2-Acetamido-1,6-anhydro-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose | 42321-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 2-Acetamido-1,6-anhydro-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose
• 英文别名: 1,6-anhydro-N-acetylmuramic acid methyl ester；2-acetamido-1,6-anhydro-4-O-benzyl-2-deoxy-3-O-[(1R)-1-(methoxycarbonyl)ethyl]-β-D-glucopyranose；2-Acetamido-1,6-anhydro-4-O-benzyl-2-deoxy-3-O-[(1R)-1-(methoxycarbonyl)ethyl]-beta-D-glucopyranose；methyl (2R)-2-[[(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy]propanoate
• CAS: 42321-03-9
• 化学式: C₁₂H₁₉NO₇
• 分子量: 289.285
• InChiKey: ZZDQFKCVVBKWNU-PKKPQKKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Acetamido-1,6-anhydro-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 为溶剂， 反应 0.5h， 以460 mg的产率得到1,6-anhydro-N-acetylmuramic acid
  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：

  在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 2-Acetamido-1,6-anhydro-2-desoxy-3-O-<(1R)-1-(methoxycarbonyl)ethyl>-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Muramyl Peptides Containing meso-Diaminopimelic Acid

  摘要：

  Chain-extension Of L-glutamate aldehyde 3 by means of the Wittig-Homer reaction furnished the desired C-7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D-isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanylL-isoglutaminyl-(2S,6R)-2,6-dian-Anopimelinyl-D-alanine (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-Disoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200208)2002:16<2710::aid-ejoc2710>3.0.co;2-8

文献信息

• GlcNAc-1,6-anhydro-MurNAc Moiety Affords Unusual Glycosyl Acceptor that Terminates Peptidoglycan Elongation
  作者：Xiao-Lin Zhang、Gábor Báti、Chenyu Li、Aoxin Guo、Claresta Yeo、Han Ding、Kumar Bhaskar Pal、Yuan Xu、Yuan Qiao、Xue-Wei Liu

  DOI：10.1021/jacs.3c12526

  日期：2024.3.20

  that the incorporation of an anhydromuramyl-containing glycosyl acceptor by TGase into the growing PG may effectively inhibit PG elongation. To explore this possibility, we synthesized 4-O-(N-acetyl-β-d-glucosaminyl)-1,6-anhydro-N-acetyl-β-d-muramyl-l-Ala-γ-d-Glu-l-Lys-d-Ala-d-Ala, 1, within 15 steps, and demonstrated that this anhydromuropeptide and its analogue lacking the peptide, 1-deAA, were both

  肽聚糖（PG）是细菌中一种重要的外骨骼聚合物，是众所周知的抗生素靶标。 PG 聚合需要细菌转糖基酶 (TGase) 的作用，它将传入的糖基受体与供体偶联。干扰 TGase 活性会中断 PG 组装。现有的TGase抑制剂如莫诺霉素和Lipid II类似物总是占据TGase活性位点；其他干扰 PG 适当伸长的策略尚未得到广泛利用。受到细菌中标记 PG 链末端的天然 1,6-脱水-MurNAc 末端的启发，我们假设 TGase 将含有脱水胞壁酰基的糖基受体掺入生长的 PG 中可能会有效抑制 PG 延伸。为了探索这种可能性，我们合成了 4- O -( N -乙酰基-β- d -葡萄糖胺基)-1,6-anHydro- N -乙酰基-β- d -胞壁酰- l -Ala-γ- d -Glu- l -Lys -d -Ala- d -Ala, 1 ，在 15 个步骤内，并证明这种脱水壁肽及其缺乏肽的类似物1-deAA在体外均被细菌
• WO2020109792A5
  申请人：——

  公开号：WO2020109792A5

  公开（公告）日：2022-11-09
• Structure and stereochemistry of an anti-inflammatory anhydrosugar from the Australian marine sponge Plakinastrella clathrata and the synthesis of two analogues
  作者：Peter L. Katavic、Ken W.L. Yong、Joel N. Herring、Myrna A. Deseo、Joanne T. Blanchfield、Vito Ferro、Mary J. Garson

  DOI：10.1016/j.tet.2013.06.079

  日期：2013.9

  The structure and relative/absolute configuration of the C-15:0 iso-branched fatty acyl 1,6-anhydropyranose 1 isolated from the Australian marine sponge Plakinastrella clathrata have been investigated. Synthesis of the C-16:0 side chain-modified analogues 3 and 4 has enabled the relative configuration of the C-3 lactate moiety to be secured. In a preliminary anti-inflammatory screening, glycolipid 1 exhibited moderate activity in a PGE(2) inhibition assay, however, the compound showed no activity in cytotoxicity screening using 3T3 and P388 cell lines. (C) 2013 Elsevier Ltd. All rights reserved.
• 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.