Literature DB >> 27387821

Effect of Buffer Conditions and Organic Cosolvents on the Rate of Strain-Promoted Azide-Alkyne Cycloaddition.

Derek L Davis1, Erin K Price1, Sabrina O Aderibigbe1, Maureen X-H Larkin1, Emmett D Barlow1, Renjie Chen1, Lincoln C Ford1, Zackery T Gray1, Stephen H Gren1, Yuwei Jin1, Keith S Keddington1, Alexandra D Kent1, Dasom Kim1, Ashley Lewis1, Rami S Marrouche1, Mark K O'Dair1, Daniel R Powell1, Mick'l H C Scadden1, Curtis B Session1, Jifei Tao1, Janelle Trieu1, Kristen N Whiteford1, Zheng Yuan1, Goyeun Yun1, Judy Zhu1, Jennifer M Heemstra1.   

Abstract

We investigate the effect of buffer identity, ionic strength, pH, and organic cosolvents on the rate of strain-promoted azide-alkyne cycloaddition with the widely used DIBAC cyclooctyne. The rate of reaction between DIBAC and a hydrophilic azide is highly tolerant to changes in buffer conditions but is impacted by organic cosolvents. Thus, bioconjugation reactions using DIBAC can be carried out in the buffer that is most compatible with the biomolecules being labeled, but the use of organic cosolvents should be carefully considered.

Entities:  

Year:  2016        PMID: 27387821     DOI: 10.1021/acs.joc.6b01112

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

1.  Fluorine-18 labeling of an anti-HER2 VHH using a residualizing prosthetic group via a strain-promoted click reaction: Chemistry and preliminary evaluation.

Authors:  Zhengyuan Zhou; Satish K Chitneni; Nick Devoogdt; Michael R Zalutsky; Ganesan Vaidyanathan
Journal:  Bioorg Med Chem       Date:  2018-03-15       Impact factor: 3.641

2.  Collaborating with Undergraduates To Contribute to Biochemistry Community Resources.

Authors:  Kathryn L Haas; Jennifer M Heemstra; Marnix H Medema; Louise K Charkoudian
Journal:  Biochemistry       Date:  2017-11-02       Impact factor: 3.162

3.  Live Monitoring of Strain-Promoted Azide Alkyne Cycloadditions in Complex Reaction Environments by Inline ATR-IR Spectroscopy.

Authors:  Dennis Svatunek; Gottfried Eilenberger; Christoph Denk; Daniel Lumpi; Christian Hametner; Günter Allmaier; Hannes Mikula
Journal:  Chemistry       Date:  2020-03-13       Impact factor: 5.236

4.  Multi-Institution Research and Education Collaboration Identifies New Antimicrobial Compounds.

Authors:  Amelia A Fuller; Amy B Dounay; Douglas Schirch; Daniel G Rivera; Karl A Hansford; Alysha G Elliott; Johannes Zuegg; Matthew A Cooper; Mark A T Blaskovich; Jacob R Hitchens; Sarah Burris-Hiday; Kristiana Tenorio; Yanira Mendez; J Geno Samaritoni; Martin J O'Donnell; William L Scott
Journal:  ACS Chem Biol       Date:  2020-11-26       Impact factor: 5.100

  4 in total

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