N-benzoyl-D-mannosamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzoyl-D-mannosamine
• 英文别名: 2-benzamido-2-deoxy-D-mannopyranose；N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
• 化学式: C₁₃H₁₇NO₆
• 分子量: 283.281
• InChiKey: VSGKVJPCJOJUBP-JSCSOFAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzoyl-D-mannosamine 在 sodium azide 、 无机焦磷酸酶 、 sialic acid aldolase 、 α2,6-sialyltransferase from Photobacterium leiognathi JT-SHIZ-145 、 CMP-sialate synthetase from Neisseria meningitidis 、 magnesium chloride 、 alkaline phosphatase 作用下， 生成
  参考文献：
  名称：

  脑膜炎奈瑟氏球菌胞嘧啶-5'-单磷酸酯-N-乙酰神经氨酸合成酶（CMP-唾液酸合成酶）与底物结合的灵活性：新唾液酸结合物合成的催化剂

  摘要：

  我们已经成功建立了一个简单的连续比色测定法，可基于Neu5Ac或NPS核苷酸激活后释放的质子当量的pH值变化，对胞嘧啶5'-单磷酸酯-乙酰神经氨酸合成酶（CMP-唾液酸合成酶，CSS）活性进行灵敏可靠的定量分析。相关类似物。使用此方法，确定了脑膜炎奈瑟氏球菌CSS的稳态动力学数据，包括胞嘧啶5'-三磷酸（CTP），N-乙酰神经氨酸（Neu5Ac）和唾液酸的11种结构变异，包括主链截短，脱氨基，差向异构化，和几个N酰基修饰。这些数据进一步证明了脑膜炎奈瑟氏球菌具有非同寻常的多功能性CSS，用于一般访问包含非天然唾液酸类似物的唾液缀合物。引人注目的是，该测定法可以覆盖范围广泛的底物参数，这些参数涵盖了超过3个数量级的K M和k cat测量。借助基于X射线晶体结构数据构建的结构模型，动力学数据可用于解释Neu5Ac及其类似物在底物结合中的潜在蛋白质贡献。使用脑膜炎奈瑟氏球菌CSS和来自Photobacter的新型α2

  DOI：

  10.1002/adsc.201100412
• 作为产物：
  描述：

  2-苯甲酰胺基-2-脱氧-D-吡喃葡萄糖 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 96.0h， 生成 N-benzoyl-D-mannosamine
  参考文献：
  名称：

  Biological Properties of N-Acyl and N-Haloacetyl Neuraminic Acids: Processing by Enzymes of Sialic Acid Metabolism, and Interaction with Influenza Virus

  摘要：

  Several unnatural N-acyl neuraminic acids (N-propionyl, N-hexanoyl, N-benzoyl, N-trifluoroacetyl, N-chloroacetyl, N-difluoroacetyl) were prepared enzymatically using immobilised sialic acid aldolase. N-Trifluoroacetyl- N-chloroacetyl- and N-difluoroacetyl neuraminic acids were shown to enhance up to 10-fold the rate of association of influenza virus A to a sialoglycolipid neomembrane by surface plasmon resonance, and were found to act as weak inhibitors (K-iapp 0.45-2.0 mM) of influenza virus neuraminidase. The N-propionyl, N-chloroacetyl- and N-difluoroacetyl neuraminic acids were found to be substrates for recombinant Escherichia coli CMP sialate synthase, to give the corresponding CMP-N-acyl-neuraminic acids. CMP-N-propionyl neuraminic acid was found not to be a substrate for CMP-N-acetyl neuraminic acid hydroxylase from pig submandibular gland. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00213-4

文献信息

• One-Pot Enzymatic Synthesis and Biological Evaluation of Ganglioside GM3 Derivatives as Potential Cancer Immunotherapeutics
  作者：Juntao Wang、Dan Lu、Ran Sun、Shuwen Lei、Shuhua Luo、Xin Dang、Yang Zhang、Chang Yuan、Yong Zhang、Jinhong Wu、Guangyu Yang、Lei Fu、Faqin Jiang

  DOI：10.1021/acs.jmedchem.1c01301

  日期：2022.2.10

  worldwide. Recent research studies have revealed that GM3 derivatives have considerable promise as potential therapeutic agents for cancer. To discover novel GM3 derivatives as potential antitumor agents, a one-pot enzymatic synthesis was established, yielding 14 GM3 derivatives in high total yields (22–41%). Subsequently, the inhibitory activities of GM3 derivatives were assessed by wound-healing assays

  癌症是全世界死亡的主要原因。最近的研究表明，GM3 衍生物作为潜在的癌症治疗剂具有广阔的前景。为了发现新型 GM3 衍生物作为潜在的抗肿瘤药物，建立了一锅酶法合成方法，以高总产率 (22-41%) 产生了 14 种 GM3 衍生物。随后，通过伤口愈合试验和Transwell试验以及荷瘤动物模型评估了GM3衍生物的抑制活性。在所有GM3衍生物中， N-12在细胞中表现出优异的迁移和侵袭抑制作用，并且在C57BL/6小鼠中具有显着的抗肿瘤活性。随后对癌症组织和血清样本的分析表明， N-12可诱导肿瘤抑制，这与免疫反应密切相关。总而言之， N-12可以进一步开发为治疗癌症的有效疗法。然后进行 RNA 测序 (RNA-seq) 分析，结果表明N-12的抗肿瘤机制涉及粘着斑和 ECM-受体相互作用信号通路。
• Accessibility of N-acyl-d-mannosamines to N-acetyl-d-neuraminic acid aldolase
  作者：Yanbin Pan、Tiffany Ayani、Janos Nadas、Shouming Wen、Zhongwu Guo

  DOI：10.1016/j.carres.2004.05.028

  日期：2004.8

  N-Acetyl-D-neuraminic acid (NeuNAc) aldolase is an important enzyme for the metabolic engineering of cell-surface NeuNAc using chemically modified D-mannosamines. To explore the optimal substrates for this application, eight N-acyl derivatives Of D-mannosamine were prepared, and their accessibility to NcuNAc aldolase was quantitatively investigated. The N-propionyl-, N-butanoyl-, N-iso-butanoyl-, N-pivaloyl-, and N-phenylacetyl-D-mannosamines proved to be as good substrates as, or even better than, the natural N-acetyl-D-mannosamine, while the N-trifluoropropionyl and benzoyl derivatives were poor. It was proposed that the electronic effects might have a significant influence on the enzymatic aldol condensation reaction Of D-mannosamine derivatives, with electron-deficient acyl groups having a negative impact. The results suggest that N-propionyl-, N-butanoyl-, N-isobutanoyl-, and N-phenylacetyl-D-mannosamines may be employed to bioengineer NeuNAc on cells. (C) 2004 Elsevier Ltd. All rights reserved.
• Versatile intermediates in the selective modification of the amino function of 2-amino-2-deoxy-d-mannopyranose and the 3-position of 2-acetamido-2-deoxy-d-mannose: Potential membrane modifiers in neoplastic control
  作者：Norman J. Angelino、Ralph J. Bernacki、Moheswar Sharma、Onda Dodson-Simmons、Walter Korytnyk

  DOI：10.1016/0008-6215(95)00154-l

  日期：1995.10

  A general method has been developed to selectively modify the amino group of 2-amino-2-deoxy-D-mannopyranose (D-mannosamine), a precursor of the terminal membrane sugar, sialic acid. 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate was prepared via two routes that allowed introduction of various acyl groups onto the amino function. These compounds were evaluated for their antineoplastic properties. The most significant preclinical therapeutic finding was the antileukemic activity found in mice for tetra-O-acetyl-2-epi-streptozotocin (the acetylated alpha-mannosamine epimer of streptozotocin). Administration of 50 mg/kg/day X 5 to leukemia L1210-bearing DBA/2Ha mice resulted in 5/5 35-day survivors. Neutralization of 1,3,3,6-tetra-O-acetyl-2-amino-2-deoxy-alpha-D-mannopyranose oxalate under aqueous conditions led to 2-acetamido-1,4,6-tri-O-acetyl-2-deoxy-alpha-D-mannopyranose, the oxidation of which gave 2-acetamido-4,6-di-O-acetyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose. This agent demonstrated an IC50 of 25 mu M with a murine L1210 cell culture. Administration of 100 mg/kg/day X 5 resulted in 42% ILS in DBA/2 mice with ip L1210 leukemia. Several other nonacetylated derivatives were also prepared by direct N-acylation, producing, for example, fluorescently tagged N-dansylmannosamine.
• Biological Properties of N-Acyl and N-Haloacetyl Neuraminic Acids: Processing by Enzymes of Sialic Acid Metabolism, and Interaction with Influenza Virus
  作者：A Humphrey

  DOI：10.1016/s0968-0896(02)00213-4

  日期：2002.10

  Several unnatural N-acyl neuraminic acids (N-propionyl, N-hexanoyl, N-benzoyl, N-trifluoroacetyl, N-chloroacetyl, N-difluoroacetyl) were prepared enzymatically using immobilised sialic acid aldolase. N-Trifluoroacetyl- N-chloroacetyl- and N-difluoroacetyl neuraminic acids were shown to enhance up to 10-fold the rate of association of influenza virus A to a sialoglycolipid neomembrane by surface plasmon resonance, and were found to act as weak inhibitors (K-iapp 0.45-2.0 mM) of influenza virus neuraminidase. The N-propionyl, N-chloroacetyl- and N-difluoroacetyl neuraminic acids were found to be substrates for recombinant Escherichia coli CMP sialate synthase, to give the corresponding CMP-N-acyl-neuraminic acids. CMP-N-propionyl neuraminic acid was found not to be a substrate for CMP-N-acetyl neuraminic acid hydroxylase from pig submandibular gland. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Flexibility of Substrate Binding of Cytosine-5′-Monophosphate-N-Acetylneuraminate Synthetase (CMP-Sialate Synthetase) from Neisseria meningitidis: An Enabling Catalyst for the Synthesis of Neo-sialoconjugates
  作者：Ning He、Dong Yi、Wolf-Dieter Fessner

  DOI：10.1002/adsc.201100412

  日期：2011.9

  sensitive and reliable quantification of cytosine‐5′‐monophosphate‐acetylneuraminate synthetase (CMP‐sialate synthetase, CSS) activity based on the pH change of a released proton equivalent upon nucleotide activation of Neu5Ac or related analogues. Using this method, steady‐state kinetic data of Neisseria meningitidis CSS were determined for cytosine‐5′‐triphosphate (CTP), N‐acetylneuraminic acid (Neu5Ac)

  我们已经成功建立了一个简单的连续比色测定法，可基于Neu5Ac或NPS核苷酸激活后释放的质子当量的pH值变化，对胞嘧啶5'-单磷酸酯-乙酰神经氨酸合成酶（CMP-唾液酸合成酶，CSS）活性进行灵敏可靠的定量分析。相关类似物。使用此方法，确定了脑膜炎奈瑟氏球菌CSS的稳态动力学数据，包括胞嘧啶5'-三磷酸（CTP），N-乙酰神经氨酸（Neu5Ac）和唾液酸的11种结构变异，包括主链截短，脱氨基，差向异构化，和几个N酰基修饰。这些数据进一步证明了脑膜炎奈瑟氏球菌具有非同寻常的多功能性CSS，用于一般访问包含非天然唾液酸类似物的唾液缀合物。引人注目的是，该测定法可以覆盖范围广泛的底物参数，这些参数涵盖了超过3个数量级的K M和k cat测量。借助基于X射线晶体结构数据构建的结构模型，动力学数据可用于解释Neu5Ac及其类似物在底物结合中的潜在蛋白质贡献。使用脑膜炎奈瑟氏球菌CSS和来自Photobacter的新型α2