benzyl-N-acetyl-4,6-O-benzylidenemuramic acid | 87173-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: benzyl-N-acetyl-4,6-O-benzylidenemuramic acid
• 英文别名: (R)-2-{[(2S,4aR,6R,7R,8R,8aS)-7-Acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl]oxy}propanoic acid；(R)-2-(((2R,4aR,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid
• CAS: 87173-13-5
• 化学式: C₂₅H₂₉NO₈
• 分子量: 471.507
• InChiKey: JPPMVSNCFXDOJX-SKGCDESXSA-N

物化性质

• 沸点：
  717.7±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  benzyl-N-acetyl-4,6-O-benzylidenemuramic acid 在 palladium dihydroxide 4-二甲氨基吡啶 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  使用乙缩醛接头在固相支持物上制备潜在的Mur-pathway酶抑制剂。

  摘要：

  在这里，我们报告了mur-途径酶的潜在抑制剂的组合或并行固相合成的新策略。该策略涉及有效使用对烷氧基亚苄基乙缩醛接头将糖支架可逆地固定到固相。该方法用于以良好的产率合成固相上的几种糖肽。

  DOI：

  10.1016/s0960-894x(03)00043-x
• 作为产物：
  描述：

  苯甲醇 在 sodium hydride 、 对甲苯磺酸 、 原甲酸三乙酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 benzyl-N-acetyl-4,6-O-benzylidenemuramic acid
  参考文献：
  名称：

  A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

  摘要：

  糖醛醚化后接着进行叠氮硝化/还原，解决了在合成N-糖氧基muramyl二肽中的一个困难SN2步骤。

  DOI：

  10.1039/c4ob02147a

文献信息

• Synthesis of Functionalized <i>N</i>-Acetyl Muramic Acids To Probe Bacterial Cell Wall Recycling and Biosynthesis
  作者：Kristen E. DeMeester、Hai Liang、Matthew R. Jensen、Zachary S. Jones、Elizabeth A. D’Ambrosio、Samuel L. Scinto、Junhui Zhou、Catherine L. Grimes

  DOI：10.1021/jacs.8b03304

  日期：2018.8.1

  purification strategies to access large quantities of these PG building blocks, as well as their derivatives, are challenging. A robust chemoenzymatic synthesis was developed using an expanded NAM library to produce a variety of 2 -N-functionalized UDP NAMs. In addition, a synthetic strategy to access bio-orthogonal 3-lactic acid NAM derivatives was developed. The chemoenzymatic UDP synthesis revealed that the

  尿苷二磷酸 N-乙酰胞壁酸 (UDP NAM) 是细菌肽聚糖 (PG) 生物合成的关键中间体。作为塑造 PG 骨架的胞壁酸的主要来源，安装在 UDP NAM 中间体的修饰可用于通过代谢掺入选择性地标记和操纵该聚合物。然而，获取大量这些 PG 构建块及其衍生物的合成和纯化策略具有挑战性。使用扩展的 NAM 库开发了强大的化学酶合成，以产生各种 2-N-功能化的 UDP NAM。此外，还开发了一种获取生物正交 3-乳酸 NAM 衍生物的合成策略。化学酶促 UDP 合成表明，细菌细胞壁再循环酶 MurNAc/GlcNAc 异头激酶 (AMgK) 和 NAM α-1 磷酸尿苷转移酶 (MurU) 允许在糖供体的两个和三个位置进行排列。我们使用包括四嗪连接在内的各种生物正交化学进一步探索了这些衍生物在全细胞中革兰 (-) 和革兰 (+) PG 荧光标记中的效用。该报告允许快速和可扩展地访问各种功能化的
• Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments
  作者：Siavash Mashayekh、Klare L. Bersch、Jared Ramsey、Thomas Harmon、Benjamin Prather、Lauren A. Genova、Catherine L. Grimes

  DOI：10.1021/acs.joc.0c01852

  日期：2020.12.18

  bacterial cell wall. Fragments released from the PG serve as fundamental recognition elements for the immune system. The structure of the PG, however, encompasses a variety of chemical modifications among different bacterial species. Here, the applicability of organic synthetic methods to address this chemical diversity is explored, and the synthesis of cross-linked PG fragments, carrying biologically

  肽聚糖 (PG) 是细菌细胞壁的核心结构基序。从 PG 释放的片段是免疫系统的基本识别元件。然而，PG 的结构包含不同细菌物种之间的各种化学修饰。在这里，探讨了有机合成方法解决这种化学多样性的适用性，并使用溶液和固相方法介绍了带有生物相关氨基酸修饰和肽交联的交联 PG 片段的合成。
• Synthesis of a biologically active fluorescent muramyl dipeptide congener
  作者：C. K. Hiebert、W. C. Kopp、H. B. Richerson、C. F. Barfknecht

  DOI：10.1021/jm00366a014

  日期：1983.12

  A fluorescent-labeled muramyl dipeptide (MDP) has been prepared to probe immunoadjuvant cellular interactions. N-Acetylmuramyl-L-alanyl-D-isoglutamine (1) was synthesized in improved yield and reacted with 2-(fluoresceinylamino)-4,6-dichloro-s-triazine (DTAF, 2) to give the fluorescent adduct DTAF-MDP (3), attached through the 6-position of the sugar moiety. Adjuvant activity was assessed by using two different in vitro assays, macrophage spreading, and inhibition of macrophage migration. Both assays indicated that the apparent adjuvant activity of 3 is comparable to that of 1.
• Bacterial Derived Carbohydrates Bind Cyr1 and Trigger Hyphal Growth in <i>Candida albicans</i>
  作者：Jason M. Burch、Siavash Mashayekh、Dennis D. Wykoff、Catherine L. Grimes

  DOI：10.1021/acsinfecdis.7b00154

  日期：2018.1.12

  The dimorphic yeast Candida albicans is the most common pathogenic fungus found in humans. While this species is normally commensal, a morphological switch from budding yeast to filamentous hyphae allows the fungi to invade epithelial cells and cause infections. The phenotypic change is controlled by the adenylyl cyclase, Cyrl. Interestingly, this protein contains a leucine-rich repeat (LRR) domain, which is commonly found in innate immune receptors from plants and animals. A functional and pure LRR domain was obtained in high yields from E. coli expression. Utilizing a surface plasmon resonance assay, the LRR was found to bind diverse bacterial derived carbohydrates with high affinity. This domain is capable of binding fragments of peptidoglycan, a carbohydrate polymer component of the bacterial cell wall, as well as anthracyclines produced by Streptomyces, leading to hyphae formation. These findings add another dimension to the human microbiome, taking into account yeast bacteria interactions that occur in the host.