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WO2014086373A1 - Cristallisation d'oligosaccharides de lait humain - Google Patents

Cristallisation d'oligosaccharides de lait humain Download PDF

Info

Publication number
WO2014086373A1
WO2014086373A1 PCT/DK2013/050416 DK2013050416W WO2014086373A1 WO 2014086373 A1 WO2014086373 A1 WO 2014086373A1 DK 2013050416 W DK2013050416 W DK 2013050416W WO 2014086373 A1 WO2014086373 A1 WO 2014086373A1
Authority
WO
WIPO (PCT)
Prior art keywords
hmo
acidic
alcohol solution
alcohol
drying
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/DK2013/050416
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English (en)
Inventor
Gyula Dekany
Markus Hederos
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Glycom AS
Original Assignee
Glycom AS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Glycom AS filed Critical Glycom AS
Publication of WO2014086373A1 publication Critical patent/WO2014086373A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • 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
    • 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
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • HMOs could be isolated in crystalline form from the aqueous enzymatic or fermentation media, in which the HMOs were produced, that would provide a simple and cheap method to separate the HMOs from contaminants in such aqueous media and obtain the HMOs as pure products. Indeed, purification and isolation by crystallization generally makes any process more attractive and cost-effective industrially. See EP-A-1405856. However, there has, to date, been no commercially suitable method for purifying and isolating, by crystallization, HMOs produced enzymatically or by fermentation.
  • non-acidic preferably refers to a compound containing no carboxyl group, e.g., no sialic acid group.
  • non-acidic human milk oligosaccharide or “non- acidic HMO” preferably means a compound with one of the following core structures or desialylated analogs thereof:
  • Particularly preferred non-acidic HMOs include:
  • non-acidic precursor of a human milk oligosaccharide or “non-acidic HMO precursor” preferably means fucose, N-acetyl glucosamine, galactose, N-acetyl lactosamine, lacto-N-biose or lacto-N-triose II.
  • the dry, preferably protein-free powder is then treated with a hot, preferably boiling, d-C 6 alcohol solvent, preferably a CrC 4 alcohol solvent, especially methanol, to produce an alcohol solution of the non-acidic HMO or HMO precursor.
  • a hot, preferably boiling, d-C 6 alcohol solvent preferably a CrC 4 alcohol solvent, especially methanol
  • the alcohol solvent can, if desired, be heated, preferably to boiling, only after it is used to dissolve the non-acidic HMO or HMO precursor to produce the alcohol solution.
  • non-acidic HMOs and precursors are crystallized in essentially the same manner after fermentation thereof: lacto-N-triose II (US 7521212, Priem et al. Glycobiology 12, 235 [2002]), LNnT( US 7521212, or Priem et al. Glycobiology ⁇ 2, 235 [2002]),

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

La présente invention porte sur un procédé d'obtention d'un oligosaccharide du lait humain (HMO) non acide ou d'un précurseur de celui-ci sous forme cristalline à partir d'un milieu aqueux, tel qu'un bouillon de fermentation, par séchage du milieu aqueux suivi d'un traitement de celui-ci avec un solvant alcoolique C1-C6 chaud.
PCT/DK2013/050416 2012-12-07 2013-12-05 Cristallisation d'oligosaccharides de lait humain Ceased WO2014086373A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DKPA201270770 2012-12-07
DKPA201270770 2012-12-07

Publications (1)

Publication Number Publication Date
WO2014086373A1 true WO2014086373A1 (fr) 2014-06-12

Family

ID=49841470

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DK2013/050416 Ceased WO2014086373A1 (fr) 2012-12-07 2013-12-05 Cristallisation d'oligosaccharides de lait humain

Country Status (1)

Country Link
WO (1) WO2014086373A1 (fr)

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015188834A1 (fr) * 2014-06-11 2015-12-17 Glycom A/S Séparation du 2'-o-fucosyllactose contenu dans un bouillon de fermentation
WO2016086947A1 (fr) * 2014-12-05 2016-06-09 Glycom A/S Difucosyllactose cristallin
WO2016095924A1 (fr) 2014-12-16 2016-06-23 Glycom A/S Séparation de 2'-fl d'un bouillon de fermentation
WO2017101953A1 (fr) * 2015-12-17 2017-06-22 Glycom A/S Formes cristallines de lnt
WO2017182965A1 (fr) * 2016-04-19 2017-10-26 Glycom A/S Séparation d'oligosaccharides d'un bouillon de fermentation
WO2017221208A1 (fr) 2016-06-24 2017-12-28 Glycom A/S Composés comprenant des hmos pour la prévention et/ou le traitement d'infections virales et/ou bactériennes.
WO2018077368A1 (fr) 2016-10-31 2018-05-03 Glycom A/S Procédé d'élimination de solvant organique résiduel d'un oligosaccharide cristallin
EP3494806A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Lacto-n-fucopentaose séché par pulvérisation
EP3494804A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH 3-fucosyllactose séché en pulvérisation
EP3494805A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Tétrasaccharide séché en pulvérisation
EP3494807A1 (fr) * 2017-12-11 2019-06-12 Jennewein Biotechnologie GmbH Sialyllactose séché par pulvérisation
WO2019110801A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh 3-fucosyllactose séché par atomisation
US10407516B2 (en) * 2016-10-31 2019-09-10 Glycom A/S Crystalline HMO
EP3546060A1 (fr) * 2018-03-27 2019-10-02 DuPont Nutrition Biosciences ApS Procédé de séchage par pulvérisation de solutions de fucosyllactose et de compositions de produit correspondantes
WO2019189200A1 (fr) 2018-03-29 2019-10-03 森永乳業株式会社 Composition nutritionnelle, composition alimentaire/de boisson utilisant la composition nutritionnelle et poudre de lait modifiée utilisant la composition nutritionnelle
EP3131912B1 (fr) 2014-01-20 2020-01-22 Jennewein Biotechnologie GmbH Procede de purification efficace d' oligosaccharides neutres du lait humain (hmo) a partir de la fermentation microbienne
WO2020079114A1 (fr) 2018-10-18 2020-04-23 Basf Se Procédé d'obtention de 2'-fucosyllactose cristallin
EP3750902A1 (fr) * 2019-06-14 2020-12-16 Jennewein Biotechnologie GmbH Procede de purification de lacto-n-neotetraose
WO2021181349A1 (fr) 2020-03-12 2021-09-16 Glycom A/S Cristallisation du 2'-fl
US11505567B2 (en) 2017-07-12 2022-11-22 Glycom A/S Amorphous mixture comprising a neutral mono- or oligosaccharide and an acidic non-carbohydrate component
CN115873051A (zh) * 2022-05-17 2023-03-31 山东恒鲁生物科技有限公司 三糖的新晶型
RU2793915C1 (ru) * 2019-06-14 2023-04-10 Хр. Ханзен ХМО ГмбХ Способ очистки лакто-n-неотетраозы
CN116425810A (zh) * 2023-06-14 2023-07-14 山东合成远景生物科技有限公司 一种混合液中3-岩藻糖基乳糖的纯化方法
CN116462720A (zh) * 2023-04-22 2023-07-21 山东恒鲁生物科技有限公司 一种二糖的晶体
CN117003803A (zh) * 2022-05-07 2023-11-07 山东恒鲁生物科技有限公司 一种三糖的新晶型

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WO2001004341A1 (fr) 1999-07-07 2001-01-18 Centre National De La Recherche Scientifique (Cnrs) Procede de production d'oligosaccharides
EP1405856A1 (fr) 2001-06-11 2004-04-07 Kyowa Hakko Kogyo Co., Ltd Cristaux d'oligosaccharides et procedes de preparation correspondants
WO2010070104A1 (fr) 2008-12-19 2010-06-24 Jennewein Biotechnologie Gmbh Synthèse de composés fucosylés
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WO2011150939A1 (fr) * 2010-06-01 2011-12-08 Glycom A/S Formes polymorphiques du 2'-o-fucosyllactose et leurs procédés de production
WO2012112777A2 (fr) 2011-02-16 2012-08-23 Glycosyn LLC Biosynthèse d'oligosaccharides de lait humain dans des bactéries manipulées

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EP1194584A1 (fr) 1999-07-07 2002-04-10 Centre National De La Recherche Scientifique (Cnrs) Procede de production d'oligosaccharides
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WO2011100980A1 (fr) * 2010-02-19 2011-08-25 Glycom A/S Procédé pour la préparation du tétrasaccharide lacto-n-néotétraose (lnnt) contenant de la n-acétyllactosamine
WO2011150939A1 (fr) * 2010-06-01 2011-12-08 Glycom A/S Formes polymorphiques du 2'-o-fucosyllactose et leurs procédés de production
WO2012112777A2 (fr) 2011-02-16 2012-08-23 Glycosyn LLC Biosynthèse d'oligosaccharides de lait humain dans des bactéries manipulées

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Cited By (73)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11597740B2 (en) 2014-01-20 2023-03-07 Chr. Hansen HMO GmbH Process for efficient purification of neutral human milk oligosaccharides (HMOs) from microbial fermentation
EP3680249B1 (fr) 2014-01-20 2023-03-01 Chr. Hansen HMO GmbH Procédé de purification efficace d' oligosaccharides neutres du lait humain (hmos) à partir de la fermentation microbienne
EP3686211B1 (fr) 2014-01-20 2023-03-01 Chr. Hansen HMO GmbH Procédé permettant de purifier efficacement des oligosaccharides du lait humain neutre (hmos) à partir de la fermentation microbienne
EP3131912B1 (fr) 2014-01-20 2020-01-22 Jennewein Biotechnologie GmbH Procede de purification efficace d' oligosaccharides neutres du lait humain (hmo) a partir de la fermentation microbienne
US11661435B2 (en) 2014-01-20 2023-05-30 Chr. Hansen HMO GmbH Spray-dried, high-purity, neutral human milk oligosaccharides (HMOs) from microbial fermentation
WO2015188834A1 (fr) * 2014-06-11 2015-12-17 Glycom A/S Séparation du 2'-o-fucosyllactose contenu dans un bouillon de fermentation
WO2016086947A1 (fr) * 2014-12-05 2016-06-09 Glycom A/S Difucosyllactose cristallin
US10500221B2 (en) 2014-12-05 2019-12-10 Glycom A/S Crystalline difucosyllactose
EP3227309A4 (fr) * 2014-12-05 2019-01-16 Glycom A/S Difucosyllactose cristallin
US10676770B2 (en) 2014-12-16 2020-06-09 Glycom A/S Separation of 2′-FL from a fermentation broth
EP4151645A2 (fr) 2014-12-16 2023-03-22 Glycom A/S Séparation de 2'-fl d'un bouillon de fermentation
US12060594B2 (en) 2014-12-16 2024-08-13 Glycom A/S Separation of 2′-FL from a fermentation broth
WO2016095924A1 (fr) 2014-12-16 2016-06-23 Glycom A/S Séparation de 2'-fl d'un bouillon de fermentation
US11267839B2 (en) 2015-12-17 2022-03-08 Glycom A/S Crystalline forms of LNT
US11767340B2 (en) 2015-12-17 2023-09-26 Glycom A/S Crystalline forms of LNT
US10696705B2 (en) 2015-12-17 2020-06-30 Glycom A/S Crystalline forms of LNT
WO2017101953A1 (fr) * 2015-12-17 2017-06-22 Glycom A/S Formes cristallines de lnt
WO2017182965A1 (fr) * 2016-04-19 2017-10-26 Glycom A/S Séparation d'oligosaccharides d'un bouillon de fermentation
US11312741B2 (en) 2016-04-19 2022-04-26 Glycom A/S Separation of oligosaccharides from fermentation broth
WO2017221208A1 (fr) 2016-06-24 2017-12-28 Glycom A/S Composés comprenant des hmos pour la prévention et/ou le traitement d'infections virales et/ou bactériennes.
EP3474861A4 (fr) * 2016-06-24 2020-04-15 Glycom A/S Composés comprenant des hmos pour la prévention et/ou le traitement d'infections virales et/ou bactériennes.
WO2018077368A1 (fr) 2016-10-31 2018-05-03 Glycom A/S Procédé d'élimination de solvant organique résiduel d'un oligosaccharide cristallin
US10407516B2 (en) * 2016-10-31 2019-09-10 Glycom A/S Crystalline HMO
US11384110B2 (en) 2016-10-31 2022-07-12 Glycom A/S Method for removing residual organic solvent from a crystalline oligosaccharide
US11939351B2 (en) 2017-07-12 2024-03-26 Glycom A/S Amorphous mixture comprising a neutral mono- or oligosaccharide and an acidic non-carbohydrate component
US11505567B2 (en) 2017-07-12 2022-11-22 Glycom A/S Amorphous mixture comprising a neutral mono- or oligosaccharide and an acidic non-carbohydrate component
US12054513B2 (en) 2017-07-12 2024-08-06 Glycom A/S Amorphous mixture comprising a neutral mono- or oligosaccharide and an acidic non-carbohydrate component
WO2019110804A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh Tétrasaccharides séchés par atomisation
EP3494806A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Lacto-n-fucopentaose séché par pulvérisation
EP3720298A1 (fr) * 2017-12-08 2020-10-14 Jennewein Biotechnologie GmbH 3-fucosyllactose séché par atomisation
JP2023182675A (ja) * 2017-12-08 2023-12-26 クリスチャン・ハンセン・ハーエムオー・ゲーエムベーハー 噴霧乾燥四糖
CN111447844A (zh) * 2017-12-08 2020-07-24 詹尼温生物技术有限责任公司 喷雾干燥的四糖
CN111432663A (zh) * 2017-12-08 2020-07-17 詹尼温生物技术有限责任公司 喷雾干燥的乳-n-岩藻戊糖
JP2021505174A (ja) * 2017-12-08 2021-02-18 イェンネワイン バイオテクノロジー ゲーエムベーハーＪｅｎｎｅｗｅｉｎ Ｂｉｏｔｅｃｈｎｏｌｏｇｉｅ ＧｍｂＨ 噴霧乾燥ラクト−ｎ−フコペンタオース
JP2021505177A (ja) * 2017-12-08 2021-02-18 イェンネワイン バイオテクノロジー ゲーエムベーハーＪｅｎｎｅｗｅｉｎ Ｂｉｏｔｅｃｈｎｏｌｏｇｉｅ ＧｍｂＨ 噴霧乾燥四糖
AU2018380959B2 (en) * 2017-12-08 2024-12-12 Chr. Hansen HMO GmbH Spray-dried sialyllactose
EP3494805A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Tétrasaccharide séché en pulvérisation
RU2810298C2 (ru) * 2017-12-08 2023-12-26 Хр. Ханзен ХМО ГмбХ Высушенная распылением 3-фукозиллактоза
AU2018380960B2 (en) * 2017-12-08 2025-01-02 Chr. Hansen HMO GmbH Spray-dried tetrasaccharides
RU2812853C2 (ru) * 2017-12-08 2024-02-02 Хр. Ханзен ХМО ГмбХ Высушенные распылением тетрасахариды
EP3494804A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH 3-fucosyllactose séché en pulvérisation
WO2019110803A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh Sialyllactose séché par atomisation
RU2812864C2 (ru) * 2017-12-08 2024-02-05 Хр. Ханзен ХМО ГмбХ Высушенная распылением лакто-n-фукопентаоза
WO2019110806A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh Lacto-n-fucopentaose séché par pulvérisation
US11582994B2 (en) 2017-12-08 2023-02-21 Chr. Hansen HMO GmbH Spray-dried 3-fucosyllactose
WO2019110801A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh 3-fucosyllactose séché par atomisation
CN111465331A (zh) * 2017-12-08 2020-07-28 詹尼温生物技术有限责任公司 喷雾干燥的3-岩藻糖基乳糖
EP3494807A1 (fr) * 2017-12-11 2019-06-12 Jennewein Biotechnologie GmbH Sialyllactose séché par pulvérisation
EP3755819A4 (fr) * 2018-02-19 2021-12-29 DuPont Nutrition Biosciences ApS Procédé de séchage par pulvérisation de solutions de fucosyllactose et compositions de produit associées
CN112020568A (zh) * 2018-02-19 2020-12-01 杜邦营养生物科学有限公司 用于喷雾干燥岩藻糖基乳糖溶液的方法及相关产品组合物
EP3546060A1 (fr) * 2018-03-27 2019-10-02 DuPont Nutrition Biosciences ApS Procédé de séchage par pulvérisation de solutions de fucosyllactose et de compositions de produit correspondantes
WO2019189200A1 (fr) 2018-03-29 2019-10-03 森永乳業株式会社 Composition nutritionnelle, composition alimentaire/de boisson utilisant la composition nutritionnelle et poudre de lait modifiée utilisant la composition nutritionnelle
US12022844B2 (en) 2018-03-29 2024-07-02 Morinaga Milk Industry Co., Ltd. Nutritional composition, food/drink composition using nutritional composition, and modified milk powder using nutritional composition
CN113227112A (zh) * 2018-10-18 2021-08-06 巴斯夫欧洲公司 获得晶体2′-岩藻糖基乳糖的方法
US11685759B2 (en) 2018-10-18 2023-06-27 Basf Se Method for obtaining crystalline 2′-fucosyllactose
WO2020079114A1 (fr) 2018-10-18 2020-04-23 Basf Se Procédé d'obtention de 2'-fucosyllactose cristallin
WO2020079146A1 (fr) 2018-10-18 2020-04-23 Basf Se Forme cristalline ii du 2'-o-fucosyllactose, son procédé de préparation, formulation nutritionnelle, cosmétique ou pharmaceutique le contenant
WO2020249584A1 (fr) * 2019-06-14 2020-12-17 Jennewein Biotechnologie Gmbh Procédé pour la purification du lacto-n-néotétraose
EP3750902A1 (fr) * 2019-06-14 2020-12-16 Jennewein Biotechnologie GmbH Procede de purification de lacto-n-neotetraose
RU2793915C1 (ru) * 2019-06-14 2023-04-10 Хр. Ханзен ХМО ГмбХ Способ очистки лакто-n-неотетраозы
JP2022537956A (ja) * 2019-06-14 2022-08-31 クリスチャン・ハンセン・ハーエムオー・ゲーエムベーハー ラクト－ｎ－ネオテトラオースの精製法
CN113966338A (zh) * 2019-06-14 2022-01-21 科汉森母乳低聚糖股份有限公司 纯化乳-n-新四糖的方法
AU2020291784B2 (en) * 2019-06-14 2025-07-24 Chr. Hansen HMO GmbH Process for the purification of lacto-n-neotetraose
US12479878B2 (en) 2020-03-12 2025-11-25 Glycom A/S Crystallization of 2′-FL
WO2021181349A1 (fr) 2020-03-12 2021-09-16 Glycom A/S Cristallisation du 2'-fl
CN117003803A (zh) * 2022-05-07 2023-11-07 山东恒鲁生物科技有限公司 一种三糖的新晶型
EP4431518A4 (fr) * 2022-05-07 2025-05-21 Shandong Henglu Biotech. Co., Ltd. Nouvelle forme cristalline de trisaccharide
CN115873051A (zh) * 2022-05-17 2023-03-31 山东恒鲁生物科技有限公司 三糖的新晶型
CN115873051B (zh) * 2022-05-17 2024-06-25 山东恒鲁生物科技有限公司 三糖的新晶型
WO2023221758A1 (fr) * 2022-05-17 2023-11-23 山东恒鲁生物科技有限公司 Nouvelle forme cristalline de trisaccharide
CN116462720A (zh) * 2023-04-22 2023-07-21 山东恒鲁生物科技有限公司 一种二糖的晶体
CN116425810A (zh) * 2023-06-14 2023-07-14 山东合成远景生物科技有限公司 一种混合液中3-岩藻糖基乳糖的纯化方法
CN116425810B (zh) * 2023-06-14 2023-08-11 山东合成远景生物科技有限公司 一种混合液中3-岩藻糖基乳糖的纯化方法

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