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. Author manuscript; available in PMC: 2023 Apr 15.
Published in final edited form as: J Org Chem. 2022 Mar 30;87(8):5076–5084. doi: 10.1021/acs.joc.1c02931

Table 1.

Photolysis (5 mW LED at 365 nm) of alkyl-Cbls in phosphate buffered saline.

ß-axial Substituent K OW a k (s−1)b Φc
3 methyl 1.09 0.10 ± 0.01 0.35 ± 0.02
4 ethyl 1.33 0.13 ± 0.02 0.44 ± 0.05
5 propyl 1.75 0.087 ± 0.006 0.31 ± 0.02
6 isobutyl 2.08 0.084 ± 0.007 0.29 ± 0.02
7 decyl 4.67 0.04 ± 0.02 0.14 ± 0.06
8 cyclopropyl 1.25 0.026 ± 0.003 0.09 ± 0.01
9 cyclopropylmethyl 1.58 0.099 ± 0.004 0.34 ± 0.01
10 cyclobutyl 1.67 0.064 ± 0.006 0.22 ± 0.02
11 cyclobutylmethyl 2.00 0.083 ± 0.006 0.29 ± 0.01
12 cyclohexylmethyl 2.83 0.045 ± 0.004 0.16 ± 0.01
13 1-aminopropyl 0.17 0.079 ± 0.002 0.27 ± 0.01
14 1-carboxyethyl 0.35 0.10 ± 0.01 0.34 ± 0.05
15 1-amino-1-carboxypropyl -0.41 0.066 ± 0.005 0.23 ± 0.02
16 1-methoxy-1-oxopentyl 1.44 0.074 ± 0.008 0.26 ± 0.03
17 1-carboxypentyl 1.60 0.07 ± 0.01 0.23 ± 0.04
18 1-amino-1-oxohexyl 0.95 0.07 ± 0.01 0.23 ± 0.04
a

The octanol water partition coefficient was calculated using ChemDraw 20.0.

b

Photolysis rate from the average of three trials per conjugate.

c

The quantum yields were calculated using methyl-Cbl as the actinometer.38