US20130172547A1 - Compositions comprising c5 and c6 oligosaccharides - Google Patents

Compositions comprising c5 and c6 oligosaccharides Download PDF

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Publication number
US20130172547A1
US20130172547A1 US13/649,343 US201213649343A US2013172547A1 US 20130172547 A1 US20130172547 A1 US 20130172547A1 US 201213649343 A US201213649343 A US 201213649343A US 2013172547 A1 US2013172547 A1 US 2013172547A1
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United States
Prior art keywords
water
soluble
weight
composition
hydrolysate
Prior art date
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Abandoned
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US13/649,343
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English (en)
Inventor
Daniel Clay Floyd
Kiran Kadam
Srinivas Kilambi
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Renmatix Inc
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Renmatix Inc
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Application filed by Renmatix Inc filed Critical Renmatix Inc
Priority to US13/649,343 priority Critical patent/US20130172547A1/en
Assigned to RENMATIX, INC. reassignment RENMATIX, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: FLOYD, DANIEL C., KADAM, KIRAN L., KILAMBI, SRINIVAS
Priority to RU2012154202/15A priority patent/RU2012154202A/ru
Priority to CN201280064644.6A priority patent/CN104039803A/zh
Priority to EP20186626.6A priority patent/EP3778926A3/en
Priority to RU2012154203/04A priority patent/RU2012154203A/ru
Priority to BR112014015909A priority patent/BR112014015909B1/pt
Priority to EP17197851.3A priority patent/EP3296307B1/en
Priority to NZ625887A priority patent/NZ625887B2/en
Priority to CA2860704A priority patent/CA2860704A1/en
Priority to KR1020147020086A priority patent/KR20140108302A/ko
Priority to IN1516KON2014 priority patent/IN2014KN01516A/en
Priority to AU2012362938A priority patent/AU2012362938B2/en
Priority to SG10201610821TA priority patent/SG10201610821TA/en
Priority to BR112014015910A priority patent/BR112014015910A8/pt
Priority to EP12863319.5A priority patent/EP2797944B1/en
Priority to KR1020147020083A priority patent/KR20140108300A/ko
Priority to NZ625869A priority patent/NZ625869B2/en
Priority to JP2014550307A priority patent/JP2015503558A/ja
Priority to JP2014550308A priority patent/JP6325454B2/ja
Priority to PCT/US2012/067538 priority patent/WO2013101399A1/en
Priority to CA2817235A priority patent/CA2817235C/en
Priority to RU2014131379A priority patent/RU2014131379A/ru
Priority to PCT/US2012/067641 priority patent/WO2013101402A1/en
Priority to EP12861480.7A priority patent/EP2797943B1/en
Priority to PCT/US2012/067537 priority patent/WO2013101398A1/en
Priority to BR112014015908A priority patent/BR112014015908A8/pt
Priority to BR112014016008-2A priority patent/BR112014016008B1/pt
Priority to CA2804993A priority patent/CA2804993C/en
Priority to MYPI2014001719A priority patent/MY170912A/en
Priority to MYPI2014001714A priority patent/MY167796A/en
Priority to KR1020147020084A priority patent/KR20140108301A/ko
Priority to PCT/US2012/067644 priority patent/WO2013101403A1/en
Priority to CN201280065283.7A priority patent/CN104024268A/zh
Priority to KR1020147020085A priority patent/KR20140109441A/ko
Priority to IN1517KON2014 priority patent/IN2014KN01517A/en
Priority to AU2012362942A priority patent/AU2012362942B2/en
Publication of US20130172547A1 publication Critical patent/US20130172547A1/en
Priority to PH12014501322A priority patent/PH12014501322A1/en
Priority to PH12014501321A priority patent/PH12014501321A1/en
Assigned to RENMATIX, INC. reassignment RENMATIX, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KADAM, KIRAN L, KILAMBI, SRINIVAS, FLOYD, Daniel Clay
Priority to ZA2014/04634A priority patent/ZA201404634B/en
Priority to ZA2014/04632A priority patent/ZA201404632B/en
Priority to ZA2014/04633A priority patent/ZA201404633B/en
Priority to US14/661,000 priority patent/US9783860B2/en
Priority to US15/701,778 priority patent/US10487369B2/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/02—Monosaccharides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
    • C13B50/00—Sugar products, e.g. powdered, lump or liquid sugar; Working-up of sugar
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00—Glucose; Glucose-containing syrups
    • C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K1/00—Glucose; Glucose-containing syrups
    • C13K1/02—Glucose; Glucose-containing syrups obtained by saccharification of cellulosic materials
    • C13K1/04—Purifying
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K11/00—Fructose
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K13/00—Sugars not otherwise provided for in this class
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K13/00—Sugars not otherwise provided for in this class
    • C13K13/002—Xylose
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13K—SACCHARIDES OBTAINED FROM NATURAL SOURCES OR BY HYDROLYSIS OF NATURALLY OCCURRING DISACCHARIDES, OLIGOSACCHARIDES OR POLYSACCHARIDES
    • C13K13/00—Sugars not otherwise provided for in this class
    • C13K13/007—Separation of sugars provided for in subclass C13K
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • compositions comprising:
  • the invention is directed to methods of reducing the level of enzyme required for enzymatically hydrolyzing first water-soluble C6 saccharides having an average degree of polymerization to about 2 to about 15, preferably about 2 to about 10, and more preferably about 2 to about 6, to second water-soluble C6 saccharides having a lower average degree of polymerization than said average degree of polymerization of said first water-soluble C6 saccharides, comprising:
  • hydrolysate comprising said first water-soluble C5 saccharides and less than about 3700 ppm in total, based on total weight of water-soluble C5 saccharide hydrolysate in said composition, of elements;
  • the phrase “substantially free” means have no more than about 1%, preferably less than about 0.5%, more preferably, less than about 0.1%, by weight of a component, based on the total weight of any composition containing the component.
  • a fluid which is “supercritical” indicates a fluid which would be supercritical if present in pure form under a given set of temperature and pressure conditions.
  • “supercritical water” indicates water present at a temperature of at least about 374.2° C. and a pressure of at least about 221 bar, whether the water is pure water, or present as a mixture (e.g. water and ethanol, water and CO 2 , etc).
  • said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
  • compositions further comprise:
  • said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
  • said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
  • compositions comprising:
  • compositions further comprise:
  • compositions further comprise at least one water-soluble C6 monosaccharide hydrolysate.
  • compositions further comprise less than about 10 ppm, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of aluminum, preferably less than about 5 ppm by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of aluminum.
  • said water-soluble C6 oligosaccharides are present at a level of about 80% by weight to about 92.5% by weight, based on total weight of C6 saccharides present in said composition.
  • said water-soluble C6 oligosaccharides have a degree of polymerization of about 2 to about 13, preferably, about 2 to about 10, and more preferably about 2 to about 6.
  • the compositions further comprise about 5% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition, of C6 monosaccharides.
  • said C6 tetrasaccharides are present at a level of about 10% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition.
  • said C6 pentasaccharides are present at a level of about 10% by weight to about 20% by weight, based on total weight of C6 saccharides present in said composition.
  • compositions further comprise about 7.5% by weight to about 20% by weight, based on total weight of said water-soluble C6 oligosaccharide hydrolysate and said water-soluble C6 monosaccharide hydrolysate in said composition, of C6 monosaccharides.
  • said elements are Al, As, B, Ba, Be, Ca, Cd, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Mo, Na, Ni, P, Pb, S, Sb, Se, Si, Sn, Sr, Ti, Tl, V, and Zn.
  • compositions further comprise:
  • At least one water-soluble C5 monosaccharide hydrolysate at least one water-soluble C5 monosaccharide hydrolysate.
  • compositions further comprise less than about 2300 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of calcium, preferably less than about 2250 ppm by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of calcium.
  • the water-soluble C5 oligosaccharide hydrolysate is processed from lignocellulosic biomass using supercritical, subcritical, or near critical fluid extraction, or a combination thereof.
  • compositions comprise less than about 350 ppm of nitrogen per kg of total weight of water-soluble C5 saccharides, preferably less than about 325 ppm of nitrogen per kg of total weight of water-soluble C6 saccharides. Nitrogen may be measured by thermal conductivity detection after combustion and reduction.
  • water-soluble C5 oligosaccharides have a degree of polymerization of about 2 to about 28.
  • said water-soluble C5 oligosaccharides are present at a level of about 80% by weight to about 90% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
  • said water-soluble C5 oligosaccharides have a degree of polymerization of about 2 to about 16, preferably, about 2 to about 10, and more preferably, about 2 to about 5.
  • said water-soluble C5 oligosaccharide hydrolysate comprises:
  • said water-soluble C5 oligosaccharides have a degree of polymerization of about 2 to about 16, preferably, about 2 to about 10, and more preferably, about 2 to about 5.
  • the compositions further comprise about 10% by weight, to about 25% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of C5 monosaccharides.
  • said C5 pentasaccharides are present at a level of about 2.5% by weight to about 15% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
  • said C5 saccharides having at a degree of polymerization of at least about 6 are present at a level of about 12.5% by weight to about 30% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition.
  • compositions described herein further comprise about 10% by weight, to about 25% by weight, based on total weight of said water-soluble C5 oligosaccharide hydrolysate and said water-soluble C5 monosaccharide hydrolysate in said composition, of C5 monosaccharides.
  • compositions of the invention are preferably prepared from biomass by processes employing supercritical, subcritical, and/or near critical water, preferably without the addition of acid.
  • the processes may include pretreatment step or steps using supercritical or near critical water to separate the C5 sugars (monomers and/or oligomers) from cellulose and lignin.
  • suitable temperatures are about 130° C. to about 250° C.
  • suitable pressures are about 4 bars to about 100 bars
  • suitable residence times are about 0.5 minutes to about 5 hours.
  • the processes may also include a cellulose hydrolysis step or steps using supercritical or near critical water to separate the cellulose (which may processed to form C6 monomeric and/or oligomeric sugars) from the lignin.
  • compositions of the invention comprising C5 saccharides or C6 saccharides may be utilized in a wide variety of applications, where C5 and C6 sugars are conventionally utilized, including, but not limited to, the production of various chemicals and fuels using fermentative, enzymatic, catalytic, and non-catalytic (e.g., thermal decomposition) processes.
  • Such processes are useful for preparing feedstocks for the preparation of the following non-exhaustive list:
  • the C5 oligosaccharide and C6 oligosaccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in a two stage process.
  • Particulate lignocellulosic biomass consisting of mixed hardwood chips of 140 mesh or less was mixed with water to form a slurry (about 20% by weight solids).
  • the slurry was heated to a temperature of about 170-245° C. and then feed into a pretreatment reactor for about 1-120 minutes under sufficient pressure to keep the water in the liquid phase.
  • the pretreated slurry was then cooled to a temperature less than about 100° C. under little (less than about 10 bar) or no pressure.
  • the pretreated solids were then separated from the liquid stream using a filter press.
  • the C5 oligosaccharide and C6 oligosaccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in a two stage process as described in Example 1. The samples were then diluted ten times. The degree of polymerization was qualitatively determined, i.e., not quantifying the amount of each oligomer, using gel permeation chromatography.
  • the C5 saccharide compositions of the invention were prepared using supercritical, subcritical, and near critical water extraction in the first stage of the two stage process as described in Example 1. Representative samples bracketing the extremes/possibilities of reactor feed concentration (10.66-13.78 weight %, reactor temperature (249-261° C.), and reactor residence time (2-3 minutes) were selected.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Emergency Medicine (AREA)
  • Food Science & Technology (AREA)
  • Saccharide Compounds (AREA)
  • Fodder In General (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Extraction Or Liquid Replacement (AREA)
  • Processing Of Solid Wastes (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US13/649,343 2011-12-30 2012-10-11 Compositions comprising c5 and c6 oligosaccharides Abandoned US20130172547A1 (en)

Priority Applications (43)

Application Number Priority Date Filing Date Title
US13/649,343 US20130172547A1 (en) 2011-12-30 2012-10-11 Compositions comprising c5 and c6 oligosaccharides
IN1517KON2014 IN2014KN01517A (enrdf_load_stackoverflow) 2011-12-30 2012-12-03
AU2012362942A AU2012362942B2 (en) 2011-12-30 2012-12-03 Compositions comprising C5 and C6 oligosaccharides
RU2014131379A RU2014131379A (ru) 2011-12-30 2012-12-03 Композиции, содержащие с5 и с6 сахариды
EP12861480.7A EP2797943B1 (en) 2011-12-30 2012-12-03 Compositions comprising c6 monosaccharides
EP20186626.6A EP3778926A3 (en) 2011-12-30 2012-12-03 Compositions comprising c6 oligosaccharides
RU2012154203/04A RU2012154203A (ru) 2011-12-30 2012-12-03 Композиции, включающие с5 и с6 олигосахариды
BR112014015909A BR112014015909B1 (pt) 2011-12-30 2012-12-03 composição compreendendo oligossacarídeo c5 e c6 e hidrolisatos de monossacarídeo
EP17197851.3A EP3296307B1 (en) 2011-12-30 2012-12-03 Compositions comprising c5 oligosaccharides
NZ625887A NZ625887B2 (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 monosaccharides
CA2860704A CA2860704A1 (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 monosaccharides
KR1020147020086A KR20140108302A (ko) 2011-12-30 2012-12-03 C5 및 c6 단당류를 포함하는 조성물
IN1516KON2014 IN2014KN01516A (enrdf_load_stackoverflow) 2011-12-30 2012-12-03
AU2012362938A AU2012362938B2 (en) 2011-12-30 2012-12-03 Compositions comprising C5 and C6 monosaccharides
SG10201610821TA SG10201610821TA (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 monosaccharides
BR112014015910A BR112014015910A8 (pt) 2011-12-30 2012-12-03 composição
BR112014015908A BR112014015908A8 (pt) 2011-12-30 2012-12-03 composição
KR1020147020083A KR20140108300A (ko) 2011-12-30 2012-12-03 C5 및 c6 올리고당류를 포함하는 조성물
CN201280064644.6A CN104039803A (zh) 2011-12-30 2012-12-03 包含c5和c6单糖的组合物
JP2014550307A JP2015503558A (ja) 2011-12-30 2012-12-03 Ｃ５およびｃ６単糖を含む組成物
JP2014550308A JP6325454B2 (ja) 2011-12-30 2012-12-03 Ｃ５およびｃ６オリゴ糖を含む組成物
PCT/US2012/067538 WO2013101399A1 (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 monosaccharides
CA2817235A CA2817235C (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 oligosaccharides
RU2012154202/15A RU2012154202A (ru) 2011-12-30 2012-12-03 Композиции, включающие с5 и с6 олигосахариды
PCT/US2012/067641 WO2013101402A1 (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 oligosaccharides
PCT/US2012/067537 WO2013101398A1 (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 monosaccharides
NZ625869A NZ625869B2 (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 oligosaccharides
EP12863319.5A EP2797944B1 (en) 2011-12-30 2012-12-03 Compositions comprising c6 oligosaccharides
BR112014016008-2A BR112014016008B1 (pt) 2011-12-30 2012-12-03 Composição compreendendo oligossacarídeo c6 e hidrolisatos de monossacrídeo solúveis em água
CA2804993A CA2804993C (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 oligosaccharides
MYPI2014001719A MY170912A (en) 2011-12-30 2012-12-03 Compositions comprising c6 oligosaccharides
MYPI2014001714A MY167796A (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 monosaccharides
KR1020147020084A KR20140108301A (ko) 2011-12-30 2012-12-03 C5 및 c6 올리고당류를 포함하는 조성물
PCT/US2012/067644 WO2013101403A1 (en) 2011-12-30 2012-12-03 Compositions comprising c5 and c6 oligosaccharides
CN201280065283.7A CN104024268A (zh) 2011-12-30 2012-12-03 包含c5和c6寡糖的组合物
KR1020147020085A KR20140109441A (ko) 2011-12-30 2012-12-03 C5 및 c6 단당류를 포함하는 조성물
PH12014501321A PH12014501321A1 (en) 2011-12-30 2014-06-10 Compositions comprising c5 and c6 oligosaccharides
PH12014501322A PH12014501322A1 (en) 2011-12-30 2014-06-10 Compositions comprising c5 and c6 monosaccharides
ZA2014/04634A ZA201404634B (en) 2011-12-30 2014-06-24 Compositions comprising c5 and c6 oligosaccharides
ZA2014/04632A ZA201404632B (en) 2011-12-30 2014-06-24 Compositions comprising c5 and c6 monosaccharides
ZA2014/04633A ZA201404633B (en) 2011-12-30 2014-06-24 Compositions comprising c5 and c6 oligosaccharides
US14/661,000 US9783860B2 (en) 2011-12-30 2015-03-18 Compositions comprising C5 and C6 oligosaccharides
US15/701,778 US10487369B2 (en) 2011-12-30 2017-09-12 Compositions comprising C5 and C6 oligosaccarides

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201161581907P 2011-12-30 2011-12-30
US201161581890P 2011-12-30 2011-12-30
US201161581878P 2011-12-30 2011-12-30
US201161581922P 2011-12-30 2011-12-30
US13/649,343 US20130172547A1 (en) 2011-12-30 2012-10-11 Compositions comprising c5 and c6 oligosaccharides

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US14/661,000 Continuation US9783860B2 (en) 2011-12-30 2015-03-18 Compositions comprising C5 and C6 oligosaccharides

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US20130172547A1 true US20130172547A1 (en) 2013-07-04

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Family Applications (19)

Application Number Title Priority Date Filing Date
US13/649,294 Abandoned US20130172546A1 (en) 2011-12-30 2012-10-11 Compositions comprising c5 and c6 oligosaccharides
US13/649,343 Abandoned US20130172547A1 (en) 2011-12-30 2012-10-11 Compositions comprising c5 and c6 oligosaccharides
US13/649,437 Abandoned US20130167837A1 (en) 2011-12-30 2012-10-11 Compositions comprising c5 and c6 monosaccharides
US13/649,395 Active US8894771B2 (en) 2011-12-30 2012-10-11 Compositions comprising C5 and C6 monosaccharides
US14/659,675 Abandoned US20150184261A1 (en) 2011-12-30 2015-03-17 Compositions Comprising C5 and C6 Monosaccharides
US14/660,988 Active US9797021B2 (en) 2011-12-30 2015-03-18 Compositions comprising C5 and C6 oligosaccharides
US14/661,000 Active US9783860B2 (en) 2011-12-30 2015-03-18 Compositions comprising C5 and C6 oligosaccharides
US14/668,133 Abandoned US20150197824A1 (en) 2011-12-30 2015-03-25 Compositions comprising c5 and c6 monosaccharides
US15/701,778 Active US10487369B2 (en) 2011-12-30 2017-09-12 Compositions comprising C5 and C6 oligosaccarides
US15/827,486 Abandoned US20180080093A1 (en) 2011-12-30 2017-11-30 Compositions comprising c5 and c6 monosaccharides
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US14/668,133 Abandoned US20150197824A1 (en) 2011-12-30 2015-03-25 Compositions comprising c5 and c6 monosaccharides
US15/701,778 Active US10487369B2 (en) 2011-12-30 2017-09-12 Compositions comprising C5 and C6 oligosaccarides
US15/827,486 Abandoned US20180080093A1 (en) 2011-12-30 2017-11-30 Compositions comprising c5 and c6 monosaccharides
US15/949,858 Abandoned US20180230560A1 (en) 2011-12-30 2018-04-10 COMPOSITIONS COMPRISING C5 and C6 MONOSACCHARIDES
US15/949,878 Abandoned US20180230561A1 (en) 2011-12-30 2018-04-10 COMPOSITIONS COMPRISING C5 and C6 MONOSACCHARIDES
US15/949,825 Abandoned US20180230559A1 (en) 2011-12-30 2018-04-10 COMPOSITIONS COMPRISING C5 and C6 MONOSACCHARIDES
US16/212,944 Abandoned US20190106756A1 (en) 2011-12-30 2018-12-07 COMPOSITIONS COMPRISING C5 and C6 MONOSACCHARIDES
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IN2014KN01517A (enrdf_load_stackoverflow) 2015-10-23
BR112014016008A2 (pt) 2017-06-13
PH12014501322B1 (en) 2014-09-15
US20180066328A1 (en) 2018-03-08
US20190338379A1 (en) 2019-11-07
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US9783860B2 (en) 2017-10-10
US20190106756A1 (en) 2019-04-11
BR112014015908A2 (pt) 2017-06-13
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US20150191500A1 (en) 2015-07-09
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