(3-amido)propyl 3-O-(α-D-galactopyranosyl)-β-D-galactopyranoside | 201667-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3-amido)propyl 3-O-(α-D-galactopyranosyl)-β-D-galactopyranoside
• 英文别名: 3-aminopropyl 3-O-α-D-galactopyranosyl-β-D-galactopyranoside；3-aminopropyl α-D-galactopyranosyl-(1→3)-β-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5S,6R)-2-(3-aminopropoxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 201667-63-2
• 化学式: C₁₅H₂₉NO₁₁
• 分子量: 399.395
• InChiKey: ITVULHHDXBCTPK-PXAZDLICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  205
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (3-amido)propyl 3-O-(α-D-galactopyranosyl)-β-D-galactopyranoside 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  摘要：

  Neoglycoconjugates containing 4, 8, 32, and 64 terminal residues of B-disaccharide (B-DI) or N-acetylneuraminic acid (Neu5Ac) attached to poly(aminoamide)-type dendrimers (PAMAMs) were synthesized. The ability of B-DI conjugates to bind natural xenoantibodies (anti-B-DI, antibodies) and the ability of Neu5Ac conjugates to inhibit the hemagglutinin-mediated adhesion of influenza virus were studied. The biological activity of PAMAM conjugates turned out to be higher than that of free carbohydrate ligands, but less than that of multivalent glycoconjugates based on other types of synthetic polymeric carriers. A conformational analysis of PAMAM matrices and resulting conjugates was performed to determine the statistical distances between carbohydrate ligands. The computations revealed the tendency of the PAMAM chains toward compaction and formation of dense globules. The process results in a decrease in the distances between the carbohydrate ligands in the conjugates and, hence, could affect the ability of glycoconjugates to efficiently bind the polyvalent carbohydrate-recognizing proteins.

  DOI：

  10.1023/a:1021293532046
• 作为产物：
  描述：

  allyl β-D-galactopyranoside 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 硫酸 、 氢气 、 四正辛基溴化铵 、 三乙胺 、 9-硼双环[3.3.1]壬烷 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -10.0~60.0 ℃ 、202.65 kPa 条件下， 反应 346.5h， 生成 (3-amido)propyl 3-O-(α-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  A novel synthesis of α-d-Galp-(1→3)-β-d-Galp-1-O-(CH2)3NH2, its linkage to activated matrices and absorption of anti-αGal xenoantibodies by affinity columns

  摘要：

  Pig organs transplanted into primates are rapidly rejected because of the interaction between Ga1 alpha(1-->3)Ga1 epitopes carried by the graft and natural antibodies (anti-alpha Ga1 antibodies) present in the blood of the recipient. This report describes a simplified synthesis of the xenogeneic disaccharide and its linkage to activated gel matrices. The digalactosides alpha-D-Ga1p-(1-->3)-alpha,beta-D-Ga1p-OAll were synthesized by the condensation of the trichloroacetimidoyl 2,3,4,6-tetra-O-benzyl-beta-D-galactopyranoside donor with the 3,4-unprotected allyl 2,6-di-O-benzyl-alpha- or beta-D-galactopyranoside acceptor precursor. Deallylation and hydrogenolysis led to the free digalactoside, whereas hydrogenolysis alone resulted in the 1-O-propyl digalactoside. Both products were tested by inhibition ELISA of natural anti-Ga1 alpha(1-->3)Ga1 antibodies. The alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OPr was found to be the best inhibitor. Thus, the allyl group of the partially benzylated alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OAll was engineered, via the hydroxy-, the tosyloxy- and the azidopropyl intermediates, into an aminopropyl group amenable to binding to N-hydroxysuccinimide-activated agarose gel matrices in order to obtain specific immunoabsorption columns. Columns made of gel substituted with 5 mu mol of disaccharide per milliliter were found efficient for the immunoabsorption of anti-alpha Ga1 antibodies from human plasma. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00010-0

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。
• High affinity adaptor molecules for redirecting antibody specifity
  申请人：Collinson Albert

  公开号：US09284548B2

  公开（公告）日：2016-03-15

  Disclosed are methods for identifying high affinity adaptor molecules that bind to both a circulating antibody and a target molecule and redirect the specificity of the circulating antibody to the target molecule. Exemplary high affinity adaptor molecules are also provided.

  本发明涉及识别高亲和力的适配分子的方法，这些适配分子能够与循环抗体和目标分子结合，并将循环抗体的特异性重定向到目标分子。同时还提供了具有代表性的高亲和力适配分子。
• A novel synthesis of α-d-Galp-(1→3)-β-d-Galp-1-O-(CH2)3NH2, its linkage to activated matrices and absorption of anti-αGal xenoantibodies by affinity columns
  作者：Jérôme Liaigre、Didier Dubreuil、Jean-Paul Pradère、Jean-François Bouhours

  DOI：10.1016/s0008-6215(00)00010-0

  日期：2000.5

  Pig organs transplanted into primates are rapidly rejected because of the interaction between Ga1 alpha(1-->3)Ga1 epitopes carried by the graft and natural antibodies (anti-alpha Ga1 antibodies) present in the blood of the recipient. This report describes a simplified synthesis of the xenogeneic disaccharide and its linkage to activated gel matrices. The digalactosides alpha-D-Ga1p-(1-->3)-alpha,beta-D-Ga1p-OAll were synthesized by the condensation of the trichloroacetimidoyl 2,3,4,6-tetra-O-benzyl-beta-D-galactopyranoside donor with the 3,4-unprotected allyl 2,6-di-O-benzyl-alpha- or beta-D-galactopyranoside acceptor precursor. Deallylation and hydrogenolysis led to the free digalactoside, whereas hydrogenolysis alone resulted in the 1-O-propyl digalactoside. Both products were tested by inhibition ELISA of natural anti-Ga1 alpha(1-->3)Ga1 antibodies. The alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OPr was found to be the best inhibitor. Thus, the allyl group of the partially benzylated alpha-D-Ga1p-(1-->3)-beta-D-Ga1p-OAll was engineered, via the hydroxy-, the tosyloxy- and the azidopropyl intermediates, into an aminopropyl group amenable to binding to N-hydroxysuccinimide-activated agarose gel matrices in order to obtain specific immunoabsorption columns. Columns made of gel substituted with 5 mu mol of disaccharide per milliliter were found efficient for the immunoabsorption of anti-alpha Ga1 antibodies from human plasma. (C) 2000 Elsevier Science Ltd. All rights reserved.
• ——
  作者：D. E. Tsvetkov、P. E. Cheshev、A. B. Tuzikov、A. A. Chinarev、G. V. Pazynina、M. A. Sablina、A. S. Gambaryan、N. V. Bovin、R. Rieben、A. S. Shashkov、N. E. Nifant'ev

  DOI：10.1023/a:1021293532046

  日期：——

  Neoglycoconjugates containing 4, 8, 32, and 64 terminal residues of B-disaccharide (B-DI) or N-acetylneuraminic acid (Neu5Ac) attached to poly(aminoamide)-type dendrimers (PAMAMs) were synthesized. The ability of B-DI conjugates to bind natural xenoantibodies (anti-B-DI, antibodies) and the ability of Neu5Ac conjugates to inhibit the hemagglutinin-mediated adhesion of influenza virus were studied. The biological activity of PAMAM conjugates turned out to be higher than that of free carbohydrate ligands, but less than that of multivalent glycoconjugates based on other types of synthetic polymeric carriers. A conformational analysis of PAMAM matrices and resulting conjugates was performed to determine the statistical distances between carbohydrate ligands. The computations revealed the tendency of the PAMAM chains toward compaction and formation of dense globules. The process results in a decrease in the distances between the carbohydrate ligands in the conjugates and, hence, could affect the ability of glycoconjugates to efficiently bind the polyvalent carbohydrate-recognizing proteins.