Literature DB >> 24065211

Dual-sugar imaging using isonitrile and azido-based click chemistries.

Yéléna A Wainman1, André A Neves, Shaun Stairs, Henning Stöckmann, Heather Ireland-Zecchini, Kevin M Brindle, Finian J Leeper.   

Abstract

We report the first account of metabolically labelling N-acetylglucosamine, in conjunction with either N-acetylgalactosamine or N-acetylmannosamine using a combination of isonitrile- and azide-based chemistries. With the appropriately labelled fluorescent probe molecules, that react with either the azido or isonitrile groups, the method enabled co-visualisation of cancer cell glycoproteins.

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Year:  2013        PMID： 24065211      PMCID： PMC4246059          DOI： 10.1039/c3ob41805g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  30 in total

1.  Probing mucin-type O-linked glycosylation in living animals.

Authors:  Danielle H Dube; Jennifer A Prescher; Chi N Quang; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2006-03-20       Impact factor: 11.205

2.  Increasing the efficacy of bioorthogonal click reactions for bioconjugation: a comparative study.

Authors:  Christen Besanceney-Webler; Hao Jiang; Tianqing Zheng; Lei Feng; David Soriano del Amo; Wei Wang; Liana M Klivansky; Florence L Marlow; Yi Liu; Peng Wu
Journal:  Angew Chem Int Ed Engl       Date:  2011-07-14       Impact factor: 15.336

3.  Fluorescent live-cell imaging of metabolically incorporated unnatural cyclopropene-mannosamine derivatives.

Authors:  Christian M Cole; Jun Yang; Jolita Šečkutė; Neal K Devaraj
Journal:  Chembiochem       Date:  2013-01-04       Impact factor: 3.164

Review 4.  Glycans in cancer and inflammation--potential for therapeutics and diagnostics.

Authors:  Danielle H Dube; Carolyn R Bertozzi
Journal:  Nat Rev Drug Discov       Date:  2005-06       Impact factor: 84.694

5.  Alkynyl sugar analogs for the labeling and visualization of glycoconjugates in cells.

Authors:  Tsui-Ling Hsu; Sarah R Hanson; Kuniyuki Kishikawa; Sheng-Kai Wang; Masaaki Sawa; Chi-Huey Wong
Journal:  Proc Natl Acad Sci U S A       Date:  2007-02-12       Impact factor: 11.205

Review 6.  Metabolic glycoengineering: sialic acid and beyond.

Authors:  Jian Du; M Adam Meledeo; Zhiyun Wang; Hargun S Khanna; Venkata D P Paruchuri; Kevin J Yarema
Journal:  Glycobiology       Date:  2009-08-12       Impact factor: 4.313

7.  Bifunctional unnatural sialic acids for dual metabolic labeling of cell-surface sialylated glycans.

Authors:  Lianshun Feng; Senlian Hong; Jie Rong; Qiancheng You; Peng Dai; Rongbing Huang; Yanhong Tan; Weiyao Hong; Can Xie; Jing Zhao; Xing Chen
Journal:  J Am Chem Soc       Date:  2013-06-14       Impact factor: 15.419

8.  Development and evaluation of new cyclooctynes for cell surface glycan imaging in cancer cells.

Authors:  Henning Stöckmann; André A Neves; Shaun Stairs; Heather Ireland-Zecchini; Kevin M Brindle; Finian J Leeper
Journal:  Chem Sci       Date:  2011-05       Impact factor: 9.825

9.  Imaging cell surface glycosylation in vivo using "double click" chemistry.

Authors:  André A Neves; Henning Stöckmann; Yelena A Wainman; Joe C-H Kuo; Sarah Fawcett; Finian J Leeper; Kevin M Brindle
Journal:  Bioconjug Chem       Date:  2013-05-16       Impact factor: 4.774

Review 10.  Diversity in cell surface sialic acid presentations: implications for biology and disease.

Authors:  Nissi M Varki; Ajit Varki
Journal:  Lab Invest       Date:  2007-07-16       Impact factor: 5.662
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  9 in total

1.  Exploiting metabolic glycoengineering to advance healthcare.

Authors:  Christian Agatemor; Matthew J Buettner; Ryan Ariss; Keerthana Muthiah; Christopher T Saeui; Kevin J Yarema
Journal:  Nat Rev Chem       Date:  2019-09-06       Impact factor: 34.035

2.  Facile Discovery and Quantification of Isonitrile Natural Products via Tetrazine-Based Click Reactions.

Authors:  Yao-Bing Huang; Wenlong Cai; Antonio Del Rio Flores; Frederick F Twigg; Wenjun Zhang
Journal:  Anal Chem       Date:  2019-12-11       Impact factor: 6.986

3.  Addition of Isocyanide-Containing Amino Acids to the Genetic Code for Protein Labeling and Activation.

Authors:  Yuda Chen; Kuan-Lin Wu; Juan Tang; Axel Loredo; Jordan Clements; Jingqi Pei; Zane Peng; Ruchi Gupta; Xinlei Fang; Han Xiao
Journal:  ACS Chem Biol       Date:  2019-11-14       Impact factor: 5.100

Review 4.  Designing sugar mimetics: non-natural pyranosides as innovative chemical tools.

Authors:  Regis C Saliba; Nicola Lb Pohl
Journal:  Curr Opin Chem Biol       Date:  2016-09-10       Impact factor: 8.822

5.  Stable, Reactive, and Orthogonal Tetrazines: Dispersion Forces Promote the Cycloaddition with Isonitriles.

Authors:  Julian Tu; Dennis Svatunek; Saba Parvez; Albert C Liu; Brian J Levandowski; Hannah J Eckvahl; Randall T Peterson; Kendall N Houk; Raphael M Franzini
Journal:  Angew Chem Int Ed Engl       Date:  2019-06-06       Impact factor: 16.823

6.  Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels-Alder reactions.

Authors:  Anne-Katrin Späte; Verena F Schart; Julia Häfner; Andrea Niederwieser; Thomas U Mayer; Valentin Wittmann
Journal:  Beilstein J Org Chem       Date:  2014-09-22       Impact factor: 2.883

Review 7.  Bio-orthogonal Fluorescent Labelling of Biopolymers through Inverse-Electron-Demand Diels-Alder Reactions.

Authors:  Eszter Kozma; Orsolya Demeter; Péter Kele
Journal:  Chembiochem       Date:  2017-02-01       Impact factor: 3.164

8.  In vivo selective imaging of metabolic glycosylation with a tetrazine-modified upconversion nanoprobe.

Authors:  Ruijing Zhang; Judun Zheng; Tao Zhang
Journal:  RSC Adv       Date:  2020-04-21       Impact factor: 3.361

Review 9.  Bioorthogonal Ligations and Cleavages in Chemical Biology.

Authors:  Youshan Li; Hua Fu
Journal:  ChemistryOpen       Date:  2020-08-14       Impact factor: 2.911
  9 in total

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