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2,4-dichlorocyclohexan-1-one + cyclohexanone
?
yield: 43%, 80:20 anti/syn, ee (anti): 81%
-
-
?
2,6-dichlorocyclohexan-1-one + cyclohexanone
?
yield: 39%, 99:01 anti/syn, ee (anti): 58%
-
-
?
2-chlorocyclohexan-1-one + cyclohexanone
?
yield: 30%, 86:14 anti/syn, ee (anti): 79%
-
-
?
2-nitrocyclohexan-1-one + cyclohexanone
?
yield: 24%, 87:13 anti/syn, ee (anti): 82%
-
-
?
3-chlorocyclohexan-1-one + cyclohexanone
?
yield: 32%, 65:35 anti/syn, ee (anti): 93%
-
-
?
3-nitrocyclohexan-1-one + cyclohexanone
?
yield: 41%, 87:13 anti/syn, ee (anti): 86%
-
-
?
4-bromocyclohexan-1-one + cyclohexanone
?
yield: 29%, 81:19 anti/syn, ee (anti): 84%
-
-
?
4-chlorocyclohexan-1-one + cyclohexanone
?
yield: 47%, 69:31 anti/syn, ee (anti): 75%
-
-
?
4-cyanobenzaldehyde + cyclohexanone
4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile
4-cyanocyclohexan-1-one + cyclohexanone
?
yield: 60%, 72:28 anti/syn, ee (anti): 76%
-
-
?
4-methylcyclohexan-1-one + cyclohexanone
?
yield: 23%, 63:37 anti/syn, ee (anti): 96%
-
-
?
4-nitrocyclohexan-1-one + acetaldehyde
?
yield: 12%, ee (anti): 14%
-
-
?
4-nitrocyclohexan-1-one + cycloheptanone
?
yield: 19%, 47:53 anti/syn, ee (anti): 26%
-
-
?
4-nitrocyclohexan-1-one + cyclohexanone
?
yield: 69%, 63:37 anti/syn, ee (anti): 78%
-
-
?
4-nitrocyclohexan-1-one + cyclopentanone
?
yield: 73%, 56:44 anti/syn, ee (anti): 52%
-
-
?
Albumin + H2O
?
-
-
-
-
?
azocasein + H2O
?
-
-
-
-
?
benzoyl-Gly amide + H2O
benzoyl-Gly + NH3
-
weak activity
-
-
?
benzoyl-L-argininamide + H2O
N-benzoyl-Arg + NH3
-
-
-
-
?
benzyloxycarbonyl-Lys phenyl ester + H2O
benzyloxycarbonyl + phenol
-
-
-
-
?
benzyloxycarbonyl-Phe-Arg-4-methylcoumarin 7-amide + H2O
benzyloxycarbonyl-Phe-Arg-4-methylcoumarin 7-amide
-
-
-
-
?
carbobenzoxy-L-Glu-L-Tyr + H2O
Carbobenzoxy-Glu + Tyr
-
weak activity
-
-
?
furan-2-carbaldehyde + cyclohexanone
?
yield: 16%, 63:37 anti/syn, ee (anti): 61%
-
-
?
Hemoglobin + H2O
?
-
-
-
-
?
L-Leu amide + H2O
Leu + NH3
-
weak activity
-
-
?
L-Leu-L-Tyr + H2O
Leu + Tyr
-
weak activity
-
-
?
methyl red-Abu-Ala-Pro-Val-Lys-Lys(N5-(5-carboxyfluorescein))-NH2 + H2O
methyl red-Abu-Ala-Pro-Val-Lys + Lys(N5-(5-carboxyfluorescein))-NH2
methyl red-Abu-Ser-Ala-Pro-Val-Lys-Ala-Lys(N5-(5-carboxyfluorescein))-NH2 + H2O
methyl red-Abu-Ser-Ala-Pro-Val-Lys + Ala-Lys(N5-(5-carboxyfluorescein))-NH2
-
pH 6.2 or pH 7.4, 10 min, 37°C
-
-
?
methyl red-Abu-Ser-Ala-Pro-Val-Lys-Ala-Lys(N6-(5-carboxyfluorescein))-NH2 + H2O
methyl red-Abu-Ser-Ala-Pro-Val-Lys + Ala-Lys(N6-(5-carboxyfluorescein))-NH2
-
FRET 1, fluorescence resonance energy transfer peptide 1
-
-
?
N,N-diBoc-dityrosine-(isoniacid)2 + H2O
N,N-diBoc-dityrosine + 2 isoniacid
-
-
-
?
N-acetyl-L-Phe-L-Tyr + H2O
?
-
weak activity
-
-
?
N-alpha-benzoyl-DL-arginine-p-nitroanilide + H2O
N-alpha-benzoyl-DL-arginine + p-nitroaniline
-
-
-
-
?
N-alpha-benzoyl-DL-arginine-para-nitroanilide + H2O
?
-
-
-
-
?
N-alpha-benzoyl-L-arginine ethyl ester + H2O
?
-
-
-
-
?
N-alpha-benzoylphenylalanine-arginine-4-methylcoumarin-7-amide + H2O
?
-
-
-
-
?
N-benzoyl-Arg-4-nitroanilide + H2O
N-benzoyl-Arg + 4-nitroaniline
N-benzoyl-L-Arg ethyl ester + H2O
N-benzoyl-Arg + ethanol
-
-
-
-
?
N-benzyloxycarbonyl-Gly p-nitrophenyl ester + H2O
N-benzyloxycarbonyl-Gly + p-nitrophenol
-
-
-
-
?
N-tosyl-L-Arg methyl ester + H2O
N-tosyl-Arg + methanol
-
-
-
-
?
succinyl-albumin
?
-
-
-
-
?
succinyl-Phe-Arg-p-nitroanilide + H2O
succinyl-Phe-Arg + p-nitroaniline
-
mechanism of action
-
-
?
additional information
?
-
4-cyanobenzaldehyde + cyclohexanone
4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile
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-cyanobenzaldehyde + cyclohexanone
4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile
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
-
-
?
methyl red-Abu-Ala-Pro-Val-Lys-Lys(N5-(5-carboxyfluorescein))-NH2 + H2O
methyl red-Abu-Ala-Pro-Val-Lys + Lys(N5-(5-carboxyfluorescein))-NH2
-
FRET 2, fluorescence resonance energy transfer peptide 2
-
-
?
methyl red-Abu-Ala-Pro-Val-Lys-Lys(N5-(5-carboxyfluorescein))-NH2 + H2O
methyl red-Abu-Ala-Pro-Val-Lys + Lys(N5-(5-carboxyfluorescein))-NH2
-
pH 6.2 or pH 7.4, 10 min, 37°C
-
-
?
N-benzoyl-Arg-4-nitroanilide + H2O
N-benzoyl-Arg + 4-nitroaniline
-
-
-
-
?
N-benzoyl-Arg-4-nitroanilide + H2O
N-benzoyl-Arg + 4-nitroaniline
-
-
-
?
N-benzoyl-Arg-4-nitroanilide + H2O
N-benzoyl-Arg + 4-nitroaniline
-
-
-
-
?
additional information
?
-
-
the abnormal catalytic site environment of chymopapain A may have consequences for the acylation step of the catalytic act, does not pertub the conformation of the bound acyl group at the acyl-enzyme-intermediate stage of catalysis
-
-
?
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
-
-
?
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2,4-dichlorocyclohexan-1-one + cyclohexanone
?
yield: 43%, 80:20 anti/syn, ee (anti): 81%
-
-
?
2,6-dichlorocyclohexan-1-one + cyclohexanone
?
yield: 39%, 99:01 anti/syn, ee (anti): 58%
-
-
?
2-chlorocyclohexan-1-one + cyclohexanone
?
yield: 30%, 86:14 anti/syn, ee (anti): 79%
-
-
?
2-nitrocyclohexan-1-one + cyclohexanone
?
yield: 24%, 87:13 anti/syn, ee (anti): 82%
-
-
?
3-chlorocyclohexan-1-one + cyclohexanone
?
yield: 32%, 65:35 anti/syn, ee (anti): 93%
-
-
?
3-nitrocyclohexan-1-one + cyclohexanone
?
yield: 41%, 87:13 anti/syn, ee (anti): 86%
-
-
?
4-bromocyclohexan-1-one + cyclohexanone
?
yield: 29%, 81:19 anti/syn, ee (anti): 84%
-
-
?
4-chlorocyclohexan-1-one + cyclohexanone
?
yield: 47%, 69:31 anti/syn, ee (anti): 75%
-
-
?
4-cyanobenzaldehyde + cyclohexanone
4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile
4-cyanocyclohexan-1-one + cyclohexanone
?
yield: 60%, 72:28 anti/syn, ee (anti): 76%
-
-
?
4-methylcyclohexan-1-one + cyclohexanone
?
yield: 23%, 63:37 anti/syn, ee (anti): 96%
-
-
?
4-nitrocyclohexan-1-one + acetaldehyde
?
yield: 12%, ee (anti): 14%
-
-
?
4-nitrocyclohexan-1-one + cycloheptanone
?
yield: 19%, 47:53 anti/syn, ee (anti): 26%
-
-
?
4-nitrocyclohexan-1-one + cyclohexanone
?
yield: 69%, 63:37 anti/syn, ee (anti): 78%
-
-
?
4-nitrocyclohexan-1-one + cyclopentanone
?
yield: 73%, 56:44 anti/syn, ee (anti): 52%
-
-
?
furan-2-carbaldehyde + cyclohexanone
?
yield: 16%, 63:37 anti/syn, ee (anti): 61%
-
-
?
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
-
-
?
4-cyanobenzaldehyde + cyclohexanone
4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile
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-cyanobenzaldehyde + cyclohexanone
4-[hydroxy(2-oxocyclohexyl)methyl]benzonitrile
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
-
-
?
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Brocklehurst, K.; Baines, B.S.; Salih, E.; Hatzoulis, C.
Chymopapain S is chymopapain A
Biochem. J.
221
553-554
1984
Carica papaya
brenda
Zucker, S.; Buttle, D.J.; Nicklin, M.J.H.; Barrett, A.J.
The proteolytic activities of chymopapain, papain, and papaya proteinase III
Biochim. Biophys. Acta
828
196-204
1985
Carica papaya
brenda
Robinson, G.W.
Isolation and characterization of papaya peptidase A from commercial chymopapain
Biochemistry
14
3695-3700
1975
Carica papaya
brenda
Baines, B.S.; Brocklehurst, K.; Carey, P.R.; Jarvis, M.; Salih, E.; Storer, A.C.
Chymopapain A. Purification and investigation by covalent chromatography and characterization by two-protonic-state reactivity-probe kinetics, steady-state kinetics and resonance Raman spectroscopy of some dithioacyl derivatives
Biochem. J.
233
119-129
1986
Carica papaya
brenda
Solis-Mendiola, S.; Zubillaga-Luna, R.; Rojo-Dominguez, A.; Hernandez-Arana, A.
Structural similarity of chymopapain forms as indicated by circular dichroism
Biochem. J.
257
183-186
1989
Carica papaya
brenda
Dubois, T.; Jacquet, A.; Schnek, A.G.; Looze, Y.
The thiol proteinases from the latex of Carica papaya L. I. Fractionation, purification and preliminary characterization
Biol. Chem. Hoppe-Seyler
369
733-740
1988
Carica papaya
brenda
Solis-Mendiola, S.; Gutierrez-Gonzales, L.H.; Arroyo-Reyna, A.; Padilla-Zuniga, J.; Rojo-Dominguez, A.; Hernandez-Arana, A.
pH Dependence of the activation parameters for chymopapain unfolding: influence of ion pairs on the kinetic stability of proteins
Biochim. Biophys. Acta
1388
363-372
1998
Carica papaya
brenda
Azarkan, M.; Maes, D.; Bouckaert, J.; Dao Thi, M.H.; Wyns, L.; Looze, Y.
Thiol pegylation facilitates purification of chymopapain leading to diffraction studies at 1.4 A resolution
J. Chromatogr. A
749
69-72
1996
Carica papaya
-
brenda
Buttle, D.J.; Barrett, A.J.
Chymopapain. Chromatographic purification and immunological characterization
Biochem. J.
223
81-88
1984
Carica papaya
brenda
Rodis, P.; Hoff, J.E.
Naturally occurring protein crystals in the potato. Inhibitor of papain, chymopapain, and ficin
Plant Physiol.
74
907-911
1984
Carica papaya
brenda
Khan, I.U.; Polgar, L.
Purification and characterization of a novel proteinase, chymopapain S
Biochim. Biophys. Acta
760
350-356
1983
Carica papaya
-
brenda
Lynn, K.R.
An isolation of chymopapain
J. Chromatogr.
84
423-425
1973
Carica papaya
brenda
Kunimitsu, D.K.; Yasunobu, K.T.
Chymopapain B
Methods Enzymol.
19
244-252
1970
Carica papaya
-
brenda
Kunimitsu, D.K.; Yasunobu, K.T.
Chymopapain. IV. The chromatographic fractionation of partially purified chymopapain and the characterization of crystalline chymopapain B
Biochim. Biophys. Acta
139
405-417
1967
Carica papaya
brenda
Ebata, M.; Yasunobu, K.T.
Chymopapain. I. Isolation, crystallization, and preliminary characterization
J. Biol. Chem.
237
1086-1094
1962
Carica papaya
brenda
Vincentelli, J.; Bouckaert, J.; Jacquet, A.; Paul, C.; Thi, M.H.S.; Poortmans, F.; Wyns, L.; Looze, Y.
Purification of chymopapain as a single fully active cysteine-proteinase led to reexamination of its catalytic properties and to crystallization
Int. J. Bio-Chromatogr.
1
209-226
1995
Carica papaya
-
brenda
Maes, D.; Bouckaert, J.; Poortmans, F.; Wyns, L.; Looze, Y.
Structure of chymopapain at 1.7 A resolution
Biochemistry
35
16292-16298
1996
Carica papaya
brenda
Walreavens, V.; Jaziri, M.; van Bleeumen, J.; Schnek, A.G.; Kleinschmidt, T.; Looze, Y.
Isolation and preliminary characterization of the cysteine-proteinases from the latex of Carica candamarcensis Hook
Biol. Chem. Hoppe-Seyler
374
501-506
1993
Vasconcellea cundinamarcensis, Carica papaya, Vasconcellea cundinamarcensis Hook
brenda
Jaquet, A.; Kleinschmidt, T.; Schnek, A.G.; Looze, Y.; Braunitzer, G.
The thiol proteinases from the latex of Carica papaya L. III. The primary structure of chymopapain
Biol. Chem. Hoppe-Seyler
370
425-434
1989
Carica papaya
brenda
Buttle, D.J.; Dando, P.M.; Coe, P.F.; Sharp, S.L.; Shepherd, S.T.; Barrett, A.J.
The preparation of fully active chymopapain free of contaminating proteinases
Biol. Chem. Hoppe-Seyler
371
1083-1088
1990
Carica papaya
brenda
Bjrk, I.; Ylinenjrvi, K.
Interaction between chicken cystatin and the cysteine proteinases actinidin, chymopapain A, and ficin
Biochemistry
29
1770-1776
1990
Carica papaya
brenda
Azarkan, M.; El Moussaoui, A.; van Wuytswinkel, D.; Dehon, G.; Looze, Y.
Fractionation and purification of the enzymes stored in the latex of Carica papaya
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790
229-238
2003
Carica papaya
brenda
Huet, J.; Looze, Y.; Bartik, K.; Raussens, V.; Wintjens, R.; Boussard, P.
Structural characterization of the papaya cysteine proteinases at low pH
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341
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2006
Carica papaya
brenda
Azarkan, M.; Dibiani, R.; Baulard, C.; Baeyens-Volant, D.
Effects of mechanical wounding on Carica papaya cysteine endopeptidases accumulation and activity
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38
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2006
Carica papaya
brenda
Lopez-Arenas, L.; Solis-Mendiola, S.; Padilla-Zuniga, J.; Hernandez-Arana, A.
Hofmeister effects in protein unfolding kinetics: estimation of changes in surface area upon formation of the transition state
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1764
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2006
Carica papaya
brenda
Theodorou, L.G.; Bieth, J.G.; Papamichael, E.M.
The catalytic mode of cysteine proteinases of papain (C1) family
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98
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2007
Carica papaya
brenda
Dang, L.; Wardlaw, D.; Hukins, D.W.
Removal of nucleus pulposus from the intervertebral disc - the use of chymopapain enhances mechanical removal with rongeurs: a laboratory study
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8
122
2007
Carica papaya
brenda
Fatima, S.; Khan, R.H.
Effect of polyethylene glycols on the function and structure of thiol proteases
J. Biochem.
142
65-72
2007
Carica papaya
brenda
Cornell, H.J.; Doherty, W.; Stelmasiak, T.
Papaya latex enzymes capable of detoxification of gliadin
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38
155-165
2009
Carica papaya, Carica papaya (P14080)
brenda
Diaz-Mochon, J.J.; Planonth, S.; Bradley, M.
From 10,000 to 1: Selective synthesis and enzymatic evaluation of fluorescence resonance energy transfer peptides as specific substrates for chymopapain
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384
101-105
2009
Carica papaya
brenda
Chen, W.H.; Liu, H.Y.; Lo, W.C.; Wu, S.C.; Chi, C.H.; Chang, H.Y.; Hsiao, S.H.; Wu, C.H.; Chiu, W.T.; Chen, B.J.; Deng, W.P.
Intervertebral disc regeneration in an ex vivo culture system using mesenchymal stem cells and platelet-rich plasma
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30
5523-5533
2009
Carica papaya
brenda
Guo, J.; Yang, L.; Liu, X.; Zhang, H.; Qian, B.; Zhang, D.
Applicability of the chymopapain gene used as endogenous reference gene for transgenic huanong no. 1 papaya detection
J. Agric. Food Chem.
57
6502-6509
2009
Carica papaya (Q5Q047), Carica papaya
brenda
He, Y.; Li, H.; Chen, Y.; Xue, Y.; Yuan, Y.; Guan, Z.
Chymopapain-catalyzed direct asymmetric aldol reaction
Adv. Synth. Catal.
354
712-719
2012
Carica papaya (P14080)
-
brenda
Kim, C.J.; Lee, D.I.; Lee, C.H.; Ahn, I.S.
A dityrosine-based substrate for a protease assay: application for the selective assessment of papain and chymopapain activity
Anal. Chim. Acta
723
101-107
2012
Carica papaya (P14080)
brenda
Rodrigues, S.P.; Ventura, J.A.; Aguilar, C.; Nakayasu, E.S.; Choi, H.; Sobreira, T.J.; Nohara, L.L.; Wermelinger, L.S.; Almeida, I.C.; Zingali, R.B.; Fernandes, P.M.
Label-free quantitative proteomics reveals differentially regulated proteins in the latex of sticky diseased Carica papaya L. plants
J. Proteomics
75
3191-3198
2012
Carica papaya (P14080), Carica papaya (Q9SMH9), Carica papaya (Q9SMI0), Carica papaya (Q9SMI2)
brenda
Liu, J.; Sharma, A.; Niewiara, M.; Singh, R.; Ming, R.; Yu, Q.
Papain-like cysteine proteases in Carica papaya lineage-specific gene duplication and expansion
BMC Genomics
19
26
2018
Carica papaya (P14080), Carica papaya
brenda