Methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate | 119241-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate
• 英文别名: methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-D-galactononulopyranosonate；methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-galactononulopyranosonate；methyl N-acetyl-α-D-neuraminate；N'-acetylneuraminic acid methyl ester；methyl (2S,4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2S)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 119241-61-1
• 化学式: C₁₂H₂₁NO₉
• 分子量: 323.3
• InChiKey: BKZQMWNJESHHSA-JKYMVTTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.78
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  165.78
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate 在 sodium hydroxide 、 2,4,6-三异丙基苯磺酰氯 作用下， 以 吡啶 、 水 为溶剂， 反应 22.0h， 生成 5-acetamido-3,5-dideoxy-9-methylphosphono-β-D-glycero-D-galactononulopyranosidonic acid
  参考文献：
  名称：

  唾液酸衍生物的合成和酶促掺入，用作研究糖蛋白和其他糖缀合物的结构，活性和抑制作用的工具。

  摘要：

  已经开发出用于酶促合成唾液酸部分中含有重金属汞或流感C 9-O-乙酰基神经氨酸酯酶催化的过渡态类似物膦酸酯的复杂碳水化合物和糖蛋白的酶促方法。5-Acetamido-3，5-dideoxy-9-methylphosphono-beta-D-glycero-D-galacto-nonulopyra nosidonic acid（1），5-acetamido-3,5-dideoxy-9-methylphosphono-2-propyl-alpha -D-甘油-D-半乳糖-壬基吡喃二磺酸三乙基铵盐（2）和5-乙酰氨基-9-硫代甲基汞-3、5,9-苯氧基-β-D-甘油-D-半乳糖-壬基吡喃二磺酸（3）是合成的。化合物1和2是对C型流感病毒的结合和感染至关重要的酯酶的过渡态抑制剂。

  DOI：

  10.1016/s0968-0896(98)00121-7
• 作为产物：
  描述：

  5-acetamido-3,5-dideoxy-L-glycero-L-altro-2-nonulopyranosonic acid 生成 Methyl 5-acetamido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate
  参考文献：
  名称：

  ZBIRAL, ERICH;SCHREINER, ERWIN;SALUNKHE, MAMIKRAO M.;SCHULZ, GERHARD;KLEI+, LIEBIGS ANN. CHEM.,(1989) N, C. 519-526

  摘要：

  DOI：

文献信息

• Phase-transfer-catalyzed synthesis of aryl α-ketosides of N-acetylneuraminic acid. A 2-methylfluoran-6-yl glycoside of N-acetylneuraminic acid, 2-methyl-6-(5-acetamido-3,5-dideoxy-α-d-glycero-d-galacto-nonulopyranosyl-onic acid)xanthene-9-spiro-1′-isobenzofuran-3′-one, a new substrate for neuraminidase assay
  作者：Jörg Rothermel、Hans Faillard

  DOI：10.1016/0008-6215(90)84104-3

  日期：1990.2

  catalysis in chloroform-aqueous alkali gave several known and some new aryl alpha-ketosides in a short reaction time and in good yields. The 4-methylumbelliferyl alpha-ketoside, the standard substrate for neuraminidase, was prepared in a yield of up to 70%. New Neu5Ac ketosides were prepared with fluorescein and the fluorescein analog, 2-methyl-6-hydroxyfluoran (2-methyl-6-hydroxyxanthene-9-spiro-1'-isobenzofuran-3'-one)

  通过在氯仿-水溶液中的相转移催化对N-乙酰神经氨酸进行糖苷化反应，可以在较短的反应时间内以高收率得到几种已知的和一些新的芳基α-酮苷。制备了神经氨酸酶的标准底物4-甲基伞形酮基α-酮基，产率最高为70％。用荧光素和荧光素类似物2-甲基-6-羟基荧烷（2-甲基-6-羟基氧杂蒽-9-螺基-1'-异苯并呋喃-3'-one）作为糖苷配基制备了新的Neu5Ac酮苷。 2-（2-羟基-5-甲基-苯甲酰基）苯甲酸和3-氟苯酚。α构型通过400-MHz 1H-nmr光谱法和通过用霍乱弧菌和产气荚膜梭菌的神经氨酸酶裂解酮苷来确定。
• Selective Exo-Enzymatic Labeling of N-Glycans on the Surface of Living Cells by Recombinant ST6Gal I
  作者：Ngalle Eric Mbua、Xiuru Li、Heather R. Flanagan-Steet、Lu Meng、Kazuhiro Aoki、Kelley W. Moremen、Margreet A. Wolfert、Richard Steet、Geert-Jan Boons

  DOI：10.1002/anie.201307095

  日期：2013.12.2

  A game of tag: N‐Glycans on the surface of living cells were selectively tagged by exogenously administering recombinant ST6Gal I sialyltransferase and azide‐modified CMP‐Neu5Ac. This modification was followed by a strain‐promoted cycloaddition using a biotin‐modified dibenzylcyclooctynol (red star=biotin). The methodology will make it possible to dissect the mechanisms that underlie altered glycoconjugate

  标签游戏：通过外源施用重组 ST6Gal I 唾液酸转移酶和叠氮化物修饰的 CMP-Neu5Ac，选择性标记活细胞表面的 N-聚糖。这种修饰之后是使用生物素修饰的二苄基环辛炔醇（红星=生物素）进行菌株促进的环加成。该方法将使剖析疾病中糖复合物回收和储存改变的机制成为可能。
• Syntheses of alkenylated carbohydrate derivatives toward the preparation of monolayers on silicon surfaces
  作者：Louis C.P.M. de Smet、Aliaksei V. Pukin、Gerrit A. Stork、C.H. Ric de Vos、Gerben M. Visser、Han Zuilhof、Ernst J.R. Sudhölter

  DOI：10.1016/j.carres.2004.09.004

  日期：2004.10

  This note describes the synthesis of different alkenylated carbohydrate derivatives suitable for direct attachment to hydrogen-terminated silicon surfaces. The derivatives were alkenylated at the C-1 position, while the remaining hydroxyl groups were protected. The development of such new carbohydrate-based sensing elements opens the access to new classes of biosensors. (C) 2004 Elsevier Ltd. All rights reserved.
• Zbiral, Erich; Schreiner, Erwin; Salunkhe, Mamikrao M., Liebigs Annalen der Chemie, 1989, p. 519 - 526
  作者：Zbiral, Erich、Schreiner, Erwin、Salunkhe, Mamikrao M.、Schulz, Gerhard、Kleineidam, Reinhard G.、Schauer, Roland

  DOI：——

  日期：——
• Synthesis and inhibitory properties of a thiomethylmercuric sialic acid with application to the X-ray structure determination of 9- O -acetylsialic acid esterase from influenza C virus
  作者：Wolfgang Fitz、Peter B. Rosenthal、Chi-Huey Wong

  DOI：10.1016/0968-0896(96)00123-x

  日期：1996.8

  2-alpha-Thiomethylmercuryl 9-acetamido-9-deoxy-sialoside was prepared and found to inhibit the 9-O-acetylsialic acid esterase from influenza C virus in a competitive manner with a K-i of 4.2 +/- 0.5 mM. The inhibitor is being used in the X-ray determination of the crystal structure of the esterase. Copyright (C) 1996 Elsevier Science Ltd