1,3,4-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-mannopyranoside | 74984-94-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-mannopyranoside
• 英文别名: [(2R,3S,4R,5S,6R)-5-acetamido-4,6-diacetyloxy-2-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 74984-94-4
• 化学式: C₁₄H₂₁NO₉
• 分子量: 347.322
• InChiKey: VMFNIHQAYQFWOI-ITGHMWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3,4-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-mannopyranoside 在 5-(乙硫基)-1H-四唑 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.42h， 生成
  参考文献：
  名称：

  用于受控代谢工程的光释放聚糖前体的合成和哺乳动物细胞相容性

  摘要：

  向生物分子或聚糖添加糖是生物学中最丰富的生物分子修饰之一，因为它们使细胞能够适应不断变化的营养和压力条件。糖生物学领域尚未解决的挑战是研究具有化学控制的聚糖生物合成途径，尤其是在活细胞环境中。本研究的目的是创建具有受控释放特性的生物相容性聚糖前体。在这里，我们报告了 11 个“笼式”糖探针，它们在光照下释放聚糖生物合成前体分子。我们用探针靶向的特定糖途径调节N的添加-乙酰糖 GlcNAc、GalNAc 和唾液酸到细胞中的生物分子上，其中每一种都有可能改变涉及细胞形态、信号和行为的聚糖过程。我们假设我们的聚糖前体探针将保持生物学惰性，直到满足光引发的降解条件，从而避免包括新陈代谢和细胞毒性在内的生物活动。GlcNAc、GalNAc 和 ManNAc（唾液酸前体）糖的光笼类似物，我们称之为“光糖”，在最佳波长的光照下几分钟内释放。在研究过程中，我们描述了这些糖在各自降解条件下的细胞相容性，并发现了高度细胞相容的

  DOI：

  10.1016/j.bmc.2022.116918
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 在 吡啶 、 iron(III) chloride hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1,3,4-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  用于受控代谢工程的光释放聚糖前体的合成和哺乳动物细胞相容性

  摘要：

  向生物分子或聚糖添加糖是生物学中最丰富的生物分子修饰之一，因为它们使细胞能够适应不断变化的营养和压力条件。糖生物学领域尚未解决的挑战是研究具有化学控制的聚糖生物合成途径，尤其是在活细胞环境中。本研究的目的是创建具有受控释放特性的生物相容性聚糖前体。在这里，我们报告了 11 个“笼式”糖探针，它们在光照下释放聚糖生物合成前体分子。我们用探针靶向的特定糖途径调节N的添加-乙酰糖 GlcNAc、GalNAc 和唾液酸到细胞中的生物分子上，其中每一种都有可能改变涉及细胞形态、信号和行为的聚糖过程。我们假设我们的聚糖前体探针将保持生物学惰性，直到满足光引发的降解条件，从而避免包括新陈代谢和细胞毒性在内的生物活动。GlcNAc、GalNAc 和 ManNAc（唾液酸前体）糖的光笼类似物，我们称之为“光糖”，在最佳波长的光照下几分钟内释放。在研究过程中，我们描述了这些糖在各自降解条件下的细胞相容性，并发现了高度细胞相容的

  DOI：

  10.1016/j.bmc.2022.116918

文献信息

• [EN] MONOSACCHARIDE PHOSPHORAMIDATE PRODRUGS<br/>[FR] PROMÉDICAMENTS À BASE DE PHOSPHORAMIDATE DE MONOSACCHARIDE
  申请人：CERECOR INC

  公开号：WO2019118486A1

  公开（公告）日：2019-06-20

  The present disclosure provides monosaccharide phosphoramidate prodrugs of monosaccharide monophosphates. The present disclosure further provides methods of treating diseases of conditions such as congenital disorders of glycosylation comprising administering the monosaccharide phosphoramidate prodrugs of the present disclosure to a patient in need thereof.

  本公开提供了单糖磷酰胺酯前药，用于单糖单磷酸。本公开还提供了治疗糖基化先天性疾病等疾病或症状的方法，包括向需要的患者施用本公开的单糖磷酰胺酯前药。
• Non-mucin type synthetic compounds or its carrier conjugated compounds
  申请人：KOTOBUKI PHARMACEUTICAL CO., LTD.

  公开号：US20020107224A1

  公开（公告）日：2002-08-08

  The purposes of this invention are preparation of the non-mucin type synthetic compounds-carrier conjugated compounds which are stable against enzymes, and which have the ability of specific reactivity to induce immune response for cancer and HIV. A compound of the general formula (1), 1 wherein A represents OH or sialic acid and/or it's derivatives, and B represents OH or galactose and/or it's derivatives; T represents H or protecting groups of amine; M represents H or OH; X represents oxygen atom, —NH— or S(O)z (where z is 0, 1 or 2); Q is H or oxygen atom; V represents lower alkyl or H; W is straight or branched alkylene groups from 0 to 5; Z is straight or branched alkylene groups from 1 to 5; i, m, and t is 0 or 1; non-mucin type synthetic compounds or it's carrier conjugated compounds, which have above mentioned compounds as a core structure of antigen.

  该发明的目的是制备稳定于酶的非黏液型合成化合物-载体偶联化合物，具有特异性反应能力，诱导癌症和HIV免疫反应。通式（1）的化合物，其中A代表OH或唾液酸及其衍生物，B代表OH或半乳糖及其衍生物；T代表氨基的保护基或H；M代表OH或H；X代表氧原子，-NH-或S（O）z（其中z为0、1或2）；Q为H或氧原子；V代表较低的烷基或H；W为直链或支链的0至5个碳原子的烷基基团；Z为直链或支链的1至5个碳原子的烷基基团；i、m和t为0或1；非黏液型合成化合物或其载体偶联化合物，其具有上述化合物作为抗原的核心结构。
• Targeting GNE Myopathy: A Dual Prodrug Approach for the Delivery of <i>N</i>-Acetylmannosamine 6-Phosphate
  作者：Chiara Morozzi、Jana Sedláková、Michaela Serpi、Marialuce Avigliano、Rosangela Carbajo、Lucia Sandoval、Yadira Valles-Ayoub、Patrick Crutcher、Stephen Thomas、Fabrizio Pertusati

  DOI：10.1021/acs.jmedchem.9b00833

  日期：2019.9.12

  ProTides comprise an important class of prodrugs currently marketed and developed as antiviral and anticancer therapies. The ProTide technology employs phosphate masking groups capable of providing more favorable druglike properties and an intracellular activation mechanism for enzyme-mediated release of a nucleoside monophosphate. Herein, we describe the application of phosphoramidate chemistry to 1,3,4-O-acetylated N-acetylmannosamine (Ac(3)ManNAc) to deliver ManNAc-6-phosphate (ManNAc-6-P), a critical intermediate in sialic acid biosynthesis. Sialic acid deficiency is a hallmark of GNE myopathy, a rare congenital disorder of glycosylation (CDG) caused by mutations in GNE that limit the production of ManNAc-6-P. Synthetic methods were developed to provide a library of Ac(3)ManNAc-6-phosphoramidates that were evaluated in a series of studies for their potential as a treatment for GNE myopathy. Prodrug 12b showed rapid activation in a carboxylesterase (CPY) enzymatic assay and favorable ADME properties, while also being more effective than ManNAc at increasing sialic acid levels in GNE-deficient cell lines. These results provide a potential platform to address substrate deficiencies in GNE myopathy and other CDGs.
• Comparison of chemical and enzymatic synthesis of 2-acetamido-2-deoxy-d-mannose 6-phosphate: a new approach
  作者：Mei-Zheng Liu、Yuan C. Lee

  DOI：10.1016/s0008-6215(00)00299-8

  日期：2001.2

  Chemical and enzymatic methods to synthesis of 2-acetamido-2-deoxy-D-mannose-6-phosphate (ManNAc-6-P) have been investigated. A new preparative method has been developed although some established procedures were tried. In this new method, a 6-O-acetyl or 4,6-di-O-acetyl group of the per-O-acetylated 2-acetamido-2-deoxy-D-mannose (ManNAc) were regioselectively removed with an esterase from the yellow yeast, Rhonosporidium toruloides, followed by phosphorylation and O-deacetylation under mild conditions. H-1 and C-13 NMR data spectra of ManNAc-6-P were recorded. (C) 2001 Elsevier Science Ltd. All rights reserved.
• US6858724B2
  申请人：——

  公开号：US6858724B2

  公开（公告）日：2005-02-22