WO1998032336A2 - Enzyme-based bread improvers - Google Patents
Enzyme-based bread improvers Download PDFInfo
- Publication number
- WO1998032336A2 WO1998032336A2 PCT/GB1998/000080 GB9800080W WO9832336A2 WO 1998032336 A2 WO1998032336 A2 WO 1998032336A2 GB 9800080 W GB9800080 W GB 9800080W WO 9832336 A2 WO9832336 A2 WO 9832336A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- enzyme
- dough
- proving
- improver
- mixing
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D8/00—Methods for preparing or baking dough
- A21D8/02—Methods for preparing dough; Treating dough prior to baking
- A21D8/04—Methods for preparing dough; Treating dough prior to baking treating dough with microorganisms or enzymes
- A21D8/042—Methods for preparing dough; Treating dough prior to baking treating dough with microorganisms or enzymes with enzymes
Definitions
- the present invention relates to bread improvers, to enzyme preparations for use in bread improvers and to processes for preparing and using them.
- the invention relates to latent enzyme systems or preparations and their application in bread improver compositions and in the baking industry.
- Bread is made from four principal ingredients: flour, yeast, salt and water. It is usually prepared in three basic steps, and the end result is a baked loaf. The steps are: (1) the principal ingredients are mixed to form a dough and worked to develop a continuous visco- elastic gluten matrix; (2) the developed dough is then proved by incubation in warm, humid conditions to promote fermentation by the yeast causing the dough to rise; (3) the risen dough is then baked to gelatinize starch, denature protein and fix the dough structure.
- bread improvers may include oxidants (such as ascorbic acid), reducing agents (such as cysteine), fats, emulsifiers, anti-moulding agents, yeast foods and enzymes.
- a typical bread improver consists of enzymes (0.1-2.0%), ascorbic acid (0.3-2.0%), fat/emulsifier (10-30%), soya flour (0-99%), anti-mouiding agents (0-40%) and gypsum (0- 40%), and is added to between 0.25 and 5% by weight of flour in the dough.
- improver enzymes include degradative enzymes (especially carbohydrases such as amylases, hemiceilulases, pentosanases, pullulanases, xylanases and pectinases, but also lipases), redox enzymes
- oxygenases such as lipoxygenase
- Improver enzymes play a crucial r ⁇ le in determining the Theological, structural and ' compositional properties of the dough during mixing and proving, and have a dramatic impact on the quality of the bread produced.
- carbohydrases hydrolyse carbohydrates (such as polysaccharides) into smaller subunits (such as glucose and dextrins) which are used by the yeast as substrates for fermentation. They promote a soft, white crumb.
- the starch-degrading enzyme ⁇ -amylase (and in particular fungal ⁇ -amylase, referred to herein as "FAA") is used in large quantities in the baking industry, and breaks down starch into glucose and dextrins. It is extremely effective in improving loaf volume, crumb whiteness, softness of crumb, surface colour and keeping qualities Various pentosanases have similar effects, particularly in improving loaf volume and shape
- improver enzymes including ⁇ -amylase
- the improver enzymes need not be active within the dough at the mixing stage their beneficial effects are fully realised even when their activity is delayed until the proving stage or even later (e g during the early stages of baking)
- the inventors have therefore found that the problems associated with stickiness, low water holding capacity and softness at the mixing stage can be avoided if the improver enzymes are mixed in the dough in a latent state and activated during or after the proving stage
- the term "latent enzyme” is intended to define an enzyme which when present as part of a dough mix exhibits a differential activity profile over the course of mixing, proving and baking, its activity during mixing being low relative to its activity during or after proving
- the latent enzyme preparation may be active during or after proving but relatively inactive during mixing
- Latency may be achieved in a number of different ways
- the enzyme may be treated so that it is released into the dough in a controlled fashion, for example during the early stages of proving Controlled release may be achieved by encapsulation conveniently by coating a granular or microparticulate enzyme preparation with a sequestering agent (or capsule)
- the capsule may take any physical or chemical form so long as it serves to isolate the enzyme from its substrate(s) in the dough
- the capsule may be formed by coating with fat gelatin or starch (as described infra)
- the capsule may be formed by surface treating (e g by surface irradiation or roasting) particulate enzyme/carrier preparations to create a layer of denatured/inactivated enzyme which delays release of active enzyme into the dough
- the level of encapsulation required to effect the invention depends on the particular enzyme and in someapplications may be below 100% (and in some cases, e g when S-amylase is the enzyme, the level of encapsulation may be below 50%)
- Latency may also De achieved through the use of enzyme preparations in which the enzyme is in close physical association with an inhibitor (for example in admixture therewith in a binder), so that the enzyme is initially latent due to high local concentrations of the inhibitor but becomes progressively more active as the inhibitor diffuses away (or is broken down in the dough) during mixing
- an inhibitor for example in admixture therewith in a binder
- the temporal delay associated with the gradual dilution of the inhibitor effectively provides controlled release of enzyme activity
- a typical inhibitor for use in such embodiments is a pH modulator, such as an acidulant (e g ascorbic acid citric acid and/or sodium diacetate) or alkalifymg agent
- an acidulant e g ascorbic acid citric acid and/or sodium diacetate
- alkalifymg agent The choice of pH modulator (i e whether an acidulant or alkalifymg agent) will depend on the pH-activity curve of the improver enzyme to be made latent Such pH-activity curves can be established using routine biochemical assays known to those skilled in the art
- the pH modulator is an alkalifymg agent
- the pH modulators for use in the invention are sparingly soluble in the dough mix This facilitates control of their pH modifying effects in the dough and permits the establishment of pH inhomogeneities arising from a local effect of the pH modulating agent in a microe ⁇ vironment surrounding the improver enzyme(s) in the dough mix
- Suitable alkalifymg agents include food acceptable alkali salts, such as calcium hydroxide, calcium carbonate, magnesium hydroxide, sodium hydroxide and sodium bicarbonate
- the pH modulating agents discussed above are used as a secondary latency system designed to inhibit the activity of any enzyme leaching or escaping from an encapsulant acting as the primary latency system Such leaching or escape may occur du ⁇ ng mixing when the integrity of the encapsulant may be compromised by abrasion during mixing or storage
- the invention contemplates latent enzyme(s) in which latency is achieved by a primary system comprising an encapsulant (e g fat, gelatin or starch) and a secondary system comprising a pH modulating agent
- latency is achieved by initially providing the enzyme in a physically immobilized form, the enzyme being mobilized over the course of mixing
- latency is achieved by providing the enzyme to the dough during mixing in the form of an aggregate having a relatively small surface area volume ratio which gradually increases during mixing due to physical division, so increasing the availability of the enzyme over time
- the form of the enzyme must be selected such that the enzymes are not released immediately upon mixing, but rather is such that latency (and the activity profile discussed earlier) is achieved
- the term 'enzyme preparation is intended to cover any preparation of enzyme (howsoever obtained) at any level of purity, so long as the preparation is enzymically active
- the enzyme preparations of the invention include preparations exhibiting a plurality of different specific activities, and are conveniently in the form of more or less crude enzyme extracts in admixture with one or more carriers (such as gypsum or maltodext ⁇ n)
- the enzyme preparations for use according to the invention are preferably in microparticulate or granular form They are preferably "improver enzymes", which term is used herein to define those enzymes which, when present as part of a bread improver composition, are capable of contributing to its functional properties
- the invention also contemplates a latent enzyme preparation per se for use in the bread improver of the invention, as well as a functional flour per se comprising the bread improver or the latent enzyme preparation of the invention
- a dough or bread comprising the improver enzyme preparation or functional flour of the invention, as well as bakery concentrates and complete bakery mixes (e g bakery dry mixes) comprising various dough ingredients together with the enzyme preparation of the invention
- the present invention is broadly applicable, and the bread of the invention may be of any type, including, white, brown, wholemeal, wheatgerm, malted gram, softgrain soft rolls crusty rolls and buns (including tin, crusty and Danish varieties of any of the foregoing)
- the invention finds particular application in tin breads
- the invention also contemplates a process for preparing a dough comprising the step of (a) mixing the bread improver or latent enzyme of the invention with flour, yeast, salt and water, or (b) mixing the flour of the invention with yeast, salt and water
- the invention in another embodiment, relates to a process for preparing bread comprising the steps of (a) mixing a dough (for example the dough of the invention or a dough obtainable by, or produced by, the processes of the invention) in the presence of an improver enzyme, and (b) proving the mixed dough, wherein the action of the improver enzyme is substantially delayed until the proving step (b) (or later, e g during the early stages of baking prior to heat inactivation of the enzyme(s)).
- a dough for example the dough of the invention or a dough obtainable by, or produced by, the processes of the invention
- an improver enzyme for example the dough of the invention or a dough obtainable by, or produced by, the processes of the invention
- proving the mixed dough wherein the action of the improver enzyme is substantially delayed until the proving step (b) (or later, e g during the early stages of baking prior to heat inactivation of the enzyme(s)).
- the enzyme is preferably selected from any of amylase, for example ⁇ -amylase (e g fungal ⁇ -amylase), hemicellulase, pentosanase, xylanase, pectinase, pullulanase, other non-starch polysaccha ⁇ de degrading enzymes, redox enzymes (for example glucose oxidase, lipoxygenase or ascorbic acid oxidase), lipase, protease, ⁇ -mannanase, oxidoreductases (e g glucose-oxidase, sulfhydryl-oxidase, SS-isomerase, SS-transferase), carbohydrate- modifying enzymes or combinations of any of the foregoing
- ⁇ -amylase e g fungal ⁇ -amylase
- hemicellulase pentosanase
- xylanase x
- the enzyme(s) are of bacterial yeast mammalian or fungal origin They are also preferably heat resistant or thermostable for example being deactivated by the baking process but active during proving
- the enzyme for use in the invention is preferably (a) encapsulated (for example such that in use its release into the dough is substantially delayed until proving or post-proving), and/or (b) immobilized during mixing, and/or (c) repressed or inhibited during mixing; and/or (d) activated during or after proving, and/or (e) sequestered during mixing
- the encapsulant is preferably any of (a) fat, (b) gelatin, (c) gum (e g vegetable gum), (d) maltodext ⁇ n, (e) starch (e g modified starch), (f) emuisifiers, (g) waxes, (h) sugars
- Fats for use in the invention may comprise unmodified and/or hydrogenated and/or fractionated vegetable animal or marine oils (e g tallow lard, fish palm cottonseed or soybean oils)
- the fat preferably has a slip melting point of at least about 35°C and/or is provided and/or disposed in sufficient quantities relative to the enzyme that the enzyme is substantially sequestered from the dough during mixing and released during or after proving
- the slip melting point is selected to ensure that the fat is substantially solid during mixing at temperatures of from about 15°C to about 30°C and that significant melting (and hence release of enzyme) occurs at temperatures between about 30°C and 35°C (preferably above about 33°C)
- the release temperature (and hence the length of time available for released enzyme to act during proving) may vary within a wide range, providing that sufficient enzyme is released for sufficient time to exert a beneficial effect during or after proving
- a fat having a suitable release temperature based on the conditions selected for the proving process
- the enzyme will also be active for the early part of the baking stage, while the temperature is below that at which the enzyme becomes heat-denatured (about 50°C for fungal ⁇ -amylase)
- the enzyme may be encapsulated by any suitable process
- Many different such processes are known in the art, and include for example (a) spray drying, (b) solvent dehydration, (c) extrusion, (d) air suspension, (e) centrifugal extrusion, (f) coacervation, (g) spray chilling (e g as described in EP 0 393 963), (h) fluidized bed coating, (I) combinations of (a)-(h) Particularly preferred is the use of a fat encapsulant applied by spray chilling using methods and apparatus described in EP 0 393 963 (the teachings of which are incorporated herein by reference)
- the enzyme is released during or after proving by (a) temperature- mediated release (e g thermal breakdown of an encapsulant), (b) a water-mediated release, (b) an att ⁇ tional agent (e g an enzyme, surfactant or acidulant)
- a temperature- mediated release e g thermal breakdown of an encapsulant
- a water-mediated release e.g thermal breakdown of an encapsulant
- an att ⁇ tional agent e g an enzyme, surfactant or acidulant
- the term "attntional agent” is intended to define any agent (for example, a chemical moiety, an enzyme, or a particular physical condition or treatment) which breaks down a barrier between the enzyme and the dough to release the enzyme
- the attntional agent is an inherent property of the dough during or after proving, such as its temperature or moisture level
- the attritional agent is primarily the temperature differential between the mixing and post-mixing steps: the relatively high temperatures at the proving stage effectively melt the fat capsule and release the enzyme.
- the attritional agent may be (at least in part) the water present in the dough, which progressively degrades the starch capsule during mixing and proving to provide timed release of the enzyme (which can be optimized by varying the thickness of the starch capsule).
- the attritional agent may be a pectinase.
- Other suitable degradative enzymes may be used with other gums (such as guar, xanthan etc.).
- Timed release of the encapsulated enzyme may then be achieved by controlling the activity of the pectinase, for example by encapsulating it in a fat capsule designed to release the pectinase during or after proving.
- This system has the further benefit that the gum encapsulant increases the water binding capacity of the dough during mixing.
- the gum capsule is bifunctional, serving both to delay the release of the improver enzyme and to increase the water binding capacity of the dough.
- the invention also relates to a process for producing a latent enzyme which is active during or after dough proving but relatively inactive during dough mixing, the process comprising the step of encapsulating the enzyme.
- the encapsulant may be any of the aforementioned encapsulants and any of the aforementioned encapsulating techniques may be employed.
- the invention also contemplates a dough, bread or latent enzyme obtainable by (or produced by) the processes of the invention.
- the invention therefore permits inter alia higher levels of water to be added to the dough (without producing unacceptable stickiness/softness, so increasing yield.
- the invention also permits higher levels of improver to be added to the dough at any given level of moisture (so improving loaf volume, crumb colour, softness and keeping qualities and permitting the use of lower grade flours).
- Fat (Couva 700TM from Loders Croklaan) was melted and fungal ⁇ -amylase (hereinafter FAA) in a gypsum carrier was added in 50:50 ratio with the fat.
- Couva 700TM is a fractionated, hydrogenated, refined vegetable fat of non-lauric origin. It has a slip melting point of about 35°C and is hard at room temperature, 42% solid at 30°C and 8% solid at 35°C.
- the FAA used was Fungamyl BGTM from Novo Nordisk. This is a fungal amylase preparation from Aspergiilus oryzae.
- the enzyme hydrolyzes the ⁇ -1 ,4-giucosidic linkages in amyiose and amylopectins forming dextrins and maltose. It contains virtually no side activities, and was used in the form of a free-flowing, non-dusting, agglomerated powder with an average particle size of around 150 microns. The mixture was left to resolidify and was then formed into a coarse powder by passage through a metal sieve.
- the encapsulated enzyme powder was included in standard white bread dough at twice the usual level, to magnify the effects of encapsulation.
- the stickiness of the dough was compared to that of dough with the same amount of standard enzyme added. A marked decrease in dough stickiness was observed relative to the standard enzyme, and once baked the resultant loaves exhibited the full benefits of FAA addition with respect to loaf height and crumb softness.
- Example 5 Couva 700TM was melted and kept at 40°C FAA was ground in a mortar and an equal mass of the melted Couva 700TM was added The mixture was solidified and mixed with a mortar and pestle to form a powder When incorporated into doughs, a decrease in stickiness was observed in comparison to doughs with equivalent levels of standard FAA present When 2% extra water was added the dough became soft (but not sticky) and handleability was maintained In all cases there was no detrimental effect on the increased loaf height or crumb softness
- Fungal ⁇ -amylase 200 ppm of 5000 skb or its equivalent in terms of 77000 skb
- Revel F' from Loders Croklaan
- FAA fungal ⁇ -amylase
- the FAA was Fungamyl 2500 BGTM 77000skb from Novo Nordisk.
- the FAA was 20 added in 1 :9 ratio to the molten fat, and the mixture spray chilled (to effect spray crystallisation) yielding a fine powder.
- Revel FTM is a fractionated, hydrogenated, refined vegetable fat of non-lauric origin. It has a slip melting point of about 46°C and is hard at room temperature, 72% solid at 35°C.
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU56703/98A AU5670398A (en) | 1997-01-22 | 1998-01-20 | Enzyme-based bread improvers |
EP98900892A EP0966199A2 (en) | 1997-01-22 | 1998-01-20 | Enzyme-based bread improvers |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9701267.8 | 1997-01-22 | ||
GBGB9701267.8A GB9701267D0 (en) | 1997-01-22 | 1997-01-22 | Enzyme-based bread improvers |
GB9701660.4 | 1997-01-28 | ||
GBGB9701660.4A GB9701660D0 (en) | 1997-01-28 | 1997-01-28 | Enzyme-based bread improvers |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1998032336A2 true WO1998032336A2 (en) | 1998-07-30 |
WO1998032336A3 WO1998032336A3 (en) | 1998-11-19 |
Family
ID=26310842
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1998/000080 WO1998032336A2 (en) | 1997-01-22 | 1998-01-20 | Enzyme-based bread improvers |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0966199A2 (en) |
AU (1) | AU5670398A (en) |
WO (1) | WO1998032336A2 (en) |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001011975A1 (en) * | 1999-08-19 | 2001-02-22 | Horn Merritt C | Methods for preparing baked goods with addition of lipid-coated enzyme |
WO2002019828A1 (en) * | 2000-09-08 | 2002-03-14 | Novozymes A/S | A dough composition comprising a lipid-encapsulated enzyme |
EP1413202A1 (en) * | 2002-10-22 | 2004-04-28 | CSM Nederland B.V. | Lipid-encapsulated functional bakery ingredients |
WO2010029151A1 (en) * | 2008-09-11 | 2010-03-18 | Novozymes A/S | Food and beverage ingredient delivery systems |
US8354131B2 (en) | 2006-09-13 | 2013-01-15 | Kraft Foods Global Brands Llc | Microwavable food products |
US9415014B2 (en) | 2009-04-13 | 2016-08-16 | Curemark, Llc | Enzyme delivery systems and methods of preparation and use |
US9624525B2 (en) | 1999-12-17 | 2017-04-18 | Curemark, Llc | Method for treating pervasive development disorders |
US9687534B2 (en) | 2008-04-18 | 2017-06-27 | Curemark, Llc | Pharmaceutical preparation for the treatment of the symptoms of addiction and method of diagnosing same |
US9687535B2 (en) | 2008-10-03 | 2017-06-27 | Curemark, Llc | Methods and compositions for the treatment of symptoms of prion diseases |
US9895427B2 (en) | 2009-01-06 | 2018-02-20 | Galenagen, Llc | Compositions and methods for the treatment or the prevention of E. coli infections and for the eradication or reduction of E. coli surfaces |
US9925250B2 (en) | 2008-03-13 | 2018-03-27 | Curemark, Llc | Method of treating proteinuria in pregnancy |
EP1581064B1 (en) * | 2002-12-23 | 2018-08-15 | Balchem Corporation | Controlled release encapsulated bioactive substances |
US10209253B2 (en) | 2000-11-16 | 2019-02-19 | Curemark, Llc | Methods for diagnosing pervasive development disorders, dysautonomia and other neurological conditions |
US10279016B2 (en) | 2011-04-21 | 2019-05-07 | Curemark, Llc | Method of treatment of schizophreniform disorder |
US10350229B2 (en) | 2005-08-30 | 2019-07-16 | Curemark, Llc | Use of lactulose in the treatment of autism |
US10350278B2 (en) | 2012-05-30 | 2019-07-16 | Curemark, Llc | Methods of treating Celiac disease |
US10588948B2 (en) | 2008-06-26 | 2020-03-17 | Curemark, Llc | Methods and compositions for the treatment of symptoms of Williams Syndrome |
US10716835B2 (en) | 2009-10-21 | 2020-07-21 | Curemark, Llc | Methods and compositions for the prevention and treatment of influenza |
US10736946B2 (en) | 2009-01-06 | 2020-08-11 | Galenagen, Llc | Compositions and methods for treatment or prevention of Staphylococcus aureus infections and for the eradication or reduction of Staphylococcus aureus on surfaces |
US10776453B2 (en) | 2008-08-04 | 2020-09-15 | Galenagen, Llc | Systems and methods employing remote data gathering and monitoring for diagnosing, staging, and treatment of Parkinsons disease, movement and neurological disorders, and chronic pain |
CN112702918A (en) * | 2018-06-04 | 2021-04-23 | 诺维信公司 | Solid enzymatic preparation for use in baking |
US11016104B2 (en) | 2008-07-01 | 2021-05-25 | Curemark, Llc | Methods and compositions for the treatment of symptoms of neurological and mental health disorders |
US11541009B2 (en) | 2020-09-10 | 2023-01-03 | Curemark, Llc | Methods of prophylaxis of coronavirus infection and treatment of coronaviruses |
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Cited By (40)
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US6635289B2 (en) | 1999-08-19 | 2003-10-21 | Merritt C. Horn | Methods and compositions for retarding the staling of baked goods |
WO2001011975A1 (en) * | 1999-08-19 | 2001-02-22 | Horn Merritt C | Methods for preparing baked goods with addition of lipid-coated enzyme |
US9624525B2 (en) | 1999-12-17 | 2017-04-18 | Curemark, Llc | Method for treating pervasive development disorders |
US9624526B2 (en) | 1999-12-17 | 2017-04-18 | Curemark Llc | Method for treating pervasive development disorders |
WO2002019828A1 (en) * | 2000-09-08 | 2002-03-14 | Novozymes A/S | A dough composition comprising a lipid-encapsulated enzyme |
US10209253B2 (en) | 2000-11-16 | 2019-02-19 | Curemark, Llc | Methods for diagnosing pervasive development disorders, dysautonomia and other neurological conditions |
WO2004037004A3 (en) * | 2002-10-22 | 2004-10-21 | Csm Nederland Bv | Encapsulated functional bakery ingredients |
WO2004037004A2 (en) * | 2002-10-22 | 2004-05-06 | Csm Nederland B.V. | Encapsulated functional bakery ingredients |
KR100818775B1 (en) * | 2002-10-22 | 2008-04-02 | 씨에스엠 네덜란드 비.브이. | Encapsulated functional bakery ingredients |
EP1413202A1 (en) * | 2002-10-22 | 2004-04-28 | CSM Nederland B.V. | Lipid-encapsulated functional bakery ingredients |
EP1581064B1 (en) * | 2002-12-23 | 2018-08-15 | Balchem Corporation | Controlled release encapsulated bioactive substances |
US11033563B2 (en) | 2005-08-30 | 2021-06-15 | Curemark, Llc | Use of lactulose in the treatment of autism |
US10350229B2 (en) | 2005-08-30 | 2019-07-16 | Curemark, Llc | Use of lactulose in the treatment of autism |
US8354131B2 (en) | 2006-09-13 | 2013-01-15 | Kraft Foods Global Brands Llc | Microwavable food products |
US9925250B2 (en) | 2008-03-13 | 2018-03-27 | Curemark, Llc | Method of treating proteinuria in pregnancy |
US11045527B2 (en) | 2008-03-13 | 2021-06-29 | Curemark, Llc | Method of diagnosing preeclampsia or pregnancy-induced hypertension |
US9687534B2 (en) | 2008-04-18 | 2017-06-27 | Curemark, Llc | Pharmaceutical preparation for the treatment of the symptoms of addiction and method of diagnosing same |
US10272141B2 (en) | 2008-04-18 | 2019-04-30 | Curemark, Llc | Pharmaceutical preparation for the treatment of the symptoms of addiction and method of diagnosing same |
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US10776453B2 (en) | 2008-08-04 | 2020-09-15 | Galenagen, Llc | Systems and methods employing remote data gathering and monitoring for diagnosing, staging, and treatment of Parkinsons disease, movement and neurological disorders, and chronic pain |
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US10413601B2 (en) | 2008-10-03 | 2019-09-17 | Curemark, Llc | Methods and compositions for the treatment of symptoms of prion diseases |
US9687535B2 (en) | 2008-10-03 | 2017-06-27 | Curemark, Llc | Methods and compositions for the treatment of symptoms of prion diseases |
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US11357835B2 (en) | 2009-01-06 | 2022-06-14 | Galenagen, Llc | Compositions and methods for the treatment or the prevention of E. coli infections and for the eradication or reduction of E. coli surfaces |
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Also Published As
Publication number | Publication date |
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EP0966199A2 (en) | 1999-12-29 |
WO1998032336A3 (en) | 1998-11-19 |
AU5670398A (en) | 1998-08-18 |
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