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. Author manuscript; available in PMC: 2015 Sep 18.
Published in final edited form as: Chem Biol. 2014 Sep 18;21(9):1075–1101. doi: 10.1016/j.chembiol.2014.09.002

Table 3.

Recent developments in bioconjugation at Arg, Met, Trp and Tyr residues.

Entry Residue Reagent(s) Product Reference
1 Arg graphic file with name nihms626240t38.jpg graphic file with name nihms626240t39.jpg (Gauthier and Klok, 2011)
2 Met graphic file with name nihms626240t40.jpg graphic file with name nihms626240t41.jpg (Kramer and Deming, 2012)
3 Trp graphic file with name nihms626240t42.jpg
Rh2(OAc)4, t-BuNHOH pH 6.0
graphic file with name nihms626240t43.jpg (Antos and Francis, 2004; Antos et al., 2009)
4 Tyr graphic file with name nihms626240t44.jpg
Pd(OAc)2 (40 μM)
TPPTS (0.48 mM)
pH 8.5–9
graphic file with name nihms626240t45.jpg (Chen et al., 2009; Tilley and Francis, 2006)
5 Tyr
  1. graphic file with name nihms626240t46.jpg

    pH 9, 4 °C, 15 min

  2. Na2S2O4 (100 mM)

    pH 7.2, r.t., 2 h

  3. NalO4

  4. graphic file with name nihms626240t47.jpg

graphic file with name nihms626240t48.jpg (Hooker et al., 2004)
6 Tyr
  1. graphic file with name nihms626240t49.jpg

    pH 9, 4 °C, 15 min

  2. graphic file with name nihms626240t50.jpg

    pH 6, r.t., 2 h

graphic file with name nihms626240t51.jpg (Gavrilyuk et al., 2013; Schlick et al., 2005)
7 Tyr graphic file with name nihms626240t52.jpg
pH 6.5, r.t., 18 h
graphic file with name nihms626240t53.jpg (Joshi et al., 2004; McFarland et al., 2008; Romanini and Francis, 2007)
8 Tyr graphic file with name nihms626240t54.jpg graphic file with name nihms626240t55.jpg (Ban et al., 2010; Ban et al., 2013; Jessica et al., 2013)
9 Tyr graphic file with name nihms626240t56.jpg
Ni(OAc)2, Gly-Gly-His
MMPP, pH 7
graphic file with name nihms626240t57.jpg (Kodadek et al., 2005; Meunier et al., 2004)
10 Tyr graphic file with name nihms626240t58.jpg
[Ru(bpy)3]Cl2, (NH4)2S2O8
graphic file with name nihms626240t59.jpg (Sato and Nakamura, 2013)
11 Tyr graphic file with name nihms626240t60.jpg
(NH4)2Ce(NO3)6
pH 6, 1 h, r.t.
graphic file with name nihms626240t61.jpg (Sato and Nakamura, 2013; Seim et al., 2011)
12 Tyr
  1. IPyBF4, H2O;

  2. Pd(OAc)2, TPPTS

    K3PO4, ArBF3, H2O

graphic file with name nihms626240t62.jpg (Vilaró et al., 2008)
13 Tyr
  1. Tyrosinase, O2

  2. graphic file with name nihms626240t63.jpg

graphic file with name nihms626240t64.jpg (Long and Hedstrom, 2012)