US4800162A
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Method for resolution of steroisomers in multiphase and extractive membrane reactors
Assignee: Sumitomo Pharma America Inc
•
Filing: 1987-04-01
•
Granted: 1989-01-24
•
Expires: 2007-04-01
Abstract
Abstract This invention relates to the resolution of racemic mixtures of optically active compounds, including but not limited to the stereochemical purification of chiral organic esters, amides, carboxylic acids, alcohols, and amines. Novel methods utilizing multiphase and extractive enzyme membrane bioreactors are disclosed that selectively produce pure or substantially purified optically active compounds from achiral precursors or mixtures of isomers in which one or several of those isomers are biologically inactive or otherwise lack desirable characteristics. There are immiscible solvents on either side of the membrane.
Inventors
- 👤 Stephen L. Matson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 05:31
CPC Classifications
C; C12; C12N; C12N11/00; C12N11/02; B; B01; B01J; B01J19/00; B01J19/24; B01J19/2475; C07; C07C; C07C219/00; C07C219/02; C07C219/04; C07C219/10; C07C305/00; C07C305/02; C07C305/04; C07C305/10; C07C309/00; C07C309/63; C07C309/64; C07C309/65; C07C309/66; C07C327/00; C07C327/20; C07C327/32; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/091; C12M; C12M21/00; C12M21/18; C12M25/00; C12M25/02; C12M29/00; C12M29/04; C12M29/16; C12N11/08; C12N11/082; C12N11/087; C12P; C12P1/00; C12P41/00; C12P41/003; C12P41/005; C12P7/00; C12P7/40; B01J2219/00; B01J2219/00049; B01J2219/00051; B01J2219/00159; B01J2219/00162; B01J2219/00177
Claims Analysis
Total Claims: 160
Claim 1
Independent Claim
120 words
A method for resolving a racemic mixture comprising: a. providing in a first fluid a racemic mixture having at least a first and second stereoisomer to one side of an enzyme activated membrane wherein said enzyme which activates said membrane catalyzes the reaction of the first stereoisomer into a chiral product having an altered chemical composition; b. providing concurrently a second fluid, substantially immiscible in said first fluid, to the opposite side of said enzyme activated membrane, whereby said racemic mixture is resolved with said chiral product of step a principally diffusing into said second fluid from said enzyme activated membrane so that said second fluid predominantly includes said chiral product and said first fluid predominantly includes said second stereoisomer.
Claim 2
Independent Claim
120 words
A method for resolving a racemic mixture comprising: a. providing in a first fluid a racemic mixture having at least a first and second stereoisomer to one side of an enzyme activated membrane wherein said enzyme which activates said membrane catalyzes the reaction of the first stereoisomer into a chiral product having an altered chemical composition; b. providing concurrently a second fluid, substantially immiscible in said first fluid, to the opposite side of said enzyme activated membrane, whereby said racemic mixture is resolved with said chiral product of step a principally diffusing into said second fluid from said enzyme activated membrane so that said second fluid predominantly includes said chiral product and said first fluid predominantly includes said second stereoisomer.
Claim 3
Dependent Claim
13 words
The method of claim 1 wherein the first fluid is an organic-based solution.
Claim 4
Dependent Claim
13 words
The method of claim 1 wherein the second fluid is an aqueous solution.
Claim 5
Dependent Claim
13 words
The method of claim 1 wherein the first fluid is an aqueous solution.
Claim 6
Dependent Claim
13 words
The method of claim 1 wherein the second fluid is an organic-based solution.
Claim 7
Dependent Claim
34 words
The method of claim 1 wherein the reaction of step a is the selected from the group consisting of ester hydrolysis, ester formation, transesterification, transamination, amide hydrolysis, amide formation, hydantoin hydrolysis and nitrile hydrolysis.
Claim 8
Dependent Claim
17 words
The method of claim 1 wherein the racemic mixture comprises at least two isomers of an ester.
Claim 9
Dependent Claim
26 words
The method of claim 7 wherein the racemic mixture comprises at least two isomers of an ester prepared by reacting an alcohol with a racemic acid.
Claim 10
Dependent Claim
26 words
The method of claim 7 wherein the racemic mixture comprises at least two isomers of an ester prepared by reacting an acid with a racemic alcohol.
Claim 11
Dependent Claim
17 words
The method of claim 1 wherein the racemic mixture comprises at least two isomers of an amide.
Claim 12
Dependent Claim
26 words
The method of claim 10 wherein the racemic mixture comprises at least two isomers of an amide prepared by reacting an amine with a racemic acid.
Claim 13
Dependent Claim
26 words
The method of claim 10 wherein the racemic mixture comprises at least two isomers of an amide prepared by reacting an acid with a racemic amine.
Claim 14
Dependent Claim
18 words
The method of claim 1 wherein the racemic mixture comprises at least two isomers of a carboxylic acid.
Claim 15
Dependent Claim
17 words
The method of claim 1 wherein the racemic mixture comprises at least two isomers of an alcohol.
Claim 16
Dependent Claim
17 words
The method of claim 1 wherein the racemic mixture comprises at least two isomers of an amine.
Claim 17
Dependent Claim
17 words
The method of claim 1 wherein the racemic mixture comprises at least two isomers of a hydantoin.
Claim 18
Dependent Claim
18 words
The method of claim 1 wherein the racemic mixture comprises at least two isomers of a nitrile compound.
Claim 19
Dependent Claim
31 words
The method of claim 1 wherein the racemic mixture comprises a compound selected from the group consisting of beta blockers, pheromones, prostaglandins, steroids, flavoring agents, fragrance agents, pharmaceuticals, pesticides, and herbicides.
Claim 20
Dependent Claim
12 words
The method of claim 1 wherein the membrane is a hydrophilic membrane.
Claim 21
Dependent Claim
12 words
The method of claim 1 wherein the membrane is a microporous membrane.
Claim 22
Dependent Claim
16 words
The method of claim 1 wherein the enzyme which activates said membrane is a hydrolytic enzyme.
Claim 23
Dependent Claim
42 words
The method of claim 21 wherein the enzyme which activates said membrane is selected from the group consisting of lipases, carboxyl esterases, cholesterol esterase, acetylcholinesterase, peptidases, proteases, trypsin, chymotrypsin, subtilisin, rennin, pepsin, papain, carboxypeptidases, aminopeptidases, amidases, acylases, penicillin acylase, nitrilases, and hydantoinases.
Claim 24
Dependent Claim
20 words
The method of claim 1 wherein the enzyme which activates said membrane is bound to a surface of said membrane.
Claim 25
Dependent Claim
20 words
The method of claim 1 wherein the enzyme which activates said membrane is bound to both surfaces of said membrane.
Claim 26
Dependent Claim
17 words
The method of claim 1 wherein the enzyme which activates said membrane is located within said membrane.
Claim 27
Dependent Claim
20 words
The method of claim 1 wherein the enzyme is contained within the pore spaces of an asymmetric and microporous membrane.
Claim 28
Dependent Claim
21 words
The method of claim 1 wherein the enzyme is adsorbed on said membrane on the pore wall surfaces of said membrane.
Claim 29
Dependent Claim
19 words
The method of claim 1 wherein the enzyme is entrapped within a polymeric gel within pores of said membrane.
Claim 30
Dependent Claim
19 words
The method of claim 1 wherein the enzyme is covalently coupled to the pore wall surfaces of said membrane.
Claim 31
Dependent Claim
16 words
The method of claim 1 wherein the enzyme is crosslinked within pore spaces of said membrane.
Claim 32
Dependent Claim
18 words
The method of claim 1 wherein said enzyme is crosslinked on the pore wall surfaces of said membrane.
Claim 33
Dependent Claim
31 words
The method of claim 1 wherein the enzyme is provided in a form selected from the group consisting of purified enzyme, cell extract, cell lysate, partially purified enzyme and whole cells.
Claim 34
Dependent Claim
25 words
The method of claim 1 wherein the enzyme is selected from the group consisting of a nitrile hydratase, a transaminase, a oxynitrilase, and a lyase.
Claim 35
Dependent Claim
13 words
The method of claim 1 wherein said enzyme is derived from a microorganism.
Claim 36
Dependent Claim
13 words
The method of claim 1 wherein the enzyme is derived from a mammal.
Claim 37
Dependent Claim
23 words
The method of claim 1 wherein the membrane form is one selected from the group consisting of flat sheet, hollow fiber, and tube.
Claim 38
Dependent Claim
13 words
The method of claim 36 wherein the membrane is a skinned, microporous membrane.
Claim 39
Dependent Claim
51 words
The method of claim 1 wherein the membrane is constructed of material selected from the group consisting of regenerated cellulose, the esters of cellulose, polyacrylonitrile, polyacrylonitrile copolymers, polyurethane-containing copolymers, polyarylsulfones, polyarylethersulfones, polyarylsulfone blends, polyaryethersulfone blends, polyvinylidene fluoride, polytetrafluoroethylene, polyvinylalcohol, aliphatic polyamides, aromatic polyamides, polyimides, polyetherimides, polyesters, polycarbonates, polyolefins, polybenzimidazole, and polybenzimidazolone.
Claim 40
Dependent Claim
28 words
The method of claim 1 wherein the membrane is hydrophobic, one of said first or second fluids is an aqueous solution, and the aqueous solution is under pressure.
Claim 41
Dependent Claim
28 words
The method of claim 1 wherein the membrane is hydrophilic, one of said first or second fluids is an organic-based solution, and said organic-based solution is under pressure.
Claim 42
Dependent Claim
24 words
The method of claim 3 and 4 wherein the pH of said first fluid ranges from a pH of 2 to about pH 10.
Claim 43
Dependent Claim
13 words
The method of claim 41 wherein the pH is between 5.0 and 8.5.
Claim 44
Dependent Claim
20 words
The method of claim 1 wherein the reaction takes place at a temperature from about 15° C. to 70° C.
Claim 45
Dependent Claim
19 words
The method of claim 43 wherein the said reaction takes place at about 20° C. to about 45° C.
Claim 46
Dependent Claim
22 words
The method of claim 1 wherein the chiral product is substantially more soluble in said second fluid than in said first fluid.
Claim 47
Dependent Claim
24 words
The method of claim 1 wherein said first and second stereoisomers are substantially more soluble in said first fluid than in said second fluid.
Claim 48
Dependent Claim
20 words
The method of claim 1 wherein the first fluid moves in a direction that is countercurrent to said second fluid.
Claim 49
Dependent Claim
25 words
The method of claim 1 wherein the racemic mixture comprises at least two stereoisomers of an ester and said chiral product is a carboxylic acid.
Claim 50
Dependent Claim
25 words
The method of claim 1 wherein the racemic mixture comprises at least two stereoisomers of an amide and said chiral product is a carboxylic acid.
Claim 51
Dependent Claim
24 words
The method of claim 1 wherein said racemic mixture comprises at least two stereoisomers of an ester and said chiral product is an alcohol.
Claim 52
Dependent Claim
24 words
The method of claim 1 wherein said racemic mixture comprises at least two steroisomers of an amide and said chiral product is an amine.
Claim 53
Dependent Claim
15 words
The method of claim 1 further comprising separating said chiral product from said second fluid.
Claim 54
Dependent Claim
15 words
The method of claim 1 further comprising separating said second stereoisomer from said first fluid.
Claim 55
Dependent Claim
16 words
The method of claim 1 wherein said first fluid is substantially depleted of said first stereoisomer.
Claim 56
Dependent Claim
15 words
The method of claim 1 wherein the racemic mixture is continually recycled to the membrane.
Claim 57
Dependent Claim
36 words
The method of claim 1 further comprising removing said first fluid containing the second stereoisomer from said enzyme-activated membrane, racemizing said second stereoisomer, and reintroducing said racemized stereoisomers in the first fluid to said enzyme-activated membrane.
Claim 58
Dependent Claim
51 words
The method of claim 1 further comprising removing said second fluid containing said chiral product from the enzyme-activated membrane, racemizing said chiral product, chemically converting said racemized product to the chemical form of said first and second stereoisomers, and reintroducing said racemized stereoisomers in said first fluid to said enzyme-activated membrane.
Claim 59
Dependent Claim
32 words
The method of claim 1 wherein the volumetric flowrates of said first fluid and said second fluid flowing past said enzyme-activated membrane differ by a factor from about two to about ten.
Claim 60
Independent Claim
129 words
A method for resolving a racemic mixture comprising: a. providing a racemic mixture having at least a first and second stereoisomer in a first fluid to one side of an enzyme activated membrane wherein said enzyme which activates said membrane catalyzes the reaction of the first stereoisomer into a chiral product having an altered chemical composition and a second product and; b. providing concurrently a second fluid, substantially immiscible in said first fluid, to the opposite side of said enzyme activated membrane said chiral product of step a principally diffusing into said first fluid from said enzyme activated membrane and said second product principally diffusing into said second fluid, whereby said racemic mixture is resolved with said first fluid containing said second stereoisomer and said chemically distinct chiral product.
Claim 61
Independent Claim
129 words
A method for resolving a racemic mixture comprising: a. providing a racemic mixture having at least a first and second stereoisomer in a first fluid to one side of an enzyme activated membrane wherein said enzyme which activates said membrane catalyzes the reaction of the first stereoisomer into a chiral product having an altered chemical composition and a second product and; b. providing concurrently a second fluid, substantially immiscible in said first fluid, to the opposite side of said enzyme activated membrane said chiral product of step a principally diffusing into said first fluid from said enzyme activated membrane and said second product principally diffusing into said second fluid, whereby said racemic mixture is resolved with said first fluid containing said second stereoisomer and said chemically distinct chiral product.
Claim 62
Dependent Claim
13 words
The method of claim 59 wherein the first fluid is an organic-based solution.
Claim 63
Dependent Claim
13 words
The method of claim 59 wherein the second fluid is an aqueous solution.
Claim 64
Dependent Claim
13 words
The method of claim 59 wherein the first fluid is an aqueous solution.
Claim 65
Dependent Claim
13 words
The method of claim 59 wherein the second fluid is an organic-based solution.
Claim 66
Dependent Claim
34 words
The method of claim 59 wherein the reaction of step a is the selected from the group consisting of ester hydrolysis, ester formation, transesterification, transamination, amide hydrolysis, amide formation, hydantoin hydrolysis and nitrile hydrolysis.
Claim 67
Dependent Claim
17 words
The method of claim 59 wherein the racemic mixture comprises at least two isomers of an ester.
Claim 68
Dependent Claim
26 words
The method of claim 65 wherein the racemic mixture comprises at least two isomers of an ester prepared by reacting an alcohol with a racemic acid.
Claim 69
Dependent Claim
26 words
The method of claim 65 wherein the racemic mixture comprises at least two isomers of an ester prepared by reacting an acid with a racemic alcohol.
Claim 70
Dependent Claim
17 words
The method of claim 59 wherein the racemic mixture comprises at least two isomers of an amide.
Claim 71
Dependent Claim
26 words
The method of claim 68 wherein the racemic mixture comprises at least two isomers of an amide prepared by reacting an amine with a racemic acid.
Claim 72
Dependent Claim
26 words
The method of claim 68 wherein the racemic mixture comprises at least two isomers of an amide prepared by reacting an acid with a racemic amine.
Claim 73
Dependent Claim
18 words
The method of claim 59 wherein the racemic mixture comprises at least two isomers of a carboxylic acid.
Claim 74
Dependent Claim
17 words
The method of claim 59 wherein the racemic mixture comprises at least two isomers of an alcohol.
Claim 75
Dependent Claim
17 words
The method of claim 59 wherein the racemic mixture comprises at least two isomers of an amine.
Claim 76
Dependent Claim
17 words
The method of claim 59 wherein the racemic mixture comprises at least two isomers of a hydantoin.
Claim 77
Dependent Claim
18 words
The method of claim 59 wherein the racemic mixture comprises at least two isomer of a nitrile compound.
Claim 78
Dependent Claim
31 words
The method of claim 59 wherein the racemic mixture comprises a compound selected from the group consisting of beta blockers, pheromones, prostaglandins, steroids, flavoring agents, fragrance agents, pharmaceuticals, pesticides, and herbicides.
Claim 79
Dependent Claim
12 words
The method of claim 59 wherein the membrane is a hydrophilic membrane.
Claim 80
Dependent Claim
12 words
The method of claim 59 wherein the membrane is a microporous membrane.
Claim 81
Dependent Claim
16 words
The method of claim 59 wherein the enzyme which activates said membrane is a hydrolytic enzyme.
Claim 82
Dependent Claim
42 words
The method of claim 79 wherein the enzyme which activates said membrane is selected from the group consisting of lipases, carboxyl esterases, cholesterol esterase, acetylcholinesterase, peptidases, proteases, trypsin, chymotrypsin, subtilisin, rennin, pepsin, papain, carboxypeptidases, aminopeptidases, amidases, acylases, penicillin acylase, nitrilases, and hydantoinases.
Claim 83
Dependent Claim
20 words
The method of claim 59 wherein the enzyme which activates said membrane is bound to a surface of said membrane.
Claim 84
Dependent Claim
20 words
The method of claim 59 wherein the enzyme which activates said membrane is bound to both surfaces of said membrane.
Claim 85
Dependent Claim
17 words
The method of claim 59 wherein the enzyme which activates said membrane is located within said membrane.
Claim 86
Dependent Claim
20 words
The method of claim 59 wherein the enzyme is contained within the pore spaces of an asymmetric and microporous membrane.
Claim 87
Dependent Claim
21 words
The method of claim 59 wherein the enzyme is adsorbed on said membrane on the pore wall surfaces of said membrane.
Claim 88
Dependent Claim
19 words
The method of claim 59 wherein the enzyme is entrapped within a polymeric gel within pores of said membrane.
Claim 89
Dependent Claim
19 words
The method of claim 59 wherein the enzyme is covalently coupled to the pore wall surfaces of said membrane.
Claim 90
Dependent Claim
16 words
The method of claim 59 wherein the enzyme is crosslinked within pore spaces of said membrane.
Claim 91
Dependent Claim
18 words
The method of claim 59 wherein said enzyme is crosslinked on the pore wall surfaces of said membrane.
Claim 92
Dependent Claim
31 words
The method of claim 59 wherein the enzyme is provided in a form selected from the group consisting of purified enzyme, cell extract, cell lysate, partially purified enzyme and whole cells.
Claim 93
Dependent Claim
25 words
The method of claim 59 wherein the enzyme is selected from the group consisting of a nitrile hydratase, a transaminase, an oxynitrilase and a lyase.
Claim 94
Dependent Claim
13 words
The method of claim 59 wherein said enzyme is derived from a microorganism.
Claim 95
Dependent Claim
13 words
The method of claim 59 wherein the enzyme is derived from a mammal.
Claim 96
Dependent Claim
23 words
The method of claim 59 wherein the membrane form is one selected from the group consisting of flat sheet, hollow fiber, and tube.
Claim 97
Dependent Claim
14 words
The method of claim 94 wherein the membrane is in a skinned, microporous membrane.
Claim 98
Dependent Claim
51 words
The method of claim 59 wherein the membrane is constructed of material selected from the group consisting of regenerated cellulose, the esters of cellulose, polyacrylonitrile, polyacrylonitrile copolymers, polyurethane-containing copolymers, polyarylsulfones, polyarylethersulfones, polyarylsulfone blends, polyaryethersulfone blends, polyvinylidene fluoride, polytetrafluoroethylene, polyvinylalcohol, aliphatic polyamide, aromatic polyamides, polyimides, polyesters, polycarbonates, polyetherimides, polyolefins, polybenzimidazole, and polybenzimidazolone.
Claim 99
Dependent Claim
20 words
The method of claim 59 wherein the membrane is hydrophobic and the first fluid is an aqueous solution under pressure.
Claim 100
Dependent Claim
20 words
The method of claim 59 wherein the membrane is hydrophobic and the second fluid is an aqueous solution under pressure.
Claim 101
Dependent Claim
28 words
The method of claim 59 wherein the membrane is hydrophilic, one of said first or second fluids is an organic-based solution, and said organic-based solution is under pressure.
Claim 102
Dependent Claim
25 words
The method of claim 61 and 62 wherein the pH of said first fluid ranges from a pH of about 2 to about pH 10.
Claim 103
Dependent Claim
15 words
The method of claim 100 wherein the pH is between about 5.0 and about 8.5.
Claim 104
Dependent Claim
20 words
The method of claim 59 wherein the reaction takes place at a temperature from about 15° C. to 70° C.
Claim 105
Dependent Claim
19 words
The method of claim 102 wherein the said reaction takes place at about 20° C. to about 45° C.
Claim 106
Dependent Claim
22 words
The method of claim 59 wherein the chiral product is substantially more soluble in said first fluid than in said second fluid.
Claim 107
Dependent Claim
24 words
The method of claim 59 wherein said first and second stereoisomers are substantially more soluble in said first fluid than in said second fluid.
Claim 108
Dependent Claim
20 words
The method of claim 59 wherein the first fluid moves in a direction that is countercurrent to said second fluid.
Claim 109
Dependent Claim
25 words
The method of claim 59 wherein the racemic mixture comprises at least two stereoisomers of an ester and said chiral product is a carboxylic acid.
Claim 110
Dependent Claim
25 words
The method of claim 59 wherein the racemic mixture comprises at least two stereoisomers of an amide and said chiral product is a carboxylic acid.
Claim 111
Dependent Claim
24 words
The method of claim 59 wherein said racemic mixture comprises at least two stereoisomers of an ester and said chiral product is an alcohol.
Claim 112
Dependent Claim
24 words
The method of claim 59 wherein said racemic mixture comprises at least two stereoisomers of an amide and said chiral product is an amine.
Claim 113
Dependent Claim
15 words
The method of claim 59 further comprising separating said chiral product from said first fluid.
Claim 114
Dependent Claim
15 words
The method of claim 59 further comprising separating said second stereoisomer from said first fluid.
Claim 115
Dependent Claim
16 words
The method of claim 59 wherein said first fluid is substantially depleted of said first stereoisomer.
Claim 116
Dependent Claim
26 words
The method of claim 59 wherein the mixture of said second stereoisomer and said chiral product in said first fluid is continually recycled to the membrane.
Claim 117
Dependent Claim
48 words
The method of claim 59 further comprising removing said first fluid containing said second stereoisomer and said chiral product from said enzyme-activated membrane, recovering said chiral product from said first fluid, racemizing said second stereoisomer, and reintroducing said racemized stereoisomers in the first fluid to said enzyme-activated membrane.
Claim 118
Dependent Claim
32 words
The method of claim 59 wherein the volumetric flowrates past said enzyme-activated membrane of said first fluid and said second fluid differ by a factor of from about two to about ten.
Claim 119
Independent Claim
93 words
A method for producing a chiral product from an achiral precursor comprising: a. providing a first fluid containing an achiral precursor to one side of an enzyme activated membrane wherein said enzyme which activates said membrane catalyzes the reaction of said achiral precursor into a chiral product; b. providing concurrently a second fluid substantially immiscible in said first fluid, to the opposite side of said enzyme activated membrane said chiral product of step a, principally diffusing into said second fluid from said enzyme activated membrane, whereby said second fluid contains said chiral product.
Claim 120
Independent Claim
93 words
A method for producing a chiral product from an achiral precursor comprising: a. providing a first fluid containing an achiral precursor to one side of an enzyme activated membrane wherein said enzyme which activates said membrane catalyzes the reaction of said achiral precursor into a chiral product; b. providing concurrently a second fluid substantially immiscible in said first fluid, to the opposite side of said enzyme activated membrane said chiral product of step a, principally diffusing into said second fluid from said enzyme activated membrane, whereby said second fluid contains said chiral product.
Claim 121
Dependent Claim
13 words
The method of claim 117 wherein the first fluid is an organic-based solution.
Claim 122
Dependent Claim
13 words
The method of claim 117 wherein the second fluid is an aqueous solution.
Claim 123
Dependent Claim
13 words
The method of claim 117 wherein the first fluid is an aqueous solution.
Claim 124
Dependent Claim
13 words
The method of claim 117 wherein the second fluid is an organic-based solution.
Claim 125
Dependent Claim
34 words
The method of claim 117 wherein the chiral product is selected from the group consisting of organic acids, alcohols, esters, amides, amines, hydantoins, amino nitriles, pharmaceuticals, fragrance agents, flavoring agents, pheromones, pesticides and herbicides.
Claim 126
Dependent Claim
32 words
The method of claim 117 wherein the reaction of step a is the selected from the group consisting of ester hydrolysis, ester formation, transesterification, transamination, amide hydrolysis, amide formation, and nitrile hydrolysis.
Claim 127
Dependent Claim
16 words
The method of claim 117 wherein the enzyme which activates said membrane is a hydrolytic enzyme.
Claim 128
Dependent Claim
20 words
The method of claim 124 wherein the enzyme is selected from the group consisting of lipases, carboxyl esterases and amidases.
Claim 129
Dependent Claim
27 words
The method of claim 117 wherein the reaction of step a is one of asymmetric addition of a chemical moiety across a carbon-to-carbon or carbon-to-oxygen double bond.
Claim 130
Dependent Claim
15 words
The method of claim 126 wherein the enzyme which activates said membrane is a lyase.
Claim 131
Dependent Claim
14 words
The method of claim 126 wherein the lyase is oxynitrilase or an ammonia lyase.
Claim 132
Dependent Claim
12 words
The method of claim 117 wherein the membrane is a hydrophilic membrane.
Claim 133
Dependent Claim
12 words
The method of claim 117 wherein the membrane is a microporous membrane.
Claim 134
Dependent Claim
20 words
The method of claim 117 wherein the enzyme which activates said membrane is bound to a surface of said membrane.
Claim 135
Dependent Claim
20 words
The method of claim 117 wherein the enzyme which activates said membrane is bound to both surfaces of said membrane.
Claim 136
Dependent Claim
17 words
The method of claim 117 wherein the enzyme which activates said membrane is located within said membrane.
Claim 137
Dependent Claim
20 words
The method of claim 117 wherein the enzyme is contained within the pore spaces of an asymmetric and microporous membrane.
Claim 138
Dependent Claim
21 words
The method of claim 117 wherein the enzyme is adsorbed on said membrane on the pore wall surfaces of said membrane.
Claim 139
Dependent Claim
19 words
The method of claim 117 wherein the enzyme is entrapped within a polymeric gel within pores of said membrane.
Claim 140
Dependent Claim
19 words
The method of claim 117 wherein the enzyme is covalently coupled to the pore wall surfaces of said membrane.
Claim 141
Dependent Claim
16 words
The method of claim 117 wherein the enzyme is crosslinked within pore spaces of said membrane.
Claim 142
Dependent Claim
18 words
The method of claim 117 wherein said enzyme is crosslinked on the pore wall surfaces of said membrane.
Claim 143
Dependent Claim
31 words
The method of claim 117 wherein the enzyme is provided in a form selected from the group consisting of purified enzyme, cell extract, cell lysate, partially purified enzyme and whole cells.
Claim 144
Dependent Claim
13 words
The method of claim 117 wherein said enzyme is derived from a microorganism.
Claim 145
Dependent Claim
13 words
The method of claim 117 wherein the enzyme is derived from a mammal.
Claim 146
Dependent Claim
23 words
The method of claim 117 wherein the membrane form is one selected from the group consisting of flat sheet, hollow fiber and tube.
Claim 147
Dependent Claim
14 words
The method of claim 143 wherein the membrane is in a skinned, microporous membrane.
Claim 148
Dependent Claim
51 words
The method of claim 117 wherein the membrane is constructed of material selected from the group consisting of regenerated cellulose, the esters of cellulose, polyacrylonitrile, polyacrylonitrile copolymers, polyurethane-containing copolymers, polyarylsulfones, polyarylethersulfones, polyarylsulfone blends, polyaryethersulfone blends, polyvinylidene fluoride, polytetrafluoroethylene, polyvinylalcohol, aliphatic polyamides, aromatic polyamides, polyimides, polyetherimides, polyesters, polycarbonates, polyolefins, polybenzimidazole, and polybenzimidazolone.
Claim 149
Dependent Claim
28 words
The method of claim 117 wherein the membrane is hydrophobic, one of said first or second fluids is an aqueous solution, and the aqueous solution is under pressure.
Claim 150
Dependent Claim
28 words
The method of claim 117 wherein the membrane is hydrophilic, one of said first or second fluids is an organic-based solution, and said organic-based solution is under pressure.
Claim 151
Dependent Claim
28 words
The method of claim 117 wherein the membrane is hydrophilic, one of said first or second fluids is an organic-based solutions, and said organic-based solution is under pressure.
Claim 152
Dependent Claim
25 words
The method of claim 119 and 120 wherein the pH of said first fluid ranges from a pH of about 2 to about pH 10.
Claim 153
Dependent Claim
15 words
The method of claim 149 wherein the pH is between about 5.0 and about 8.5.
Claim 154
Dependent Claim
21 words
The method of claim 117 wherein the reaction takes place at a temperature from about 15° C. to about 70° C.
Claim 155
Dependent Claim
19 words
The method of claim 151 wherein the said reaction takes place at about 20° C. to about 45° C.
Claim 156
Dependent Claim
22 words
The method of claim 117 wherein the chiral product is substantially more soluble in said second fluid than in said first fluid.
Claim 157
Dependent Claim
22 words
The method of claim 117 wherein said achiral precursor is substantially more soluble in said first fluid than in said second fluid.
Claim 158
Dependent Claim
20 words
The method of claim 117 wherein the first fluid moves in a direction that is countercurrent to said second fluid.
Claim 159
Dependent Claim
15 words
The method of claim 117 further comprising separating said chiral product from said second fluid.
Claim 160
Dependent Claim
32 words
The method of claim 117 wherein the volumetric flowrates past said enzyme-activated membrane of said first fluid and said second fluid differ by a factor of from about two to about ten.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-01-24 | 1992-07-25 | 1993-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-01-24 | 1996-07-25 | 1997-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-01-24 | 2000-07-25 | 2001-01-24 | $7700.00 | Window Closed / Lapsed |