Biomimetic Modeling of Copper Complexes: A Study of Enantioselective Catalytic Oxidation on 𝐷-(+)-Catechin and 𝐿-(−)-Epicatechin with Copper Complexes

Table 1

Kinetic parameters for the stereoselective oxidations of 𝐷-(+)-catechin and 𝐿-(–)-epicatechin in methanol-aqueous phosphate buffer, pH 7.0 at 20±0.1^∘C.

Complexes	𝐾M(M)	𝑘cat(s^−1)	𝑘cat/𝐾M(M^−1s^−1)	𝑅%
Substrate
[Cu2(𝑅-DABN-4Bz4)]^4+
𝐷-(+)-catechin	(2.00±0.33)×10^−5	(1.21±0.75)×10^−2	604	−32.0
𝐿-(–)-epicatechin	(1.20±0.31)×10^−5	(1.41±0.96)×10^−2	1169
[Cu3(𝑅-DABN-4Bz4)]^6+
𝐷-(+)-catechin	(1.33±0.32)×10^−5	(1.85±0.12)×10^−2	1387	32.8
𝐿-(–)-epicatechin	(3.93±0.94)×10^−5	(2.75±0.31)×10^−2	701
[Cu2(𝐿-Lys-4Bz4)]^4+
𝐷-(+)-catechin	(1.14±0.38)×10^−5	(1.86±0.18)×10^−2	1632	46.0
𝐿-(–)-epicatechin	(2.95±0.75)×10^−5	(1.78±0.17)×10^−2	604
[Cu3(𝐿-Lys-4Bz4)]^6+
𝐷-(+)-catechin	(1.37±0.33)×10^−5	(2.01±0.02)×10^−2	1470	60.4
𝐿-(–)-epicatechin	(1.02±0.26)×10^−4	(3.71±0.58)×10^−2	363
[Cu2(𝑅-DABN-3Im4)]^4+
𝐷-(+)-catechin	(2.19±0.70)×10^−5	(1.09±0.15)×10^−2	498	7.2
𝐿-(–)-epicatechin	(1.96±0.58)×10^−5	(8.44±0.69)×10^−3	431
[Cu3(𝑅-DABN-3Im4)]^6+
𝐷-(+)-catechin	(1.01±0.32)×10^−5	(5.10±0.39)×10^−3	507	42.6
𝐿-(–)-epicatechin	(3.51±1.05)×10^−5	(7.15±0.80)×10^−3	204
[Cu2(𝑅-DABN-𝐿-Ala-Bz4)]^4+
𝐷-(+)-catechin	(3.60±0.36)×10^−5	(2.77±0.11)×10^−2	769	8.8
𝐿-(–)-epicatechin	(4.81±0.37)×10^−5	(3.10±0.11)×10^−2	644
[Cu3(𝑅-DABN-𝐿-Ala-Bz4)]^6+
𝐷-(+)-catechin	(5.05±0.48)×10^−5	(6.46±0.15)×10^−2	1280	5.3
𝐿-(–)-epicatechin	(5.08±0.37)×10^−5	(5.84±0.10)×10^−2	1150
[Cu2(L66)]^4+
𝐷-(+)-catechin	(6.69±1.06)×10^−5	(7.57±0.60)×10^−2	1131	1.9
𝐿-(–)-epicatechin	(4.08±0.81)×10^−5	(4.44±0.13)×10^−2	1088