allyl 2-acetamido-2-deoxy-α-D-mannopyranoside | 140849-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-2-deoxy-α-D-mannopyranoside
• 英文别名: N-[(2S,3S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-prop-2-enoxyoxan-3-yl]acetamide
• CAS: 140849-88-3
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: GFLRLITULFAIEW-QGKZMRNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-2-deoxy-α-D-mannopyranoside 在 吡啶 、 sodium azide 、 sodium methylate 、 sodium acetate 、 溶剂黄146 、 sodium iodide 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 35.08h， 生成 2-acetamido-6-azido-2,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Overproduction of CMP-sialic acid synthetase for organic synthesis

  摘要：

  The gene coding for Escherichia coli CMP-sialic acid synthetase (E.C. 2.7.7.43) was cloned and overexpressed in E. coli through a primer-directed polymerase chain reaction. Two plasmids were constructed to produce the native enzyme and a modified enzyme fused with a decapeptide at the C-terminus. The decapeptide tag was used for detection of the enzyme production. Both enzymes produced from E. coli were isolated and purified with an Orange A dye resin and FPLC. Their properties were compared with respect to their kinetic parameters, stability, pH profiles, and substrate specificities. Both enzymes have similar k(cat) and K(m) for NeuAc and CTP but different pH profiles. Contrary to the native enzyme, the modified enzyme is more active at higher pH. Studies on specificity indicate that both enzymes have a high specific activity for C-9 modified NeuAc derivatives at neutral pH. Some C-5 modified (hydroxy, deoxy, and deoxyfluoro) NeuAc derivatives are not acceptable as substrates. The modified enzyme has been used in the synthesis of CMP-NeuAc from ManNAc and CMP and sialyl N-acetyllactosamine (Neu-alpha-2,6Gal-beta-1,4GlcNAc) with in situ generation of NeuAc and regeneration of CMP-NeuAc. The 6-O-acyl derivatives of ManNAc were prepared via transesterification in anhydrous dimethylformamide by using an engineered stable subtilisin variant as a catalyst, and the products were used as substrates in sialic acid aldolase-catalyzed synthesis of 9-O-acyl-NeuAc derivatives.

  DOI：

  10.1021/ja00036a044
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 14.5h， 生成 allyl 2-acetamido-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Overproduction of CMP-sialic acid synthetase for organic synthesis

  摘要：

  The gene coding for Escherichia coli CMP-sialic acid synthetase (E.C. 2.7.7.43) was cloned and overexpressed in E. coli through a primer-directed polymerase chain reaction. Two plasmids were constructed to produce the native enzyme and a modified enzyme fused with a decapeptide at the C-terminus. The decapeptide tag was used for detection of the enzyme production. Both enzymes produced from E. coli were isolated and purified with an Orange A dye resin and FPLC. Their properties were compared with respect to their kinetic parameters, stability, pH profiles, and substrate specificities. Both enzymes have similar k(cat) and K(m) for NeuAc and CTP but different pH profiles. Contrary to the native enzyme, the modified enzyme is more active at higher pH. Studies on specificity indicate that both enzymes have a high specific activity for C-9 modified NeuAc derivatives at neutral pH. Some C-5 modified (hydroxy, deoxy, and deoxyfluoro) NeuAc derivatives are not acceptable as substrates. The modified enzyme has been used in the synthesis of CMP-NeuAc from ManNAc and CMP and sialyl N-acetyllactosamine (Neu-alpha-2,6Gal-beta-1,4GlcNAc) with in situ generation of NeuAc and regeneration of CMP-NeuAc. The 6-O-acyl derivatives of ManNAc were prepared via transesterification in anhydrous dimethylformamide by using an engineered stable subtilisin variant as a catalyst, and the products were used as substrates in sialic acid aldolase-catalyzed synthesis of 9-O-acyl-NeuAc derivatives.

  DOI：

  10.1021/ja00036a044

文献信息

• NEOGLYCOCONJUGATES AS VACCINES AND THERAPEUTIC TOOLS
  申请人：KORANEX CAPITAL

  公开号：US20210085770A1

  公开（公告）日：2021-03-25

  Neoglycoconjugates as immunogens and therapeutic/diagnostic tools are described herein. The neoglycoconjugates are produced by conjugating a carbohydrate antigen intermediate to a free amine group of a carrier material (e.g., carrier protein). The intermediate comprises a linker having a first end and a second end, the first end being conjugated to a carbohydrate antigen via a thio ether bond and the second end comprising a functional group reactable with a free amine group. Following coupling, the carbohydrate antigen becomes covalently bound to the carrier material via an amide, a carbamate, a sulfonamide, a urea, or a thiourea bond, thereby producing the neoglycoconjugate. Applications of the neoglycoconjugates as antigens, immunogens, vaccines, and in diagnostics are also described. Specifically, the use of (neo)glycoconjugates as vaccine candidates and other therapeutic tools against cancers, viruses such as SARS-CoV-2, and other diseases characterized by expression of aberrant glycosylation are also described.

  新糖基共轭物作为免疫原和治疗/诊断工具在此进行描述。这些新糖基共轭物是通过将碳水化合物抗原中间体与载体材料（例如载体蛋白质）的自由胺基结合而产生的。该中间体包括具有第一端和第二端的连接物，第一端通过硫醚键与碳水化合物抗原结合，第二端包括可与自由胺基反应的功能基团。在偶联后，碳水化合物抗原通过酰胺、碳酸酯、磺酰胺、脲或硫脲键与载体材料共价结合，从而产生新糖基共轭物。还描述了将新糖基共轭物用作抗原、免疫原、疫苗和诊断的应用。具体地，还描述了将（新）糖基共轭物用作疫苗候选物和其他治疗工具，用于对抗癌症、冠状病毒（例如SARS-CoV-2）等病毒以及其他表达异常糖基化的疾病。
• The Conformation of the Mannopyranosyl Phosphate Repeating Unit of the Capsular Polysaccharide of<i>Neisseria meningitidis</i>Serogroup A and Its Carba-Mimetic
  作者：Ilaria Calloni、Luca Unione、Gonzalo Jiménez-Osés、Francisco Corzana、Linda Del Bino、Alessio Corrado、Olimpia Pitirollo、Cinzia Colombo、Luigi Lay、Roberto Adamo、Jesús Jiménez-Barbero

  DOI：10.1002/ejoc.201801003

  日期：2018.9.9

  Neisseria meningitidis serogroup A (MenA) is an aerobic diplococcal Gram‐negative bacterium responsible for epidemic meningitis disease. Its capsular polysaccharide (CPS) has been identified as the primary virulence factor of MenA. This polysaccharide suffers from chemical lability in water. Thus, the design and synthesis of novel and hydrolytically stable structural analogues of MenA CPS may provide

  脑膜炎奈瑟菌血清群 A (MenA) 是一种需氧双球菌革兰氏阴性菌，可导致流行性脑膜炎疾病。其荚膜多糖 (CPS) 已被确定为 MenA 的主要毒力因子。这种多糖在水中具有化学不稳定性。因此，MenA CPS 的新型水解稳定结构类似物的设计和合成可能为开发针对该疾病的疗法提供额外的工具。在这种情况下，对天然磷酸化单体的结构特征进行了分析，并将其与其碳水化合物类似物的结构特征进行了比较，其中环内氧已被亚甲基部分取代。使用量子力学技术和分子动力学模拟的组合计算了不同分子的最低能量几何形状。已使用核磁共振实验对预测结果进行了比较和验证。结果表明，更稳定的设计糖模拟物可能采用天然单体采用的构象，尽管它们在扭转自由度方面表现出更广泛的灵活性。
• Synthesis of Amino-Bridged Oligosaccharide Mimetics
  作者：Janna Neumann、Joachim Thiem

  DOI：10.1002/ejoc.200901106

  日期：2010.2

  Synthesis of amino-bridged oligosaccharides using reductive amination opens rapid access to novel glycomimetic target structures as potential ligands for the receptor protein NKR P1 of natural killer cells. Emphasis was laid on fast and facile synthetic routes. The carbonyl building blocks were easily obtained by oxidation with Dess-Martin periodinane or iodoxybenzoic acid (IBX). For the required

  使用还原胺化合成氨基桥连寡糖开辟了快速获取新的拟糖靶结构作为自然杀伤细胞受体蛋白 NKR P1 的潜在配体的途径。重点放在快速简便的合成路线上。通过用戴斯-马丁高碘烷或碘氧基苯甲酸 (IBX) 氧化很容易获得羰基结构单元。对于所需的氨基官能化单元，叠氮化物前体的还原是有利的，并且通过随后的还原胺化实现了新型寡糖的生成。目标糖类结构的特征是在两个非异头位置之间插入一个桥接氮原子，并包括一个异头位置。
• 2-acylamino-2-deoxy-glucono-1,5-lactones, a method for the production thereof, compositions containing them, and uses thereof
  申请人：——

  公开号：US20020028954A1

  公开（公告）日：2002-03-07

  The invention concerns compounds of formula (I) wherein: A represents R 1 or (O)R 1 where R 1 represents an alkyl group comprising 1 to 30 carbon atoms, linear or branched, saturated or unsaturated, capable of being partly or totally substituted by Hal where Hal represents —Cl, —Br, or —F, and of being interrupted by one or several units selected among —O—, —S—, —C(O)—, —NR 3 C(O)—, —Ph(R 4 ) n and —CH 2 —CH 2 —O) n —, wherein R 3 represents or —CH 2 ) n″ —CH where n″=0 to 17; R 4 represents, —CH 3 , —CH 2 H 5 , —C 3 H 7 and n=0 to 4 and n′=1, 2 or 3, or R 1 represents a cyclanic radical with diterpene or triterpene root; and R 2 represents a C 1 -C 11 linear or branched alkyl group. The invention also concerns a method for obtaining said compounds, compositions containing them and their use as surfactant, and in enzymatic processes using a chitinase, in particular N-acetylglucosaminidase.

  该发明涉及以下式(I)的化合物：其中：A代表R1或（O）R1，其中R1代表由1至30个碳原子组成的烷基基团，直链或支链，饱和或不饱和，可以部分或完全被Hal取代，其中Hal代表-Cl，-Br或-F，并且可以被选自-O-，-S-，-C(O)-，-NR3C(O)-，-Ph(R4)n和-CH2-CH2-O)n-的一个或多个单位中断，其中R3代表或-CH2)n″-CH2，其中n″=0至17；R4代表-CH3，-CH2H5，-C3H7和n=0至4，n′=1，2或3，或者R1代表带有二萜或三萜基团的环烷基基团；R2代表C1-C11直链或支链烷基基团。该发明还涉及一种获得所述化合物的方法，含有它们的组合物以及它们作为表面活性剂的用途，以及在使用壳聚糖酶，特别是N-乙酰葡萄糖氨基酶的酶促过程中的用途。
• Mutants of glycoside hydrolases and uses thereof for synthesizing complex oligosaccharides and disaccharide intermediates
  申请人：Institut Pasteur

  公开号：EP2100965A1

  公开（公告）日：2009-09-16

  Method for preparing the disaccharide α-D-glucopyranosyl-(1→4)-2-N-acetyl-2-deoxy-α-D-glucopyranoside, comprising the step of using a mutant of a wild type glycoside hydrolase.

  制备二糖α-D-葡萄糖苷-(1→4)-2-N-乙酰基-2-脱氧-α-D-葡萄糖苷的方法，包括使用野生型糖苷水解酶的突变体的步骤。