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Literature summary extracted from
- Chymopapain-catalyzed direct asymmetric aldol reaction (2012), Adv. Synth. Catal., 354, 712-719.
No PubMed abstract available
Natural Substrates/ Products (Substrates)
| EC Number | Natural Substrates | Organism | Comment (Nat. Sub.) | Natural Products | Comment (Nat. Pro.) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 3.4.22.6 | 2,4-dichlorocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 43%, 80:20 anti/syn, ee (anti): 81% | ? | - |
? |  |
| 3.4.22.6 | 2,6-dichlorocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 39%, 99:01 anti/syn, ee (anti): 58% | ? | - |
? | |
| 3.4.22.6 | 2-chlorocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 30%, 86:14 anti/syn, ee (anti): 79% | ? | - |
? | |
| 3.4.22.6 | 2-nitrocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 24%, 87:13 anti/syn, ee (anti): 82% | ? | - |
? | |
| 3.4.22.6 | 3-chlorocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 32%, 65:35 anti/syn, ee (anti): 93% | ? | - |
? | |
| 3.4.22.6 | 3-nitrocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 41%, 87:13 anti/syn, ee (anti): 86% | ? | - |
? | |
| 3.4.22.6 | 4-bromocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 29%, 81:19 anti/syn, ee (anti): 84% | ? | - |
? | |
| 3.4.22.6 | 4-chlorocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 47%, 69:31 anti/syn, ee (anti): 75% | ? | - |
? | |
| 3.4.22.6 | 4-cyanobenzaldehyde + cyclohexanone | Carica papaya | 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%) | 4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile | - |
? | |
| 3.4.22.6 | 4-cyanobenzaldehyde + cyclohexanone | Carica papaya | 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 | 4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile | - |
? | |
| 3.4.22.6 | 4-cyanocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 60%, 72:28 anti/syn, ee (anti): 76% | ? | - |
? | |
| 3.4.22.6 | 4-methylcyclohexan-1-one + cyclohexanone | Carica papaya | yield: 23%, 63:37 anti/syn, ee (anti): 96% | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + acetaldehyde | Carica papaya | yield: 12%, ee (anti): 14% | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + cycloheptanone | Carica papaya | yield: 19%, 47:53 anti/syn, ee (anti): 26% | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + cyclohexanone | Carica papaya | yield: 69%, 63:37 anti/syn, ee (anti): 78% | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + cyclopentanone | Carica papaya | yield: 73%, 56:44 anti/syn, ee (anti): 52% | ? | - |
? | |
| 3.4.22.6 | furan-2-carbaldehyde + cyclohexanone | Carica papaya | yield: 16%, 63:37 anti/syn, ee (anti): 61% | ? | - |
? | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 3.4.22.6 | Carica papaya | P14080 | - |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 3.4.22.6 | 2,4-dichlorocyclohexan-1-one + cyclohexanone | yield: 43%, 80:20 anti/syn, ee (anti): 81% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 2,6-dichlorocyclohexan-1-one + cyclohexanone | yield: 39%, 99:01 anti/syn, ee (anti): 58% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 2-chlorocyclohexan-1-one + cyclohexanone | yield: 30%, 86:14 anti/syn, ee (anti): 79% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 2-nitrocyclohexan-1-one + cyclohexanone | yield: 24%, 87:13 anti/syn, ee (anti): 82% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 3-chlorocyclohexan-1-one + cyclohexanone | yield: 32%, 65:35 anti/syn, ee (anti): 93% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 3-nitrocyclohexan-1-one + cyclohexanone | yield: 41%, 87:13 anti/syn, ee (anti): 86% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 4-bromocyclohexan-1-one + cyclohexanone | yield: 29%, 81:19 anti/syn, ee (anti): 84% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 4-chlorocyclohexan-1-one + cyclohexanone | yield: 47%, 69:31 anti/syn, ee (anti): 75% | Carica papaya | ? | - |
? | |
| 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%) | Carica papaya | 4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile | - |
? | |
| 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 | Carica papaya | 4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile | - |
? | |
| 3.4.22.6 | 4-cyanocyclohexan-1-one + cyclohexanone | yield: 60%, 72:28 anti/syn, ee (anti): 76% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 4-methylcyclohexan-1-one + cyclohexanone | yield: 23%, 63:37 anti/syn, ee (anti): 96% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + acetaldehyde | yield: 12%, ee (anti): 14% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + cycloheptanone | yield: 19%, 47:53 anti/syn, ee (anti): 26% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + cyclohexanone | yield: 69%, 63:37 anti/syn, ee (anti): 78% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | 4-nitrocyclohexan-1-one + cyclopentanone | yield: 73%, 56:44 anti/syn, ee (anti): 52% | Carica papaya | ? | - |
? | |
| 3.4.22.6 | furan-2-carbaldehyde + cyclohexanone | yield: 16%, 63:37 anti/syn, ee (anti): 61% | Carica papaya | ? | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 3.4.22.6 | Chymopapain | - |
Carica papaya |
Temperature Optimum [°C]
| EC Number | Temperature Optimum [°C] | Temperature Optimum Maximum [°C] | Comment | Organism |
|---|---|---|---|---|
| 3.4.22.6 | additional information | - |
temperature is an important factor affecting the enzyme stability, selectivity and reaction rate | Carica papaya |
| 3.4.22.6 | 25 | - |
assay at | Carica papaya |
| 3.4.22.6 | 30 | - |
best diastereoselectivity and enantioselectivity is reached at 30°C, which give a yield of 27% with 76:24 (anti/syn ratio) and 78% ee (for anti isomer) | Carica papaya |
| 3.4.22.6 | 40 | - |
highest activity for aldol reaction | Carica papaya |
pH Optimum
| EC Number | pH Optimum Minimum | pH Optimum Maximum | Comment | Organism |
|---|---|---|---|---|
| 3.4.22.6 | additional information | - |
pH value of the reaction medium plays a significant role in maintaining the stability and catalytic activity of the enzyme | Carica papaya |
| 3.4.22.6 | 4.91 | - |
assay at. Chymopapain shows the best activity and enantioselectivity in the presence of phosphate buffer (pH 4.91, buffer/MeCN:0.12, v/v), which give the product in yield of 45% with 72:28 (anti/syn ratio) and 78% ee (for anti isomer) | Carica papaya |
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