2-propenyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside | 389119-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-propenyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside
• 英文别名: allyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]-6-prop-2-enoxyoxane-3,5-diol
• CAS: 389119-56-6
• 化学式: C₁₇H₂₄O₇
• 分子量: 340.373
• InChiKey: ZRJLSOLTCSHHCA-BPKGMFCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-propenyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside 在 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 (2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol
  参考文献：
  名称：

  Synthesis of a set of di- and tri-sulfated galabioses

  摘要：

  Among cell-adhesion molecules, L-selectin recognizes sulfated sLe(x) with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLe(x). As a strategy to obtain 3',6',6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4',6'-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield alpha and beta anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3',6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00222-1
• 作为产物：
  描述：

  allyl 4,6-O-benzylidene-β-D-galactopyranoside 在 四丁基碘化铵 、 溶剂黄146 作用下， 反应 0.83h， 生成 2-propenyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a set of di- and tri-sulfated galabioses

  摘要：

  Among cell-adhesion molecules, L-selectin recognizes sulfated sLe(x) with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLe(x). As a strategy to obtain 3',6',6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4',6'-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield alpha and beta anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3',6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00222-1

文献信息

• Convergent Synthesis of Oligosaccharides Structurally Related to Galactan I and Galactan II of<i>Klebsiella Pneumoniae</i>and their Use in Screening of Antibody Specificity
  作者：Dmitry A. Argunov、Anastasiia S. Trostianetskaia、Vadim B. Krylov、Ekaterina A. Kurbatova、Nikolay E. Nifantiev

  DOI：10.1002/ejoc.201900389

  日期：2019.7.14

  The synthesis of di‐, tetra‐, and hexasaccharides corresponding to galactan I and galactan II of K. pneumoniae LPS O‐chain, and its application for anti‐K. pneumoniae sera screening are described.

  描述了对应于肺炎克雷伯氏菌LPS O链的半乳聚糖I和半乳聚糖II的二糖，四糖和六糖的合成及其在抗肺炎克雷伯菌血清筛选中的应用。
• Synthesis of Galα(1,3)Galβ(1,4)GlcNAcα-, Galβ(1,4)GlcNAcα- and GlcNAc-containing neoglycoproteins and their immunological evaluation in the context of Chagas disease
  作者：Nathaniel S Schocker、Susana Portillo、Carlos R N Brito、Alexandre F Marques、Igor C Almeida、Katja Michael

  DOI：10.1093/glycob/cwv081

  日期：——

  The protozoan parasite, Trypanosoma cruzi, the etiologic agent of Chagas disease (ChD), has a cell surface covered by immunogenic glycoconjugates. One of the immunodominant glycotopes, the trisaccharide Galα(1,3)Galβ(1,4)GlcNAcα, is expressed on glycosylphosphatidylinositol-anchored mucins of the infective trypomastigote stage of T. cruzi and triggers high levels of protective anti-α-Gal antibodies (Abs) in infected individuals. Here, we have efficiently synthesized the mercaptopropyl glycoside of that glycotope and conjugated it to maleimide-derivatized bovine serum albumin (BSA). Chemiluminescent-enzyme-linked immunosorbent assay revealed that Galα(1,3)Galβ(1,4)GlcNAcα-BSA is recognized by purified anti-α-Gal Abs from chronic ChD patients ∼230-fold more strongly than by anti-α-Gal Abs from sera of healthy individuals (NHS anti-α-Gal). Similarly, the pooled sera of chronic Chagas disease patients (ChHSP) recognized Galα(1,3)Galβ(1,4)GlcNAcα ∼20-fold more strongly than pooled NHS. In contrast, the underlying disaccharide Galβ(1,4)GlcNAcα and the monosaccharide GlcNAcα or GlcNAcβ conjugated to BSA are poorly or not recognized by purified anti-α-Gal Abs or sera from Chagasic patients or healthy individuals. Our results highlight the importance of the terminal Galα moiety for recognition by Ch anti-α-Gal Abs and the lack of Abs against nonself Galβ(1,4)GlcNAcα and GlcNAcα glycotopes. The substantial difference in binding of Ch vs. NHS anti-α-Gal Abs to Galα(1,3)Galβ(1,4)GlcNAcα-BSA suggests that this neoglycoprotein (NGP) might be suitable for experimental vaccination. To this end, the Galα(1,3)Galβ(1,4)GlcNAcα-BSA NGP was then used to immunize α1,3-galactosyltransferase-knockout mice, which produced antibody titers 40-fold higher as compared with pre-immunization titers. Taken together, our results indicate that the synthetic Galα(1,3)Galβ(1,4)GlcNAcα glycotope coupled to a carrier protein could be a potential diagnostic and vaccine candidate for ChD.

  BSA的差异在于，Ch抗α-Gal抗体与Galα(1,3)Galβ(1,4)GlcNAcα-BSA的结合能力比NHS抗α-Gal抗体强230倍。同样，慢性恰加斯病患者（ChHSP）的混合血清与Galα(1,3)Galβ(1,4)GlcNAcα的结合能力比NHS混合血清强20倍。相比之下，与BSA结合的潜在二糖Galβ(1,4)GlcNAcα和单糖GlcNAcα或GlcNAcβ很少或根本不被纯化的抗α-Gal抗体或恰加斯病患者或健康个体的血清识别。我们的研究结果强调了末端Galα部分对于恰加斯病抗α-Gal抗体识别的重要性，以及缺乏针对非自身Galβ(1,4)GlcNAcα和GlcNAcα糖基化合物的抗体。
• Glycoconjugates and methods for their use
  申请人：Almeida Igor C.

  公开号：US10363319B2

  公开（公告）日：2019-07-30

  Certain embodiments are directed to method for synthesizing and using glycoconjugates on the immunodominant epitope Galα(1,3)Galβ(3(1,4)GlcNAcα (Galα3LNα).

  某些实施方案涉及合成和使用免疫显性表位 Galα(1,3)Galβ(3(1,4)GlcNAcα (Galα3LNα)上的糖结合物的方法。
• GLYCOCONJUGATES AND METHODS FOR THEIR USE
  申请人：ALMEIDA Igor C.

  公开号：US20170333568A1

  公开（公告）日：2017-11-23

  Certain embodiments are directed to method for synthesizing and using glycoconjugates on the immunodominant epitope Galα( 1,3 )Galβ( 3 ( 1,4 )GlcNAcα (Galα 3 LNα).