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

Cristallisation d'oligosaccharides de lait humain Download PDF

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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
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WO
WIPO (PCT)
Prior art keywords
hmo
acidic
alcohol solution
alcohol
drying
Prior art date
Application number
PCT/DK2013/050416
Other languages
English (en)
Inventor
Gyula Dekany
Markus Hederos
Original Assignee
Glycom A/S
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 A/S filed Critical Glycom A/S
Publication of WO2014086373A1 publication Critical patent/WO2014086373A1/fr

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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]),

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 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 WO2014086373A1 (fr) 2012-12-07 2013-12-05 Cristallisation d'oligosaccharides de lait humain

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WO (1) WO2014086373A1 (fr)

Cited By (22)

* 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
EP3494805A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Tétrasaccharide séché en pulvérisation
EP3494804A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH 3-fucosyllactose séché en pulvérisation
EP3494807A1 (fr) * 2017-12-11 2019-06-12 Jennewein Biotechnologie GmbH Sialyllactose séché par pulvérisation
EP3494806A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Lacto-n-fucopentaose séché par pulvérisation
WO2019110803A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh Sialyllactose 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
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
EP3750902A1 (fr) * 2019-06-14 2020-12-16 Jennewein Biotechnologie GmbH Procede de purification de lacto-n-neotetraose
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

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US11661435B2 (en) 2014-01-20 2023-05-30 Chr. Hansen HMO GmbH Spray-dried, high-purity, neutral human milk oligosaccharides (HMOs) from microbial fermentation
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
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
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
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
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
EP3227309A4 (fr) * 2014-12-05 2019-01-16 Glycom A/S Difucosyllactose cristallin
US10500221B2 (en) 2014-12-05 2019-12-10 Glycom A/S Crystalline difucosyllactose
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
WO2016095924A1 (fr) 2014-12-16 2016-06-23 Glycom A/S Séparation de 2'-fl d'un bouillon de fermentation
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
US11267839B2 (en) 2015-12-17 2022-03-08 Glycom A/S Crystalline forms of 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.
WO2018077368A1 (fr) 2016-10-31 2018-05-03 Glycom A/S Procédé d'élimination de solvant organique résiduel d'un oligosaccharide cristallin
US11384110B2 (en) 2016-10-31 2022-07-12 Glycom A/S Method for removing residual organic solvent from a crystalline oligosaccharide
US10407516B2 (en) * 2016-10-31 2019-09-10 Glycom A/S Crystalline HMO
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
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
WO2019110804A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh Tétrasaccharides séchés par atomisation
RU2812853C2 (ru) * 2017-12-08 2024-02-02 Хр. Ханзен ХМО ГмбХ Высушенные распылением тетрасахариды
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
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
EP3494806A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Lacto-n-fucopentaose séché par pulvérisation
EP3494805A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH Tétrasaccharide séché en pulvérisation
RU2812864C2 (ru) * 2017-12-08 2024-02-05 Хр. Ханзен ХМО ГмбХ Высушенная распылением лакто-n-фукопентаоза
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
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
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
WO2019110803A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh Sialyllactose séché par atomisation
WO2019110806A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh Lacto-n-fucopentaose séché par pulvérisation
RU2810298C2 (ru) * 2017-12-08 2023-12-26 Хр. Ханзен ХМО ГмбХ Высушенная распылением 3-фукозиллактоза
EP3494804A1 (fr) * 2017-12-08 2019-06-12 Jennewein Biotechnologie GmbH 3-fucosyllactose séché en pulvérisation
WO2019110801A1 (fr) * 2017-12-08 2019-06-13 Jennewein Biotechnologie Gmbh 3-fucosyllactose séché par atomisation
US11582994B2 (en) 2017-12-08 2023-02-21 Chr. Hansen HMO GmbH Spray-dried 3-fucosyllactose
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
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
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
WO2020079114A1 (fr) 2018-10-18 2020-04-23 Basf Se Procédé d'obtention de 2'-fucosyllactose cristallin
RU2793915C1 (ru) * 2019-06-14 2023-04-10 Хр. Ханзен ХМО ГмбХ Способ очистки лакто-n-неотетраозы
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
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
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
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
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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