1-N-(6-aminohexanoyl)-β-D-galactopyranosylamine | 38822-56-9

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-N-(6-aminohexanoyl)-β-D-galactopyranosylamine
• 英文别名: N-(ε-aminocaproyl)-β-D-galactopyranosylamine；6-Amino-N-beta-D-galactopyranosyl hexanamide；6-amino-N-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]hexanamide
• CAS: 38822-56-9
• 化学式: C₁₂H₂₄N₂O₆
• 分子量: 292.332
• InChiKey: FJNVLTLMGXYGGP-NBIDRCSRSA-N

物化性质

• 熔点：
  206-208°C
• 溶解度：
  可溶于DMSO（轻微加热）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  145
• 氢给体数：
  6
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  29329990

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基-3-环丁烯-1,2-二酮 、 1-N-(6-aminohexanoyl)-β-D-galactopyranosylamine 以 甲醇 为溶剂， 以64.5%的产率得到N-(N'-(2-methoxy-3,4-dioxa-1-cyclobuten-1-yl)--aminocaproyl)--D-galactopyranosylamine
  参考文献：
  名称：

  基于模块化结构设计的大肠杆菌耐热肠毒素的高亲和力五价配体

  摘要：

  DOI：

  10.1021/ja993388a
• 作为产物：
  描述：

  1N-(tert-butoxycarbonyl-6-aminohexanoyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylamine 在 sodium hydroxide 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 1-N-(6-aminohexanoyl)-β-D-galactopyranosylamine
  参考文献：
  名称：

  Synthesis and characterisation of poly (l-lactic acid) galactosyl derivatives; access to functionalised microspheres

  摘要：

  A new series of galactosyl-derived polymers has been used for the preparation of microspheres, The strategy is based on the modification of the terminal carboxylic group L-PLA (73.000) by coupling to a galactosyl antenna in the presence of the peptide coupling agents: DCC/HOBT. The degree of functionalisation varies between 60 and 70%, and antenna density between 1.74 and 2,78, The characterisations of the new products were carried out using H-1 NMR, gel permeation chromatography, and acid base titration; the size of the functionalised microspheres was determined to be 210-270 mu m by DLS. (C) 2000 Published by Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02216-9

文献信息

• Solution and Crystallographic Studies of Branched Multivalent Ligands that Inhibit the Receptor-Binding of Cholera Toxin
  作者：Zhongsheng Zhang、Ethan A. Merritt、Misol Ahn、Claudia Roach、Zheng Hou、Christophe L. M. J. Verlinde、Wim G. J. Hol、Erkang Fan

  DOI：10.1021/ja027584k

  日期：2002.11.1

  The structure-based design of multivalent ligands offers an attractive strategy toward high affinity protein inhibitors. The spatial arrangement of the receptor-binding sites of cholera toxin, the causative agent of the severe diarrheal disease cholera and a member of the AB(5) bacterial toxin family, provides the opportunity of designing branched multivalent ligands with 5-fold symmetry. Our modular synthesis enabled the construction of a family of complex ligands with five flexible arms each ending with a bivalent ligand. The largest of these ligands has a molecular weight of 10.6 kDa. These ligands are capable of simultaneously binding to two toxin B pentamer molecules with high affinity, thus blocking the receptor-binding process of cholera toxin. A more than million-fold improvement over the monovalent ligand in inhibitory power was achieved with the best branched decavalent ligand. This is better than the improvement observed earlier for the corresponding nonbranched pentavalent ligand. Dynamic light scattering studies demonstrate the formation of concentration-dependent unique 1:1 and 1:2 ligand/toxin complexes in solution with no sign of nonspecific aggregation. This is in complete agreement with a crystal structure of the branched multivalent ligand/toxin B pentamer complex solved at 1.45 Angstrom resolution that shows the specific 1:2 ligand/toxin complex formation in the solid state. These results reiterate the power of the structure-based design of multivalent protein ligands as a general strategy for achieving high affinity and potent inhibition.
• [EN] HUMAN SERUM LECTIN - INDUCED APOPTOSIS AND METHOD FOR DETECTING APOPTOSIS<br/>[FR] APOPTOSE INDUITE PAR DES LECTINES DE SERUM HUMAIN ET PROCEDE DE DETECTION D'APOPTOSE
  申请人：——

  公开号：WO1997031107A2

  公开（公告）日：1997-08-28

  [EN] The unifying theme of the present invention is the description of a class of proteins present in human blood which have the capacity to selectively recognize and induce apoptosis of cells which convey abnormal surface carbohydrates. Alterations in cellular glycosylation can result from either species-specific differences or may reflect cancer-associated changes. Human serum carbohydrate binding proteins, referred to as lectins, were isolated on several different carbohydrate columns including Gal alpha (papGal), GalNAc, GlcNAc, Fucose, Mannose and Melibiose. These lectins were shown to cause apoptosis of porcine aortic endothelial cells. This demonstrates a new pathway leading to endothelial cell death following xenogenic stress that may be important in the pathogenesis of xenograft rejection and suggests new therapeutic approaches to the treatment of xenograft rejection. Further, these mammalian carbohydrate binding proteins are herein shown to cause apoptosis of breast cancer and lung cancer cells in vitro, and can be used as a cytotoxic agent against human tumour cells. Significantly, the proteins of the present invention exhibit minimal binding or reactivity against normally glycosylated human cells. This invention also relates to a novel bioassay for the detection and quantitation of cellular apoptosis in vitro, and to the utility of this assay for the identification and evaluation of compounds with potential apogenic activity.
  [FR] Le thème directeur de la présente invention est la description d'une classe de protéines présentes dans le sang humain, lesquelles ont la capacité de reconnaître et d'induire sélectivement l'apoptose de cellules portant des glucides de surface anormaux. Des modifications de la glycosilation cellulaire peuvent résulter de différences spécifiques d'espèces ou peuvent refléter des changements associés à un cancer. On a isolé des protéines liant un glucide de sérum humain, appelées lectines, sur différentes colonnes de glucide, notamment Gal alpha (papGal), GalNAc, GlcNAc, fucose, mannose et mélibiose. On a démontré que ces lectines provoquent l'apoptose de cellules endothéliales aortiques porcines. Ceci démontre une nouvelle voie conduisant à la mort de cellules endothéliales après un stress xénogène pouvant être important dans la pathogénèse du rejet d'hétérogreffes et suggère de nouvelles approches thérapeutiques dans le traitement du rejet d'hétérogreffes. De plus, ces protéines de liaison de glucides mammifères sont ici présentées comme étant la cause de l'apoptose de cellules in vitro du cancer du sein et du cancer des poumons et elles peuvent être utilisées en tant qu'agent cytotoxique contre des cellules tumorales humaines. De manière significative, les protéines de la présente invention présentent une liaison ou une réactivité minimale contre des cellules humaines glycosilées de façon normale. Cette invention concerne également un nouveau dosage biologique de détection et de quantification de l'apoptose cellulaire in vitro, ainsi que l'utilité de ce dosage pour l'identification et l'évaluation de composés présentant une activité apogénique potentielle.