2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose | 104430-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose
• 英文别名: (R)-2-(((1R,2S,3R,4R,5R)-4-acetamido-2-(benzyloxy)-6,8-dioxabicyclo[3.2.1]octan-3-yl)oxy)propanoic acid；2-acetamido-1,6-anhydro-4-O-benzyl-2-deoxy-3-O-[(1R)-1-carboxyethyl]-β-D-glucopyranose；2-acetylamino-1,6-anhydro-2-deoxy-4-O-benzyl-3-O-[(1R)-1-(carboxyl)ethyl]-β-D-glucopyranose；(2R)-2-[[(1R,2S,3R,4R,5R)-4-acetamido-2-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy]propanoic acid
• CAS: 104430-65-1
• 化学式: C₁₈H₂₃NO₇
• 分子量: 365.383
• InChiKey: FMBNZACFIBXRDQ-VRBXCPMESA-N

物化性质

• 沸点：
  623.9±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  103.32
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose 在 palladium on activated charcoal N-羟基丁二酰亚胺 、 氢气 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 为溶剂， -10.0~20.0 ℃ 、3.5 MPa 条件下， 反应 23.25h， 生成 2-Acetamido-1,6-anhydro-β-muramoyl-L-alanyl-D-isoglutamin
  参考文献：
  名称：

  寡糖的构建基块，LXIX。1,6-脱水村寨肽的合成

  摘要：

  给出了1，6-脱水-β-山梨酸8的有效合成。通过三氟甲磺酸银和活化的分子，与作为糖基供体的3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖基溴化物（12）偶联至二糖13的收率非常好筛（10Å）。二糖15与二肽9的肽偶联导致16，从中得到1,6-脱水村酰胺基肽β-D-GlcNAc-（1 4）-1,6-脱水-β-MurNAc-L-Ala-D可以得到-异-GlnOH（17）。

  DOI：

  10.1002/jlac.198619860408
• 作为产物：
  描述：

  2-Acetamido-1,6-anhydro-4-O-benzyl-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.5h， 以950 mg的产率得到2-Acetamido-1,6-anhydro-4-O-benzyl-3,O-<(1R)-1-carboxyethyl>-2-desoxy-β-D-glucopyranose
  参考文献：
  名称：

  寡糖的构建基块，LXIX。1,6-脱水村寨肽的合成

  摘要：

  给出了1，6-脱水-β-山梨酸8的有效合成。通过三氟甲磺酸银和活化的分子，与作为糖基供体的3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖基溴化物（12）偶联至二糖13的收率非常好筛（10Å）。二糖15与二肽9的肽偶联导致16，从中得到1,6-脱水村酰胺基肽β-D-GlcNAc-（1 4）-1,6-脱水-β-MurNAc-L-Ala-D可以得到-异-GlnOH（17）。

  DOI：

  10.1002/jlac.198619860408

文献信息

• Synthesis of Diaminopimelic Acid Containing Peptidoglycan Fragments and Tracheal Cytotoxin (TCT) and Investigation of Their Biological Functions
  作者：Akiko Kawasaki、Yukie Karasudani、Yuji Otsuka、Mizuho Hasegawa、Naohiro Inohara、Yukari Fujimoto、Koichi Fukase

  DOI：10.1002/chem.200801121

  日期：2008.11.17

  a new synthetic method for an orthogonally protected meso-DAP derivative, and then we constructed the glycopeptide structures. The ability of these fragments to stimulate human Nod1, as well as differences in Nod1 recognition of the variety of synthesized ligand structures were examined. The results showed that the substitution of the N terminus of iE-DAP is necessary for stronger Nod1 recognition

  细菌细胞壁肽聚糖（PGN）是有效的免疫刺激剂和免疫佐剂。革兰氏阴性细菌和某些革兰氏阳性细菌的PGN包含中二氨基庚二酸（meso-DAP），最近我们已经证明细胞内蛋白Nod1是PGN受体，可以识别含DAP的肽。在这项研究中，我们实现了含DAP的PGN片段的合成，包括气管细胞毒素（TCT），GlcNAc-（β1-4）-（脱水）MurNAc-L-Ala-γ-D-Glu-的第一化学合成。 meso-DAP-D-Ala和DAP型PGN的重复单元GlcNAc-β1-4-MurNAc-L-Ala-γ-D-Glu-meso-DAP-D-Ala。对于PGN片段的合成，我们首先为正交保护的meso-DAP衍生物建立了一种新的合成方法，然后构建了糖肽结构。检查了这些片段刺激人Nod1的能力，以及Nod1对各种合成配体结构的识别的差异。结果表明，为了增强Nod1的识别能力，必须对iE-DAP的N末端进行取代，但是
• WO2020109792A5
  申请人：——

  公开号：WO2020109792A5

  公开（公告）日：2022-11-09
• Hesek, Dusan; Lee, Mijoon; Zhang, Weilie, Journal of the American Chemical Society, 2009, vol. 131, p. 5187 - 5193
  作者：Hesek, Dusan、Lee, Mijoon、Zhang, Weilie、Noll, Bruce C.、Mobashery, Shahriar

  DOI：——

  日期：——
• Bacterial AmpD at the Crossroads of Peptidoglycan Recycling and Manifestation of Antibiotic Resistance
  作者：Mijoon Lee、Weilie Zhang、Dusan Hesek、Bruce C. Noll、Bill Boggess、Shahriar Mobashery

  DOI：10.1021/ja9025566

  日期：2009.7.1

  The bacterial, enzyme AmpD is an early catalyst in commitment of cell wall metabolites to the recycling events within the cytoplasm. The key internalized metabolite of Cell watt recycling, beta-D-N-acetytgtucosamine-(1 -> 4)-1,6-anhydro-beta-N-acetytmuramyl-L-Ala-gamma-D-Glu-meso-DAP-D-Ala-D-Ala (compound 1), is a poor substrate for AmpD. Two additional metabolites, 1,6-anhydro-N-acetyimuramyl-peptidyl derivatives 2a and 2c, served as substrates for AmpD with a k(cat)/K-m of >10(4) M-1 s(-1). The enzyme hydrolytically processes the lactyl amide bond of the 1,6-anhydro-N-acetylmuramyl moiety. The syntheses of these substrates and other ligands are reported herein, which made the characterization of the enzymic reaction possible. Furthermore, it is documented that the enzyme is specific for both the atypical peptide stem of the cell wall fragments and the presence of the sterically encumbered 1,6-anhydro-N-acetylmuramyl moiety; hence it is a peptidase with a unique function in bacterial. physiology. The implications of the function of this catalyst for the entry into the cell wall recycling events and the reversal of induction of the production of beta-lactamase, an antibiotic resistance determinant, are discussed.
• 1,6-AnhMurNAc derivatives for assay development of amidase AmiD
  作者：Frédéric Mercier、Astrid Zervosen、Nathalie Teller、Jean-Marie Frère、Raphaël Herman、Anne Pennartz、Bernard Joris、André Luxen

  DOI：10.1016/j.bmc.2010.09.010

  日期：2010.11

  Various peptidoglycan fragments were synthesized from two anhydro-muramic acid derivatives protected with a Bn or a PMB group at the 4th position, in homogenate phase or on a solid support. In order to facilitate HPLC detection, a chromophoric group was attached to the peptide chain. The periplasmic amidase sAmiD of Escherichia coli was used to cleave the amide bond between the lactyl group of the MurNAc and the alpha-amino group of L-Ala where the peptide chain was at least a dipeptide (L-Ala-gamma-D-Glu) amidated by benzylamine on the c-carboxyl group of D-Glu. In the presence of a tripeptide chain (L-Ala-gamma-D-Glu-L-Lys) or a tetrapeptide chain (L-Ala-gamma-D-Glu-m-A(2)pm-D-Ala) higher hydrolysis rates were observed. We have also demonstrated that the presence of TNB on the epsilon-amino group of L-Lys only has a small influence on the hydrolysis capacity of sAmiD. (C) 2010 Elsevier Ltd. All rights reserved.