benzyl O-β-D-galactopyranosyl-(1->3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside | 875712-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-β-D-galactopyranosyl-(1->3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside
• 英文别名: benzyl β-lacto-N-tetraoside；1-O-benzyl-β-LNT；lacto-N-tetraose-β-OBn；LNT-β-OBn；1-O-benzyl-LNT；LNT-OBn；Gal(b1-3)GlcNAc(b1-3)Gal(b1-4)Glc(b)-O-Bn；N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 875712-82-6
• 化学式: C₃₃H₅₁NO₂₁
• 分子量: 797.762
• InChiKey: UZNOYMAOEHDKMT-BJGDADBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.9
• 重原子数：
  55
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  346
• 氢给体数：
  13
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  benzyl O-β-D-galactopyranosyl-(1->3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 水 为溶剂， 50.0 ℃ 、400.01 kPa 条件下， 反应 1.5h， 以78%的产率得到lacto-N-tetraose
  参考文献：
  名称：

  SYNTHESIS OF HMO CORE STRUCTURES

  摘要：

  该发明涉及一种制备HMO核心结构前体的方法，包括将N-乙酰乳糖胺或乳酸-N-生物糖衍生物供体与乳糖或N-乙酰乳糖胺衍生物受体反应的步骤，其中供体是氧杂环丙烯供体。

  公开号：

  US20140235850A1
• 作为产物：
  描述：

  benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 在 乙二胺 、 乙酸酐 、 三乙胺 作用下， 以 乙醇 、 甲醇 为溶剂， 反应 23.0h， 以86.5%的产率得到benzyl O-β-D-galactopyranosyl-(1->3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of the 3-sulfated Lewisa pentasaccharide

  摘要：

  The sulfated pentasaccharide benzyl O-(3-O-sulfo-beta-D-galactopyranosyl)-(1 -> 3)-O-[(alpha-L-fucopyranosyl)-(1 -> 4)]-O-(2-acetamido -2-deoxy-beta-D-glucopyranosyl)-(1 -> 3)-O-(beta-D-galactopyranosyl)-(1 -> 4)-O-beta-D-glucopyranoside sodium salt was synthesized using a chemo-enzymatic approach. Lacto-N-tetraose, obtained from two disaccharides [4-metboxybenzyl O-(2,3,4,6-tetra- O-acetyl-beta-D-galactopranosyl)-(1 -> 3)-4,6-O-benzylidene-2-deoxy-2-phtalimido-beta-D-glucopyranoside and benzyl 2,6-di-O-acetyl -beta-D-galactopyranosyl-(1 -> 4)-2,3,6-tri -O-acetyl-beta-D-glucopyranoside], was regioselectively sulfated at the 3 OH position of the terminal galactose using the stannylene procedure. The fucosylation of the sulfated tetrasaccharide was performed using soluble or immobilized fucosyltransferase FucT-III to give the title compound. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.004

文献信息

• [EN] A METHOD FOR OBTAINING CRYSTALLINE LACTO-N-TETRAOSE AND LACTO-N-NEOTETRAOSE PRECURSORS AND MIXTURES THEREOF<br/>[FR] PROCÉDÉ POUR OBTENIR DES PRÉCURSEURS DE LACTO-N-TÉTRAOSE ET DE LACTO-N-NEOTÉTRAOSE CRISTALLIN ET DES MÉLANGES DE CEUX-CI
  申请人：GLYCOM AS

  公开号：WO2013091660A1

  公开（公告）日：2013-06-27

  A mixture of, preferably a mixture consisting essentially of, an lacto-N-tetraose (LNT) precursor (1) and an lacto-N-neotetraose (LNnT) precursor (2), (formula 1, 2), where R is a group removable by hydrogenolysis and R3 is either a group removable by hydrogenolysis or H, a method of crystallizing 1 and/or 2 from said mixture, and the use of said mixture for making a mixture consisting essentially of LNnT and LNT for use as a pharmaceutically or nutritionally active ingredient. The precursors can be made by reacting an acceptor of formula 5, (formula 5), wherein R is a group removable by hydrogenolysis, R1 is acyl, Ri is acyl or H, R3 is selected from a group removable by hydrogenolysis, acyl, silyl and an acetal type group and Y is selected from alkanoylamido, haloalkanoylamido, -NAc2, benzamido, alkoxycarbonylamino, haloalkoxycarbonylamino, benzyloxycarbonylamino, azido, phthalimido, tetrachlorophthalimido, 2,3- diphenylmaleimido and 2,3-dimethylmaleimido, with a donor of formula 6, (formula 6), wherein R4 is acyl and Xi is selected from halogen, -OC(=NH)CCl3, -OAc, -OBz or -SR5, wherein R5 is selected from alkyl, substituted phenyl and unsubstituted phenyl, followed by one or more deprotection steps.

  一种混合物，优选基本上由乳糖-N-四糖（LNT）前体（1）和乳糖-N-新四糖（LNnT）前体（2）（式1，2）组成，其中R是通过氢解可移除的基团，R3是可通过氢解移除的基团或H，从该混合物中结晶1和/或2的方法，以及该混合物用于制备基本上由LNnT和LNT组成的混合物，作为药用或营养活性成分的用途。这些前体可以通过反应一个受体式5（式5），其中R是通过氢解可移除的基团，R1是酰基，Ri是酰基或H，R3是从可通过氢解移除的基团、酰基、硅基和缩醛型基团中选择的，Y是从烷酰胺基、卤代烷酰胺基、-NAc2、苯甲酰胺基、烷氧羰基氨基、卤代烷氧羰基氨基、苄氧羰基氨基、叠氮基、邻苯二甲酰亚胺基、四氯邻苯二甲酰亚胺基、2,3-二苯基马来酰亚胺基和2,3-二甲基马来酰亚胺基中选择的，与一个供体式6（式6）反应，其中R4是酰基，Xi是从卤素、-OC(=NH)CCl3、-OAc、-OBz或-SR5中选择的，其中R5是从烷基、取代的苯基和未取代的苯基中选择的，随后进行一个或多个脱保护步骤来制备。
• [EN] SYNTHESIS OF HMO CORE STRUCTURES<br/>[FR] SYNTHÈSE DE STRUCTURES À NOYAU HMO
  申请人：GLYCOM AS

  公开号：WO2013044928A1

  公开（公告）日：2013-04-04

  The invention relates to a method for making precursors of HMO core structures comprising a step of reacting an N-acetyllactosamine or lacto-N-biose derivative donor with a lactose or N-acetyllactosamine derivative acceptor, wherein the donor is an oxazoline donor.

  该发明涉及一种制备HMO核心结构前体的方法，包括以下步骤：将N-乙酰乳糖胺或乳酸-N-双糖衍生物供体与乳糖或N-乙酰乳糖胺衍生物受体反应，其中供体是一种噁唑烷供体。
• Characterization and synthetic application of a novel β1,3-galactosyltransferase from Escherichia coli O55:H7
  作者：Xian-wei Liu、Chengfeng Xia、Lei Li、Wan-yi Guan、Nicholas Pettit、Hou-cheng Zhang、Min Chen、Peng George Wang

  DOI：10.1016/j.bmc.2009.06.005

  日期：2009.7

  A beta 1,3-galactosyltransferase (WbgO) was identified in Escherichia coli O55:H7. Its function was confirmed by radioactive activity assay and structure analysis of the disaccharide synthesized with the recombinant enzyme. WbgO requires a divalent metal ion, either Mn2+ or Mg2+, for its activity and is active between pH 6.0-8.0 with a pH optimum of 7.0. N-acetylglucosamine (GlcNAc) and oligosaccharides with GlcNAc at the non-reducing end were shown to be its preferred substrates and it can be used for the synthesis of type 1 glycan chains from these substrates. Together with a recombinant bacterial GlcNAc-transferase, benzyl beta-lacto-N-tetraoside was synthesized with the purified WbgO to demonstrate the synthetic utility of WbgO. (C) 2009 Elsevier Ltd. All rights reserved.
• [EN] DERIVATIZATION OF OLIGOSACCHARIDES<br/>[FR] DÉRIVATION D'OLIGOSACCHARIDES
  申请人：GLYCOM AS

  公开号：WO2012007585A9

  公开（公告）日：2012-07-26
• SYNTHESIS OF HMO CORE STRUCTURES
  申请人：Glycom A/S

  公开号：US20140235850A1

  公开（公告）日：2014-08-21

  The invention relates to a method for making precursors of HMO core structures comprising a step of reacting an N-acetyllactosamine or lacto-N-biose derivative donor with a lactose or N-acetyllactosamine derivative acceptor, wherein the donor is an oxazoline donor.

  该发明涉及一种制备HMO核心结构前体的方法，包括将N-乙酰乳糖胺或乳酸-N-生物糖衍生物供体与乳糖或N-乙酰乳糖胺衍生物受体反应的步骤，其中供体是氧杂环丙烯供体。