3.4.22.6 2,4-dichlorocyclohexan-1-one + cyclohexanone yield: 43%, 80:20 anti/syn, ee (anti): 81% 3.4.22.6 2,6-dichlorocyclohexan-1-one + cyclohexanone yield: 39%, 99:01 anti/syn, ee (anti): 58% 3.4.22.6 2-chlorocyclohexan-1-one + cyclohexanone yield: 30%, 86:14 anti/syn, ee (anti): 79% 3.4.22.6 2-nitrocyclohexan-1-one + cyclohexanone yield: 24%, 87:13 anti/syn, ee (anti): 82% 3.4.22.6 3-chlorocyclohexan-1-one + cyclohexanone yield: 32%, 65:35 anti/syn, ee (anti): 93% 3.4.22.6 3-nitrocyclohexan-1-one + cyclohexanone yield: 41%, 87:13 anti/syn, ee (anti): 86% 3.4.22.6 4-bromocyclohexan-1-one + cyclohexanone yield: 29%, 81:19 anti/syn, ee (anti): 84% 3.4.22.6 4-chlorocyclohexan-1-one + cyclohexanone yield: 47%, 69:31 anti/syn, ee (anti): 75% 3.4.22.6 4-cyanobenzaldehyde + cyclohexanone catalytic activity and stereoselectivity of chymopapainare influenced by different media. Best catalytic activity and moderate stereoselectivity in DMSO (yield: 50%, anti/syn ratio 55:45, ee(anti): 40%), best enantioselectivity in CH2Cl2 (yield: 18%, anti/syn ratio: 61:39, ee(anti): 79%) 3.4.22.6 4-cyanobenzaldehyde + cyclohexanone solvent: water/MeCN. The water content greatly affects the activity and selectivity of chymopapain for the aldol reaction. The best enantioselectivity and diastereoselectivity at the water content of 0.12 (water/MeCN, v/v), which give the product in a yield of 28% with 73:27 (anti/syn ratio) and 77% ee (for anti isomer). Best enzyme activity at the water content of 0.15, which give a yield of 32% with lower selectivity 3.4.22.6 4-cyanocyclohexan-1-one + cyclohexanone yield: 60%, 72:28 anti/syn, ee (anti): 76% 3.4.22.6 4-methylcyclohexan-1-one + cyclohexanone yield: 23%, 63:37 anti/syn, ee (anti): 96% 3.4.22.6 4-nitrocyclohexan-1-one + acetaldehyde yield: 12%, ee (anti): 14% 3.4.22.6 4-nitrocyclohexan-1-one + cycloheptanone yield: 19%, 47:53 anti/syn, ee (anti): 26% 3.4.22.6 4-nitrocyclohexan-1-one + cyclohexanone yield: 69%, 63:37 anti/syn, ee (anti): 78% 3.4.22.6 4-nitrocyclohexan-1-one + cyclopentanone yield: 73%, 56:44 anti/syn, ee (anti): 52% 3.4.22.6 furan-2-carbaldehyde + cyclohexanone yield: 16%, 63:37 anti/syn, ee (anti): 61% 3.4.22.6 additional information mass spectroscopy studies show unequivocally the specificity of chymopapain toward Ala, Pro, Val and Lys for positions P4 to P1 while not presenting high specificity for residues in position P1