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. Author manuscript; available in PMC: 2021 Apr 24.
Published in final edited form as: J Nat Prod. 2020 Mar 20;83(4):937–954. doi: 10.1021/acs.jnatprod.9b00773

Table 2.

Stability of BAPCs and Their Cleavage by NADPH-Cytochrome P450 Oxidoreductase

compound percent BAPC hydrolysi s/cl eavage (non-enzymatic) in phosphate buffer (pH 7.4, 48 h) percent BAPC cleavage by POR (90 min)
22 0.25 NCa
23 0.84 13.5
24 1.59 1.1
25 0.69 3.8
26 4.03 7.6
35 0 NC
36 0 NC
37 0b 14.2
(24% cyclization of 37 to 35)
38 0.5c 5.6
(48% cyclization of 38 to 36)
39 0b 17.9
(46% cyclization of 39 to 35)
40 0c 25.5
(35% cyclization of 40 to 36)
41 100 100
43 0.35 2.7
44 ND 4.1
45 0.69 25.4
a

NC= no cleavage observed.

b

significant cyclization to 35.

c

significant cyclization to 36.