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Literature summary for 3.4.22.3 extracted from

  • Fu, J.; Gao, N.; Yang, Y.; Guan, Z.; He, Y.
    Ficin-catalyzed asymmetric aldol reactions of heterocyclic ketones with aldehydes (2013), J. Mol. Catal. B, 97, 1-4.
No PubMed abstract available
Search for more literature for 3.4.22.3

Organism

Organism UniProt Comment Textmining
Ficus carica
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1-methylpiperidin-4-one + 4-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 44%, 19:81 anti/syn ratio, enantioselectivity: 5%/1% (anti/syn) Ficus carica ?
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 ?
cyclohexanone + 3-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 39%, 86:14 anti/syn ratio, enantioselectivity: 81%/14% (anti/syn) Ficus carica ?
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 ?
cyclohexanone + 4-cyanobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 21%, 79:21 anti/syn ratio, enantioselectivity: 77%/5% (anti/syn) Ficus carica ?
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 ?
oxan-2-one + 4-bromobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 29%, 77:23 anti/syn ratio, enantioselectivity: 71%/27% (anti/syn) Ficus carica ?
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 ?
oxan-2-one + 4-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 21%, 42:58 anti/syn ratio, enantioselectivity: 60%/24% (anti/syn) Ficus carica ?
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 ?
oxan-3-one + 4-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 28%, 54:46 anti/syn ratio, enantioselectivity: 57%/28% (anti/syn) Ficus carica ?
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 ?
oxan-4-one + 4-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 31%, 53:47 anti/syn ratio, enantioselectivity: 25%/17% (anti/syn) Ficus carica ?
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 ?
tert-butyl 4-oxopiperidine-1-carboxylate + 3-bromobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 25%, 47:53 anti/syn ratio, enantioselectivity: 51%/45% (anti/syn) Ficus carica ?
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 ?
tert-butyl 4-oxopiperidine-1-carboxylate + 3-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 29%, 51:49 anti/syn ratio, enantioselectivity: 59%/45% (anti/syn) Ficus carica ?
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 ?
tert-butyl 4-oxopiperidine-1-carboxylate + 4-bromobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 35%, 75:25 anti/syn ratio, enantioselectivity: 67%/36% (anti/syn) Ficus carica ?
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 ?
tert-butyl 4-oxopiperidine-1-carboxylate + 4-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 36%, 41:59 anti/syn ratio, enantioselectivity: 60%/14% (anti/syn) Ficus carica tert-butyl 3-[hydroxy(4-nitrophenyl)methyl]-4-oxopiperidine-1-carboxylate
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 ?
tert-butyl 4-oxopiperidine-1-carboxylate + 4-nitrobenzaldehyde the catalytic activity and stereoselectivity of ficin are significantly influenced by reaction media. Best yield of 34% with a poor enantioselectivity of 29% in THF. Best enantioselectivity of 57% with a yield of 28% in MeCN. In tested polar solvents including i-PrOH, DMSO, and DMF, ficin shows lower activityand enantioselectivity Ficus carica tert-butyl 3-[hydroxy(4-nitrophenyl)methyl]-4-oxopiperidine-1-carboxylate
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 ?
tert-butyl 4-oxopiperidine-1-carboxylate + 4-nitrobenzaldehyde water content is important for enantioselectivity and enzymatic activity. When water content is at 0.15 (H2O/(H2O+MeCN): 0.15,v/v) the reaction give the best enantioselectivity of 59% with 32% yield Ficus carica tert-butyl 3-[hydroxy(4-nitrophenyl)methyl]-4-oxopiperidine-1-carboxylate
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 ?
thian-4-one + 3-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 26%, 86:14 anti/syn ratio, enantioselectivity: 77%/1% (anti/syn) Ficus carica ?
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 ?
thian-4-one + 4-cyanobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 23%, 84:16 anti/syn ratio, enantioselectivity: 76%/53% (anti/syn) Ficus carica ?
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 ?
thiolan-3-one + 4-nitrobenzaldehyde reaction condition: 30°C, MeCN (0.85 mL) and deionized water (0.15 mL). Yield: 31%, 40:60 anti/syn ratio, enantioselectivity: 45%/23% (anti/syn) Ficus carica ?
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 ?

Synonyms

Synonyms Comment Organism
ficin
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 Ficus carica

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
25
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 assay at Ficus carica
30
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 best enantioselectivity of 60% at 30°C Ficus carica