allyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside | 399036-05-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,5-dibenzoyloxy-4-hydroxy-6-prop-2-enoxyoxan-2-yl]methyl benzoate
• CAS: 399036-05-6
• 化学式: C₃₀H₂₈O₉
• 分子量: 532.547
• InChiKey: JFZMRICZAZNYQD-OFBRLNSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 sodium azide 、 18-冠醚-6 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 135.67h， 生成
  参考文献：
  名称：

  Study of glycosylation with N-trichloroacetyl-d-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues

  摘要：

  The syntheses of 2-aminoethyl glycosides of the pentasaccharides Neu5Ac-alpha (2 --> 3)-Gal-beta (3(1 --> 4)-GlcNAc-beta (3(1 --> 3)-Gal-beta (1 --> 4)-Glc and Neu5Ac-alpha (2 --> 3)-Gal-beta (1 --> 3)-GlcNAc-beta (1 --> 3)-Gal-beta (1 --> 4)-Glc, their asialo di-, tri-, and tetrasaccharide fragments, and analogues included a systematic study of glycosylation with variously protected mono- and disaccharide donors derived from N-trichloroacetyl-D-glucosamine of galactose, lactose, and lactosamine glycosyl acceptors bearing benzoyl protection around the OH group to be glycosylated. Despite the. low reactivity of these acceptors, stereo specificity and good to excellent yields were obtained with NIS-TfOH-activated thioglycoside donors of such type, or with AgOTf-activated glycosyl bromides, while other promotors, as well as a trichloroacetimidate donor, were less effective, and a beta -acetate donor was inactive. In NIS-TfOH-promoted glycosylation with the thioglycosides, the use of TfOH in catalytic amount led to rapid formation of the corresponding oxazoline, but the quantity of TfOH necessary for further efficient coupling with an acceptor depended on the reactivity of the donor, varying from 0.07 equiv for a 3,6-di-O-benzylated monosaccharide derivative to 2.1 equiv for a peracetylated disaccharide one. In the glycosylation products, the N-trichloroacetyl group was easily converted into N-acetyl by alkaline hydrolysis followed by N-acetylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00213-0
• 作为产物：
  描述：

  allyl β-D-galactopyranoside 在 吡啶 、 二正丁基氧化锡 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 35.5h， 生成 allyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1093/glycob/cwv081

文献信息

• 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。
• Sialylation with systematically protected allyl galactoside acceptors using sialyl phosphate donors
  作者：Kenta Kurimoto、Hatsuo Yamamura、Atsushi Miyagawa

  DOI：10.1016/j.tetlet.2016.02.052

  日期：2016.3

  Various N-protected sialyl donors were synthesized and utilized in sialylation to investigate the reactivity and stereoselectivity of sialyl phosphate donors. Furthermore, in order to understand the effects of protecting groups and hydroxyl group positions on galactosyl acceptors, the sialylation efficiencies of all of the hydroxy groups on galactoses, which were protected with benzyl or benzoyl groups, were investigated. Consequently, the sialylation of N-acetyl-5-N,4-O-oxazolidinone-protected sialyl phosphate donors with allyl galactosides was accomplished and gave the GM4 regioisomers. (C) 2016 Elsevier Ltd. All rights reserved.
• 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).
• Study of glycosylation with N-trichloroacetyl-d-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues
  作者：Andrei A. Sherman、Olga N. Yudina、Yury V. Mironov、Elena V. Sukhova、Alexander S. Shashkov、Vladimir M. Menshov、Nikolay E. Nifantiev

  DOI：10.1016/s0008-6215(01)00213-0

  日期：2001.11

  The syntheses of 2-aminoethyl glycosides of the pentasaccharides Neu5Ac-alpha (2 --> 3)-Gal-beta (3(1 --> 4)-GlcNAc-beta (3(1 --> 3)-Gal-beta (1 --> 4)-Glc and Neu5Ac-alpha (2 --> 3)-Gal-beta (1 --> 3)-GlcNAc-beta (1 --> 3)-Gal-beta (1 --> 4)-Glc, their asialo di-, tri-, and tetrasaccharide fragments, and analogues included a systematic study of glycosylation with variously protected mono- and disaccharide donors derived from N-trichloroacetyl-D-glucosamine of galactose, lactose, and lactosamine glycosyl acceptors bearing benzoyl protection around the OH group to be glycosylated. Despite the. low reactivity of these acceptors, stereo specificity and good to excellent yields were obtained with NIS-TfOH-activated thioglycoside donors of such type, or with AgOTf-activated glycosyl bromides, while other promotors, as well as a trichloroacetimidate donor, were less effective, and a beta -acetate donor was inactive. In NIS-TfOH-promoted glycosylation with the thioglycosides, the use of TfOH in catalytic amount led to rapid formation of the corresponding oxazoline, but the quantity of TfOH necessary for further efficient coupling with an acceptor depended on the reactivity of the donor, varying from 0.07 equiv for a 3,6-di-O-benzylated monosaccharide derivative to 2.1 equiv for a peracetylated disaccharide one. In the glycosylation products, the N-trichloroacetyl group was easily converted into N-acetyl by alkaline hydrolysis followed by N-acetylation. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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。