O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine | 133477-83-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine
• 英文别名: peracetylated N-acetyl-D-galactosamine α-O-L-threonine；(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-2-aminobutanoic acid
• CAS: 133477-83-5
• 化学式: C₁₈H₂₈N₂O₁₁
• 分子量: 448.427
• InChiKey: FKLRVDCXGWJCEC-IDCTWFJGSA-N

物化性质

• 沸点：
  647.9±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  190
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以0.05 g的产率得到2-(acetylamino)-2-deoxy-α-D-galactopyranosyl-L-threonine
  参考文献：
  名称：

  Synthesis of a Single-Molecule l-Rhamnose-Containing Three-Component Vaccine and Evaluation of Antigenicity in the Presence of Anti-l-Rhamnose Antibodies

  摘要：

  Carbohydrates are generally considered to be poorly immunogenic. Therefore, new approaches for enhancing their immunogenicity are important for the development of carbohydrates as vaccine components. We hypothesized that conjugation of an L-rhamnose (Rha) moiety to a carbohydrate antigen would enhance the antigenicity of the antigen in mice possessing anti-Rha antibodies via an antibody-dependent antigen uptake mechanism. To explore this hypothesis, we synthesized a single-molecule three-component vaccine containing the GalNAc-O-Thr (Tn) tumor-specific antigen, a 20 amino acid helper T-cell epitope (YAF) derived from an outer-membrane protein of Neisseria meningitides, and a Rha moiety. The vaccine was synthesized by automated Fmoc-based solid-phase peptide synthesis and deacetylated by brief treatment with NaOMe. Groups of female BALB/c mice were immunized and boosted with Rha-ovalbumin (Rha-OVA) formulated with either TiterMax Gold or Sigma Adjuvant System for a period of 35 days in order to determine optimal conditions for generating anti-Rha titers in mice. Anti-Rha antibody titers were > 100 fold higher in groups of mice immunized with Rha-OVA than in the control groups. Mice producing anti-Rha were challenged with Rha-YAF-Tn or YAF-Tn. Sera collected from the groups initially immunized with Rha-OVA and later challenged with Rha-YAF-Tn showed a 2-fold increase in anti-Tn titer at 1/100 serum dilution relative to mice not immunized with Rha-OVA. An in vitro T-cell proliferation study using cells primed with either Rha-YAF-Tn or YAF-Tn was done to examine possible differences in antigen uptake and presentation due to anti-Rha antibody and chemical modification. Proliferation of T cells was stimulated by a 10-fold lower antigen concentration in the presence of Rha antibodies. The results strongly suggest that T cells present in the spleen were presented with higher concentrations of Rha-YAF-Tn as a result of the presence of the anti-Rha antibodies.

  DOI：

  10.1021/ja107029z
• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 在 铜 、 锌 哌啶 、 吡啶 、 乙醚 、 三氟甲磺酸三甲基硅酯 、 triflic azide 、 乙酸肼 、 potassium carbonate 、 copper(II) sulfate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine
  参考文献：
  名称：

  Xu, Ran; Hanson, Sarah R.; Zhang, Zhiwen, Journal of the American Chemical Society, 2004, vol. 126, # 48, p. 15654 - 15655

  摘要：

  DOI：

文献信息

• A Novel and Efficient Route towards α-GalNAc-Ser and α-GalNAc-Thr Building Blocks for Glycopeptide Synthesis
  作者：Gottfried A. Winterfeld、Yukishige Ito、Tomoya Ogawa、Richard R. Schmidt

  DOI：10.1002/(sici)1099-0690(199905)1999:5<1167::aid-ejoc1167>3.0.co;2-2

  日期：1999.5
• α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi
  作者：Maristela B. Martins-Teixeira、Vanessa L. Campo、Monica Biondo、Renata Sesti-Costa、Zumira A. Carneiro、João S. Silva、Ivone Carvalho

  DOI：10.1016/j.bmc.2013.01.027

  日期：2013.4

  This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(alpha GalNAc)Ser] 3 and cyclo[Asp-(alpha GalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids alpha GalNAc-Ser 7 or alpha GalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by a-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with alpha GalN(3)Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 mu M), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%). (C) 2013 Elsevier Ltd. All rights reserved.
• Nitroglycal Concatenation: A Broadly Applicable and Efficient Approach to the Synthesis of Complex O-Glycans
  作者：Gottfried A. Winterfeld、Richard R. Schmidt

  DOI：10.1002/1521-3773(20010716)40:14<2654::aid-anie2654>3.0.co;2-l

  日期：2001.7.16

  Base-catalyzed glycosylations provide the basis for a new and general entry to the synthesis of mucin-type O-glycans. The desired α-linked 2-acetamidoglycosyl amino acids B are accessible selectively starting from glycals of type A. Fmoc=9-fluorenylmethoxycarbonyl.