Journal: ChemMedChem Date: 2011-06-28 Impact factor: 3.466

6. A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides: Oligosaccharide Chain Length-Dependent Induction of Caspase-9-Mediated Apoptosis.

Authors: Anand Krishnan V Iyer; Maoquan Zhou; Neelam Azad; Hosam Elbaz; Leo Wang; Derek K Rogalsky; Yon Rojanasakul; George A O'Doherty; Joseph M Langenhan
Journal: ACS Med Chem Lett Date: 2010-07-12 Impact factor: 4.345

7. Solution structure of the calicheamicin gamma 1I-DNA complex.

Authors: R A Kumar; N Ikemoto; D J Patel
Journal: J Mol Biol Date: 1997-01-17 Impact factor: 5.469

8. Use of N,O-dimethylhydroxylamine as an anomeric protecting group in carbohydrate synthesis.

Authors: Somnath Dasgupta; Mark Nitz
Journal: J Org Chem Date: 2011-02-18 Impact factor: 4.354

9. Glycosyloxyamine neoglycosylation: a model study using calicheamicin.

Authors: Randal D Goff; Shanteri Singh; Jon S Thorson
Journal: ChemMedChem Date: 2011-02-23 Impact factor: 3.466

10. Enhancing the divergent activities of betulinic acid via neoglycosylation.

Authors: Randal D Goff; Jon S Thorson
Journal: Org Lett Date: 2009-01-15 Impact factor: 6.005

15 in total

Review 1. A comprehensive review of glycosylated bacterial natural products.

Authors: Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal: Chem Soc Rev Date: 2015-11-07 Impact factor: 54.564

2. Synthesis and Application of Methyl N,O-Hydroxylamine Muramyl Peptides.

Authors: Klare M Lazor; Junhui Zhou; Kristen E DeMeester; Elizabeth A D'Ambrosio; Catherine L Grimes
Journal: Chembiochem Date: 2019-03-21 Impact factor: 3.164

3. Influence of Sugar Amine Regiochemistry on Digitoxigenin Neoglycoside Anticancer Activity.

Authors: Jianjun Zhang; Larissa V Ponomareva; Nitin S Nandurkar; Yaxia Yuan; Lei Fang; Chang-Guo Zhan; Jon S Thorson
Journal: ACS Med Chem Lett Date: 2015-08-12 Impact factor: 4.345

4. Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

Authors: Guillaume Pelletier; Aaron Zwicker; C Liana Allen; Alanna Schepartz; Scott J Miller
Journal: J Am Chem Soc Date: 2016-03-01 Impact factor: 15.419

5. Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates.

Authors: Simran Buttar; Julia Caine; Evelyne Goné; Reneé Harris; Jennifer Gillman; Roxanne Atienza; Ritu Gupta; Kimberly M Sogi; Lauren Jain; Nadia C Abascal; Yetta Levine; Lindsay M Repka; Christian M Rojas
Journal: J Org Chem Date: 2018-07-06 Impact factor: 4.354

6. Identification of Neuroprotective Spoxazomicin and Oxachelin Glycosides via Chemoenzymatic Glycosyl-Scanning.

Authors: Jianjun Zhang; Ryan R Hughes; Meredith A Saunders; Sherif I Elshahawi; Larissa V Ponomareva; Yinan Zhang; Sydney R Winchester; Samantha A Scott; Manjula Sunkara; Andrew J Morris; Mark A Prendergast; Khaled A Shaaban; Jon S Thorson
Journal: J Nat Prod Date: 2016-12-28 Impact factor: 4.050