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. Author manuscript; available in PMC: 2015 Aug 7.
Published in final edited form as: J Am Chem Soc. 2015 May 5;137(19):6232–6244. doi: 10.1021/ja5132648

Table 1. Scope.

Entry HaloTag-
targetable
caged
precursor		 Delivered
reactive
electrophiles
(alkyne-functionalized)a 		% Delivery
efficiency
in live cellsb
1 Ht-Pre-HNE
17 		graphic file with name nihms-711351-t0012.jpg HNE(alkyne)
1 		33 ± 2
2 Ht-Pre-ONE
11 		graphic file with name nihms-711351-t0013.jpg ONE(alkyne)
2 		– c
3 Ht-Pre-dHNE
12 		graphic file with name nihms-711351-t0014.jpg dHNE(alkyne)
3 		21 ± 2
4 Ht-Pre-HHE
13 		graphic file with name nihms-711351-t0015.jpg HHE(alkyne)
4 		30 ± 1
5 Ht-Pre-HDE
14 		graphic file with name nihms-711351-t0016.jpg HDE(alkyne)
5 		29 ± 1
6 Ht-Pre-HDDE
15 		graphic file with name nihms-711351-t0017.jpg HDDE(alkyne)
6 		– c
7 Ht-Pre-2-HD
16 		graphic file with name nihms-711351-t0018.jpg 2-HD(alkyne)
7 		– c
8 Ht-Pre-DE
21 		graphic file with name nihms-711351-t0019.jpg DE(alkyne)
8 		22 ± 2
9 Ht-Pre-CHE
22 		graphic file with name nihms-711351-t0020.jpg CHE(alkyne)
9 		25 ± 1
10 Ht-Pre-CPE
23 		graphic file with name nihms-711351-t0021.jpg CPE(alkyne)
10 		19 ± 2
a

Racemic where applicable.

b

Error range is S.D. (n = 6). See also Figure 6 and S2.

c

Not determined (see discussion in text).