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Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

Anne-Katrin Späte, Verena F. Schart, Julia Häfner, Andrea Niederwieser, Thomas U. Mayer and Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242. https://doi.org/10.3762/bjoc.10.232

Supporting Information

Additional MOE experiments and ¹H and ¹³C NMR spectra of Ac₄GlcNCyoc (1) and Ac₄GalNCyoc (2).

Supporting Information File 1: Additional MOE experiments and NMR spectra.
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Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

Anne-Katrin Späte, Verena F. Schart, Julia Häfner, Andrea Niederwieser, Thomas U. Mayer and Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242. https://doi.org/10.3762/bjoc.10.232

How to Cite

Späte, A.-K.; Schart, V. F.; Häfner, J.; Niederwieser, A.; Mayer, T. U.; Wittmann, V. Beilstein J. Org. Chem. 2014, 10, 2235–2242. doi:10.3762/bjoc.10.232

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Dube, D. H.; Williams, D. A. Handbook of In Vivo Chemistry in Mice; Wiley, 2019; pp 209–248. doi:10.1002/9783527344406.ch8
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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)