烯丙基2,3,4,6-四-O-乙酰基-ALPHA-D-吡喃甘露糖苷 | 119111-31-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 烯丙基2,3,4,6-四-O-乙酰基-ALPHA-D-吡喃甘露糖苷
• 英文名称: allyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: Allyl 2,3,4,6-tetra-O-acetyl-a-D-mannopyranoside；[(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 119111-31-8
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: CRUHDGOVWKFJBM-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  烯丙基2,3,4,6-四-O-乙酰基-ALPHA-D-吡喃甘露糖苷 在 sodium methylate 、 对甲苯磺酸 水 、 溶剂黄146 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.0h， 生成 allyl 2,3-O-isopropylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of β-d-Galp-(1→4)-α-d-Manp methanephosphonate, a substrate analogue for the elongating α-d-mannosyl phosphate transferase in the Leishmania

  摘要：

  An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00961-3
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 溶剂黄146 、 silver(l) oxide 、 肼 作用下， 以 甲苯 为溶剂， 反应 111.0h， 生成 烯丙基2,3,4,6-四-O-乙酰基-ALPHA-D-吡喃甘露糖苷
  参考文献：
  名称：

  Synthesis of allyl 2-O-(α-l-arabinofuranosyl)-6-O-(α-d-mannopyranosyl)-β-d-mannopyranoside, a unique plant N-glycan motif containing arabinose

  摘要：

  The synthesis of the trisaccharide allyl 2-O-(alpha -L-arabinofuranosyl)-6-O-(alpha -D-mannopyranosyl)-beta -D-mannopyranoside is reported. Stereoselective glycosylation at C-6 of a non-protected allyl beta -mannoside with the acetylated alpha -D-mannosyl bromide gave the alpha-(1 --> 6)-disaccharide as the main product and the crystalline 3,6-branched trisaccharide as minor compound. Further glycosylation of the 2,3 diol (1 --> 6) disaccharide with L-arabinofuranosyl bromide furnished a mixture of 3-O- and 2-O-alpha -L-Ara-trisaccharides from which the title compound was isolated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00185-3

文献信息

• Developing a Library of Mannose-Based Mono- and Disaccharides: A General Chemoenzymatic Approach to Monohydroxylated Building Blocks
  作者：Lisa Tanzi、Marina Simona Robescu、Sara Marzatico、Teresa Recca、Yongmin Zhang、Marco Terreni、Teodora Bavaro

  DOI：10.3390/molecules25235764

  日期：——

  position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently

  通过酶水解实现了异头位置不同官能化的乙酰化甘露糖基单糖和二糖的区域选择性脱保护。假丝酵母脂肪酶 (CRL) 和短小芽孢杆菌乙酰木聚糖酯酶 (AXE) 分别固定在辛基琼脂糖和乙醛糖琼脂糖上。生物催化剂的区域选择性受糖结构和异头位置的官能化影响。通常，CRL 能够催化 C6 位乙酰化单糖的区域选择性脱保护。当乙酰化二糖用作底物时，AX 表现出对 C2 或 C6 位置的显着偏好，当 C2 参与糖苷键时。通过在活性和区域选择性方面为每种底物选择最佳酶，
• Synthesis of Benzaldehyde-Functionalized Glycans: A Novel Approach Towards Glyco-SAMs as a Tool for Surface Plasmon Resonance Studies
  作者：Sebastian Kopitzki、Knud J. Jensen、Joachim Thiem

  DOI：10.1002/chem.200902693

  日期：——

  In recent years the interest in tools for investigating carbohydrate–protein (CPI) and carbohydrate‐carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self‐assembled monolayers (SAM) of

  近年来，人们对研究碳水化合物-蛋白质（CPI）和碳水化合物-碳水化合物相互作用（CCI）的工具的兴趣大大增加。为了调查CPI和CCI，可以使用几种采用不同链接方法的技术。表面等离振子共振（SPR）成像是分析碳水化合物衍生物可模仿糖萼的自组装单分子膜（SAM）形成的最合适工具。与先前用于分析CPI和CCI的SPR成像方法相反，本文报道的新颖方法可轻松，快速地合成接头间隔子和碳水化合物衍生物，并通过控制配体的数量和方向来增强结合作用。为了通过还原胺化固定在具有生物排斥性的氨基官能化SPR芯片上，已通过包括烯烃复分解在内的几个简便步骤合成了多种醛官能化的聚糖结构（葡萄糖，半乳糖，甘露糖，葡糖胺，纤维二糖，乳糖和乳糖胺）。提出了针对凝集素伴刀豆球蛋白A的有效固定方法和首次结合研究。
• Total Synthesis of a Glycosylphosphatidylinositol Anchor of the Human Lymphocyte CD52 Antigen
  作者：Srinivas Burgula、Benjamin M. Swarts、Zhongwu Guo

  DOI：10.1002/chem.201102545

  日期：2012.1.23

  The first total synthesis of a glycosylphosphatidylinositol (GPI) anchor bearing a polyunsaturated arachidonoyl fatty acid is reported. This lipid is found in mammalian GPIs that do not undergo lipid remodeling, a process that has important implications in the localization and function of GPI‐anchored proteins. Incorporation of the oxidation‐ and reduction‐sensitive arachidonoyl lipid in the target

  报道了第一个全合成糖基磷脂酰肌醇 (GPI) 锚的多不饱和花生四烯酸脂肪酸。这种脂质存在于不经历脂质重塑的哺乳动物 GPI 中，这一过程对 GPI 锚定蛋白的定位和功能具有重要意义。通过使用对甲氧基苄基 (PMB) 基团进行永久羟基保护，将氧化和还原敏感的花生四烯酸脂质掺入目标 GPI 中，该基团具有选择性、快速和有效的全局脱保护协议。这种合成策略的灵活性通过在人淋巴细胞 CD52 抗原的 GPI 锚中包含两个额外的 GPI 核心结构修饰而得到进一步强调。
• [EN] CONJUGATE BASED SYSTEMS FOR CONTROLLED INSULIN DELIVERY<br/>[FR] SYSTÈMES À BASE DE CONJUGUÉS POUR L'ADMINISTRATION CONTRÔLÉE D'INSULINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2019125878A1

  公开（公告）日：2019-06-27

  The present disclosure provides conjugates that comprise an insulin molecule conjugated via a conjugate framework to two or more separate ligands that each include a saccharide, wherein the framework, ligand, saccharide and insulin molecule optionally comprise a fatty chain (e.g., a C8-30 fatty chain), wherein when said insulin molecule is conjugated both to a C8-30 fatty chain and one or more separate ligands that each include a saccharide, said C8-30 fatty chain is linked to insulin molecule only, and wherein when the framework or ligand comprises a fatty chain the insulin molecule is conjugated to two or more separate ligands. In certain embodiments, a conjugate is characterized in that, when the conjugate is administered to a mammal, at least one pharmacokinetic (PK) and/or pharmacodynamic (PD) property of the conjugate is sensitive to serum concentration of a second saccharide. In certain embodiments, a conjugate is also characterized by having a protracted PK profile. Exemplary conjugates and sustained release formulations are provided in addition to methods of use and preparation.

  本公开提供了包含胰岛素分子通过一个共轭框架与两个或更多个单独的配体结合的共轭物，每个配体都包括一个糖苷的共轭物，其中该框架、配体、糖苷和胰岛素分子可选择包括一个脂肪链（例如，一个C8-30脂肪链），当所述胰岛素分子既与一个C8-30脂肪链结合又与一个或多个包括糖苷的单独的配体结合时，所述C8-30脂肪链仅与胰岛素分子连接，当该框架或配体包括一个脂肪链时，胰岛素分子与两个或更多个单独的配体结合。在某些实施例中，一个共轭物的特征在于，当将该共轭物注射给哺乳动物时，该共轭物的至少一个药代动力学（PK）和/或药效动力学（PD）特性对第二糖苷的血清浓度敏感。在某些实施例中，一个共轭物还具有持续的PK特性。除了使用和制备方法外，还提供了示例共轭物和缓释制剂。
• Acid‐Assisted Direct Olefin Metathesis of Unprotected Carbohydrates in Water
  作者：Brian J. J. Timmer、Olof Ramström

  DOI：10.1002/chem.201903155

  日期：2019.11.13

  The ability to use unprotected carbohydrates in olefin metathesis reactions in aqueous media is demonstrated. By using water-soluble, amine-functionalized Hoveyda-Grubbs catalysts under mildly acidic aqueous conditions, the self-metathesis of unprotected alkene-functionalized α-d-manno- and α-d-galactopyranosides could be achieved through minimization of nonproductive chelation and isomerization. Cross-metathesis

  证明了在水性介质中的烯烃复分解反应中使用未保护的碳水化合物的能力。通过在弱酸性水溶液条件下使用水溶性，胺官能化的Hoveyda-Grubbs催化剂，可以通过最大限度地减少非生产性螯合和异构化来实现未保护的烯烃官能化的α-d-甘露聚糖和α-d-吡喃半乳糖苷的自易位。 。与烯丙醇的交叉复分解也可以以合理的选择性实现。少量（2.5体积％）的乙酸的存在增加了自易位产物的形成，同时显着减少了烯烃的异构化过程。此外，在大量（0.01 mm）蛋白质存在下，催化活性得以保留，强调了在生物条件下这种碳-碳键形成反应的潜力。这些结果证明了在与生物系统相容的温和条件下在烯烃复分解反应中直接使用未保护的碳水化合物结构的潜力，从而使其能够用于例如药物发现和蛋白质衍生化。