Literature DB >> 23292753

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

Christian M Cole1, Jun Yang1, Jolita Šečkutė1, Neal K Devaraj1.   

Abstract

Sugar coated: We recently developed methylcyclopropenes as low-molecular-weight tetrazine coupling partners. Here, we demonstrate that methylcyclopropenes can meet the stringent steric demands required for metabolic imaging of unnatural mannosamines on live cells. Using sequential azide-alkyne chemistry, we also demonstrate multicolor imaging of two different metabolically incorporated unnatural sugars.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2013        PMID： 23292753      PMCID： PMC4010072          DOI： 10.1002/cbic.201200719

Source DB:  PubMed          Journal:  Chembiochem        ISSN： 1439-4227            Impact factor:   3.164


  32 in total

1.  Metabolic labeling of glycoproteins with chemical tags through unnatural sialic acid biosynthesis.

Authors:  C L Jacobs; K J Yarema; L K Mahal; D A Nauman; N W Charters; C R Bertozzi
Journal:  Methods Enzymol       Date:  2000       Impact factor: 1.600

2.  Expanding the diversity of unnatural cell-surface sialic acids.

Authors:  Sarah J Luchansky; Scarlett Goon; Carolyn R Bertozzi
Journal:  Chembiochem       Date:  2004-03-05       Impact factor: 3.164

3.  Substrate specificity of the sialic acid biosynthetic pathway.

Authors:  C L Jacobs; S Goon; K J Yarema; S Hinderlich; H C Hang; D H Chai; C R Bertozzi
Journal:  Biochemistry       Date:  2001-10-30       Impact factor: 3.162

4.  Versatile biosynthetic engineering of sialic acid in living cells using synthetic sialic acid analogues.

Authors:  Cornelia Oetke; Reinhard Brossmer; Lars R Mantey; Stephan Hinderlich; Rainer Isecke; Werner Reutter; Oliver T Keppler; Michael Pawlita
Journal:  J Biol Chem       Date:  2001-12-20       Impact factor: 5.157

5.  Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation.

Authors:  Eliana Saxon; Sarah J Luchansky; Howard C Hang; Chong Yu; Sandy C Lee; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2002-12-18       Impact factor: 15.419

6.  Homomultimeric complexes of CD22 in B cells revealed by protein-glycan cross-linking.

Authors:  Shoufa Han; Brian E Collins; Per Bengtson; James C Paulson
Journal:  Nat Chem Biol       Date:  2005-06-12       Impact factor: 15.040

Review 7.  Biochemical engineering of the N-acyl side chain of sialic acid: biological implications.

Authors:  O T Keppler; R Horstkorte; M Pawlita; C Schmidt; W Reutter
Journal:  Glycobiology       Date:  2001-02       Impact factor: 4.313

8.  A metabolic labeling approach toward proteomic analysis of mucin-type O-linked glycosylation.

Authors:  Howard C Hang; Chong Yu; Darryl L Kato; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2003-12-01       Impact factor: 11.205

9.  Copper-free click chemistry for dynamic in vivo imaging.

Authors:  Jeremy M Baskin; Jennifer A Prescher; Scott T Laughlin; Nicholas J Agard; Pamela V Chang; Isaac A Miller; Anderson Lo; Julian A Codelli; Carolyn R Bertozzi
Journal:  Proc Natl Acad Sci U S A       Date:  2007-10-17       Impact factor: 11.205

10.  Biosynthesis of a nonphysiological sialic acid in different rat organs, using N-propanoyl-D-hexosamines as precursors.

Authors:  H Kayser; R Zeitler; C Kannicht; D Grunow; R Nuck; W Reutter
Journal:  J Biol Chem       Date:  1992-08-25       Impact factor: 5.157
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  34 in total

Review 1.  Expanding room for tetrazine ligations in the in vivo chemistry toolbox.

Authors:  Jolita Sečkutė; Neal K Devaraj
Journal:  Curr Opin Chem Biol       Date:  2013-09-07       Impact factor: 8.822

2.  In situ synthesis of alkenyl tetrazines for highly fluorogenic bioorthogonal live-cell imaging probes.

Authors:  Haoxing Wu; Jun Yang; Jolita Šečkutė; Neal K Devaraj
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-24       Impact factor: 15.336

3.  Fine-Tuning Strain and Electronic Activation of Strain-Promoted 1,3-Dipolar Cycloadditions with Endocyclic Sulfamates in SNO-OCTs.

Authors:  Eileen G Burke; Brian Gold; Trish T Hoang; Ronald T Raines; Jennifer M Schomaker
Journal:  J Am Chem Soc       Date:  2017-05-31       Impact factor: 15.419

4.  Synthesis and reactivity comparisons of 1-methyl-3-substituted cyclopropene mini-tags for tetrazine bioorthogonal reactions.

Authors:  Jun Yang; Yong Liang; Jolita Šečkutė; K N Houk; Neal K Devaraj
Journal:  Chemistry       Date:  2014-02-24       Impact factor: 5.236

5.  Fast, irreversible modification of cysteines through strain releasing conjugate additions of cyclopropenyl ketones.

Authors:  Natalee J Smith; Katarina Rohlfing; Lisa A Sawicki; Prathamesh M Kharkar; Samantha J Boyd; April M Kloxin; Joseph M Fox
Journal:  Org Biomol Chem       Date:  2018-03-09       Impact factor: 3.876

6.  Bioorthogonal Cycloadditions: Computational Analysis with the Distortion/Interaction Model and Predictions of Reactivities.

Authors:  Fang Liu; Yong Liang; K N Houk
Journal:  Acc Chem Res       Date:  2017-09-06       Impact factor: 22.384

Review 7.  Click Chemistry in Proteomic Investigations.

Authors:  Christopher G Parker; Matthew R Pratt
Journal:  Cell       Date:  2020-02-13       Impact factor: 41.582

Review 8.  Chemistry-enabled methods for the visualization of cell-surface glycoproteins in Metazoans.

Authors:  Kelly N Chuh; Matthew R Pratt
Journal:  Glycoconj J       Date:  2015-04-28       Impact factor: 2.916

Review 9.  Chemical Methods for Encoding and Decoding of Posttranslational Modifications.

Authors:  Kelly N Chuh; Anna R Batt; Matthew R Pratt
Journal:  Cell Chem Biol       Date:  2016-01-21       Impact factor: 8.116

Review 10.  Glycan Engineering for Cell and Developmental Biology.

Authors:  Matthew E Griffin; Linda C Hsieh-Wilson
Journal:  Cell Chem Biol       Date:  2016-01-21       Impact factor: 8.116
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