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

Authors :
Davis DL
Price EK
Aderibigbe SO
Larkin MX
Barlow ED
Chen R
Ford LC
Gray ZT
Gren SH
Jin Y
Keddington KS
Kent AD
Kim D
Lewis A
Marrouche RS
O'Dair MK
Powell DR
Scadden MH
Session CB
Tao J
Trieu J
Whiteford KN
Yuan Z
Yun G
Zhu J
Heemstra JM
Source :
The Journal of organic chemistry [J Org Chem] 2016 Aug 05; Vol. 81 (15), pp. 6816-9. Date of Electronic Publication: 2016 Jul 14.
Publication Year :
2016

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.

Details

Language :
English
ISSN :
1520-6904
Volume :
81
Issue :
15
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
27387821
Full Text :
https://doi.org/10.1021/acs.joc.6b01112