2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-<(R)-1-carboxyethyl>-2-deoxy-D-glucopyranose | 4500-70-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-<(R)-1-carboxyethyl>-2-deoxy-D-glucopyranose
• 英文别名: 2-acetamido-4-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-3-O-[(R)-1-carboxy-ethyl]-2-deoxy-α-d-glucopyranose；N-acetyl-β-D-glucosaminyl-(1->4)-N-acetylmuramic acid；N-GlcNAc-β-(1,4)-N-MurNAc；2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-((R)-1-carboxyethyl)-2-deoxy-D-glucopyranose；N-Acetyl-D-glucosaminyl-(1-4)-N-acetylmuramic Acid；(2R)-2-[(3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoic acid
• CAS: 4500-70-3；13100-83-9；20223-57-8；20314-08-3；64199-63-9；105662-91-7
• 化学式: C₁₉H₃₂N₂O₁₃
• 分子量: 496.469
• InChiKey: WQKIVDUWFNRJHE-NNRGKNABSA-N

物化性质

• 沸点：
  948.9±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  234
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-[(R)-1-(methoxycarbonyl)ethyl]-α-D-glucopyranoside 在 三乙基硅烷 、 碘 、 sodium methylate 、 silver trifluoromethanesulfonate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 54.25h， 生成 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3-O-<(R)-1-carboxyethyl>-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  [EN] CRYSTAL STRUCTURE OF STAPHYLOCOCCUS AUREUS AUTOLYSIN E, METHOD OF PRODUCING THE CRYSTAL AND ITS USE IN SCREENING METHODS
  [FR] STRUCTURE CRISTALLINE D'AUTOLYSINE E DE STAPHYLOCOCCUS AUREUS, PROCÉDÉ DE PRODUCTION DU CRISTAL ET SON UTILISATION DANS LES PROCÉDÉS DE CRIBLAGE

  摘要：

  这项发明涉及测定和评估金黄色葡萄球菌（S. aureus）的自溶素E（AtlE）的晶体结构，或AtlE的结晶片段，制备AtlE晶体的方法以及相应的结晶试剂盒，以及其在筛选AtlE的N-乙酰葡萄糖苷酶活性抑制剂的方法中的应用，用于获得原子空间关系数据，并用于识别AtlE的结合化合物，例如通过计算筛选。

  公开号：

  WO2016173603A1

文献信息

• A convenient synthetic route to the disaccharide repeating-unit of peptidoglycan
  作者：Darko Kantoci、Dina Keglević、Andrew E. Derome

  DOI：10.1016/0008-6215(87)80218-5

  日期：1987.5

  methyl ester group, gave benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D- glucopyranosyl)-6-O-benzyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-alpha-D- glucopyranoside. An alternative route for the preparation of 2 is described.

  易于获得的苄基2-乙酰氨基-6-O-苄基-2-脱氧-3-O-[（R）-1-（甲氧羰基）乙基]-α-D-吡喃葡萄糖苷与3,4,6-tri的糖基化-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基氯（2），在不存在碱的情况下，使用三氟甲磺酸银法，得到65-70％的完全保护的[β-D-GlcNPhth -（1 ---- 4）-MurNAc]甲酯衍生物4，其结构基于500-MHz 1H-nmr数据确定。2,2'-Dideoxy-2,2'-diphthalimido-beta，β-海藻糖六乙酸盐是副产物。从4除去Phth基团，然后进行乙酰化，得到90％的乙酰化1,6-二-O-苄基衍生物5，在进行皂化和催化氢化后，得到2-acetamido-4-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡糖基）-3-O-[（R-1--1-羧乙基）-2-脱氧-D-吡喃葡糖。同样，5被转化为乙酰化的甲酯衍
• Novel mannosyl derivatives of peptidoglycan monomer: Synthesis and biological evaluation of immunomodulatory properties
  作者：Rosana Ribić、Lidija Habjanec、Marija Brgles、Srđanka Tomić、Jelka Tomašić

  DOI：10.1016/j.bmc.2009.06.016

  日期：2009.8

  The aim of this work was to prepare mannosyl derivatives of peptidoglycan monomer (PGM, beta-D-GlcNAc( 1 -> 4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(epsilon NH(2))-D-Ala-D-Ala) in order to study the effects of mannosylation on adjuvant (immunostimulating) activity. Novel Man-OCH(2)CH(CH(3))CO-PGM isomers were substrates for N-acetylmuramyl-L-alanine amidase, like the parent PGM molecule. Adjuvant activity of Man-OCH(2)CH(CH(3)) CO-PGM was tested in the mouse model using ovalbumin as an antigen. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of novel adamantylacetyl derivative of peptidoglycan monomer—biological evaluation of immunomodulatory peptidoglycan monomer and respective derivatives with lipophilic substituents on amino group
  作者：Đurđica Ljevaković、Jelka Tomašić、Vesna Šporec、Beata Halassy Špoljar、Ivana Hanzl-Dujmović

  DOI：10.1016/s0968-0896(00)00172-3

  日期：2000.10

  Novel synthetic analogue of immunomodulatory peptidoglycan monomer 1 (PGM), (adamant-1-yl)-CH(2)CO-PGM (2), was prepared by acylation of epsilon-amino group of diaminopimelic acid with symmetrical (adamant-1-yl)-acetic acid anhydride in the presence of triethylamine. The product was isolated by gel filtration on Sephadex G-25, followed by ion exchange chromatography on SP-Sephadex C-25. The susceptibility of (adamant-l-yi)-CH2CO-PGM to hydrolysis with N-acetylmuramyl-L-alanine amidase was demonstrated, and the product of hydrolysis, (adamant-1-yl)-CH(2)CO-pentapeptide 3, was characterized. Both 2 and 3 are water soluble and non-pyrogenic compounds. Immunomodulatory activity of PGM (adamant-1-yl)-CH(2)CO-PGM and structurally related derivative Boc-Tyr-PGM was compared in experiments in vivo, in mice, using ovalbumin (OVA) as an antigen. All three tested compounds exhibited comparable immunostimulating effects with respect to the induction of anti-ovalbumin immunoglobulin G. The results of evaluation of biological activity show that the substitution of free amino group in the parent peptidoglycan molecule with bulky lipophilic substituents did not affect the susceptibility to hydrolysis with N-acetylmuramyl-L-alanine amidase and did not alter markedly the immunostimulating activity. The results also indicate that the free amino group in the peptide chain is not a necessary requirement in the mechanism of immunostimulation of tested immunomodulators. (C) 2000 Elsevier Science Ltd. All rights reserved.