. Author manuscript; available in PMC: 2020 Feb 27.

Published in final edited form as: Chemistry. 2018 Mar 27;24(23):6030–6035. doi: 10.1002/chem.201705771

Table 2.

Percent yield of monoadducts and crosslink adducts formed in the two-step crosslinking reactions with DMC. ND: non detected. NA: non available.

Oligonucleotide	Alkylation step	9a	9b	R 9b/9a	10a	10b	Crosslinking efficiency
11 (GpC)	first	0.54 (±0.04)	0.98 (±0.04)	1.8 (±0.07)	ND	ND	NA
	second	0.31 (±0.2)	1.20 (±0.6)	4.2 (±0.6)	ND	0.60 (±0.4)	33%
12 (GpC)	first	0.50 (±0.02)	1.52 (±0.07)	3.10 (±0.04)	ND	ND	NA
	second	0.12 (±0.02)	0.80 (±0.02)	6.90 (±1)	ND	0.40 (±0.09)	33%
13 (CpG)	first	0.92 (±0.2)	0.19 (±0.04)	0.21 (±0.06)	ND	ND	NA
	second	0.11 (±0.02)	0.13 (±0.01)	1.13 (±0.3)	0.50 (±0.2)	ND	82%
14 (CpG)	first	1.1 (±0.07)	0.88 (±0.08)	0.8 (±0.07)	ND	ND	NA
	second	0.14 (±0.001)	0.70 (±0.03)	4.90 (±0.2)	0.76 (±0.01)	ND	84%