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. 2018 Jul 25;9(35):7053–7057. doi: 10.1039/c8sc02513d

Table 1. Cu2+-nitrile-mediated activation of A′3P and effect of Gly or GlyGly.

Inline graphic
Entry Nitrile R Yield of 3 or 2′-transfer adducts a (%)
CuCl2
CuCl2 and Gly
CuCl2 and GlyGly
3 b 2′-adduct 3 b 2′-adduct 3 b 2′-adduct
1 1 graphic file with name c8sc02513d-u2.jpg 84 n.d. c 85 d n.d. 80 n.d.
2 4 graphic file with name c8sc02513d-u3.jpg n.d. n.d. n.d. n.d. n.d. n.d.
3 5 graphic file with name c8sc02513d-u4.jpg n.d. n.d. n.d. n.d. n.d. n.d.
4 6 graphic file with name c8sc02513d-u5.jpg 5 n.d. 2 n.d. n.d. n.d.
5 7 graphic file with name c8sc02513d-u6.jpg 24 15 21 8 23 5.4
6 8 graphic file with name c8sc02513d-u7.jpg 53 6 50 4 97 e 3
7 10 graphic file with name c8sc02513d-u8.jpg 75 n.d. 60 n.d. 5 n.d.
8 11 graphic file with name c8sc02513d-u9.jpg 35 n.d. 22 n.d. 34 n.d.

aStandard reaction conditions: nitrile (100 mM), 2 (50 mM), CuCl2 (25 mM) and Gly or GlyGly (50 mM) in 90% H2O, 10% D2O at pH 4 (entries 1, 5 and 8) or pH 5.5 (entries 2, 3, 4, 6 and 7), heated at 40 °C for 20 hours.

bInferred from the amount of 3 plus adenosine 2′-phosphate A2′P 12, assuming that when 3 hydrolyses it always gives 2 and 12 in 1.8 : 1 ratios.17

cNot detected.

dInitial pH 5.5.

eInitial pH 4.